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苄基芳基醚重排催化反应的研究进展

王重庆,  马宁宁,  杨超,  刘世豪,  朱驹,  郑灿辉

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王重庆, 马宁宁, 杨超, 刘世豪, 朱驹, 郑灿辉. 苄基芳基醚重排催化反应的研究进展[J]. 药学实践与服务, 2015, 33(6): 486-489. doi: 10.3969/j.issn.1006-0111.2015.06.002
引用本文: 王重庆, 马宁宁, 杨超, 刘世豪, 朱驹, 郑灿辉. 苄基芳基醚重排催化反应的研究进展[J]. 药学实践与服务, 2015, 33(6): 486-489. doi: 10.3969/j.issn.1006-0111.2015.06.002
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WANG Chongqing, MA Ningning, YANG Chao, LIU Shihao, ZHU Ju, ZHENG Canhui. Research progress in the catalytic rearrangement reaction of benzyl phenyl ethers[J]. Journal of Pharmaceutical Practice and Service, 2015, 33(6): 486-489. doi: 10.3969/j.issn.1006-0111.2015.06.002
Citation: WANG Chongqing, MA Ningning, YANG Chao, LIU Shihao, ZHU Ju, ZHENG Canhui. Research progress in the catalytic rearrangement reaction of benzyl phenyl ethers[J]. Journal of Pharmaceutical Practice and Service, 2015, 33(6): 486-489. doi: 10.3969/j.issn.1006-0111.2015.06.002
shu

苄基芳基醚重排催化反应的研究进展

doi: 10.3969/j.issn.1006-0111.2015.06.002
  • 1.

    第二军医大学药学院药物化学教研室, 上海 200433

  • 2.

    总后直属供应保障局门诊部, 北京 100071

Research progress in the catalytic rearrangement reaction of benzyl phenyl ethers

  • 1.

    Department of Medicinal Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, China

  • 2.

    Outpatient Department, Supply and Support Division of General Logistics Department of PLA, Beijing 100071, China

