(1S*,6R*)-4,5-(4'-methoxycarbonylbenzo)bicyclo<4.2.0>oct-4-en-2-one | 127703-30-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1S*,6R*)-4,5-(4'-methoxycarbonylbenzo)bicyclo<4.2.0>oct-4-en-2-one
• CAS: 127703-30-4；147730-00-5
• 化学式: C₁₄H₁₄O₃
• 分子量: 230.263
• InChiKey: ZWFPVBCUSXPKGX-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  乙烯 、 6-羟基-2-萘甲酯 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 以68%的产率得到(1S*,6R*)-4,5-(4'-methoxycarbonylbenzo)bicyclo<4.2.0>oct-4-en-2-one
  参考文献：
  名称：

  Novel photocycloaddition of 2-naphthols to ethylene in the presence of Lewis acid

  摘要：

  DOI：

  10.1016/s0040-4039(01)93339-8

文献信息

• Novel photocycloaddition of 2-naphthols to ethylene in the presence of Lewis acid
  作者：Masaki Ue、Masahiko Kinugawa、Kiyomi Kakiuchi、Yoshito Tobe、Yoshinobu Odaira

  DOI：10.1016/s0040-4039(01)93339-8

  日期：——
• Novel photochemical reactions of 1- and 2