  • 摘要: 苄基芳基醚(BPE)的重排反应在有机化学和药物合成中具有重要作用。综述BPE在三氟乙酸、磷钨酸、环糊精、熔融锡和三溴化铝等不同催化体系中的重排反应,并探讨其可能的反应机制。
    Abstract: The rearrangement reaction of benzyl phenyl ethers(BPE) plays an important role in the organic chemistry and drug synthesis. This paper briefly reviewed the rearrangement reaction and its possible mechanism in various catalytic systems, such as trifluoroacetic acid, phosphotungstic acid, cyclodextrin, molten tin and aluminium bromide.
  • [1] Hartmann C, Gattermann L. Ueber die verseifung von phenoläthern und derivaten derselben, sowie von s ure thern durch aluminiumchlorid[J]. Eur J Inorg Chem, 1892, 25(2): 3531-3534.
    [2] Sagrera G, Seoane G. Acidic rearrangement of (benzyloxy)chalcones: a short synthesis of chamanetin[J]. Synthesis, 2009, 24: 4190-4202.
    [3] Petchmanee T, Ploypradith P, Ruchirawat S, et al. Solid-supported acids for debenzylation of aryl benzyl ethers[J]. J Org Chem, 2006, 71(7): 2892-2895.
    [4] Bhure MH, Rode CV, Chikate RC, et al. Phosphotungstic acid as effcient solid catalyst for intramolecular rearrangement of benzyl phenyl ether to 2-benzyl phenol[J]. Catal Commun, 2007, 8: 139-144.
    [5] Rode CV, Garade AC, Chikate RC. Solid acid catalysts: modification of acid sites and effect on activity and selectivity tuning in various reactions[J]. Catal Surv Asia, 2009,13:205-220.
    [6] Khabnadideh S, Pez D, Musso A, et al. Design, synthesis and evaluation of 2,4-diaminoquinazolines as inhibitors of trypanosomal and leishmanial dihydrofolate reductase[J]. Bioorg Med Chem, 2005, 13(7): 2637-2649.
    [7] Pitchumani K, Devanathan S, Ramamurthy V. Modification of photochemical reactivity on formation of inclusion complexes: photorearrangement of benzyl phenyl ethers and methyl phenoxyacetates[J]. J Photochem Photobiol A:Chem, 1992, 69: 201-208.
    [8] Ramamurthy V. Organic photochemistry in organized media[J]. Tetrahedron, 1986, 42(21): 5753-5839.
    [9] Kelly DP, Pinhey JT. The photochemical rearrangement of phenoxyacetic acids[J]. Tetrahedron Lett, 1964, 46(5): 3427-3429.
    [10] Ozawa S, Suenaga T, Ogino Y. Effects of molten tin surface upon the reaction of benzyl phenyl ether[J]. Fuel, 1985, 64(5): 712-714.
    [11] Shimamura N, Sugimori A. Direct and sensitized photoreactions of allyl phenyl ether[J]. Bull Chem Soc Jpn, 1971, 44(1): 281-283.
    [12] Xu JQ, George M, Weiss RG. Photo-fries rearrangements of 1-naphthyl (R)-2-phenylpropanoate in poly(vinyl acetate) and ethyl acetate. Influence of medium polarity and polymer relaxation on motions of singlet radical pairs[J]. Ann Braz Acad Sci, 2006, 78(1): 31-44.
    [13] Tarbell DS,Petropoulos JC. The action of aluminum bromide on benzyl phenyl ether[J]. J Am Chem Soc, 1952, 74(5): 244-248.
    [14] Hart H, Eleuterio HS . The stereochemistry of aromatic alkylations II. the thermal rearrangement of alkyl aryl ethers[J]. J Am Chem Soc, 1954, 76(2): 519-522.
    [15] Hart LS, Waddington CR. Aromatic rearrangements in the benzene series. Part 4. intramolecularity of both the ortho- and para-rearrangements of benzyl phenyl ether as shown by labelling experiments[J]. J Chem Soc, 1985,Perkin Trans II:1607-1612.
    [16] Hart H,Kosak JR. Stereochemical control by solvent in the thermal rearrangement of aryl α-phenethyl ethers[J]. J Org Chem, 1958, 23: 2019-2020.
    [17] Dewar MJS, Pierini AB. Mechanism of the diels-alder reaction. Studies of the addition of maleic anhydride to furan and methylfurans[J]. J Am Chem Soc, 1984, 106(1): 203-208.
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出版历程
  • 收稿日期:  2014-05-15
  • 修回日期:  2014-11-12

苄基芳基醚重排催化反应的研究进展

doi: 10.3969/j.issn.1006-0111.2015.06.002
  • 1. 第二军医大学药学院药物化学教研室, 上海 200433
  • 2. 总后直属供应保障局门诊部, 北京 100071
  • 收稿日期: 2014-05-15
  • 修回日期: 2014-11-12

摘要: 苄基芳基醚(BPE)的重排反应在有机化学和药物合成中具有重要作用。综述BPE在三氟乙酸、磷钨酸、环糊精、熔融锡和三溴化铝等不同催化体系中的重排反应,并探讨其可能的反应机制。

English Abstract

王重庆, 马宁宁, 杨超, 刘世豪, 朱驹, 郑灿辉. 苄基芳基醚重排催化反应的研究进展[J]. 药学实践与服务, 2015, 33(6): 486-489. doi: 10.3969/j.issn.1006-0111.2015.06.002
引用本文: 王重庆, 马宁宁, 杨超, 刘世豪, 朱驹, 郑灿辉. 苄基芳基醚重排催化反应的研究进展[J]. 药学实践与服务, 2015, 33(6): 486-489. doi: 10.3969/j.issn.1006-0111.2015.06.002
shu
WANG Chongqing, MA Ningning, YANG Chao, LIU Shihao, ZHU Ju, ZHENG Canhui. Research progress in the catalytic rearrangement reaction of benzyl phenyl ethers[J]. Journal of Pharmaceutical Practice and Service, 2015, 33(6): 486-489. doi: 10.3969/j.issn.1006-0111.2015.06.002
Citation: WANG Chongqing, MA Ningning, YANG Chao, LIU Shihao, ZHU Ju, ZHENG Canhui. Research progress in the catalytic rearrangement reaction of benzyl phenyl ethers[J]. Journal of Pharmaceutical Practice and Service, 2015, 33(6): 486-489. doi: 10.3969/j.issn.1006-0111.2015.06.002
shu

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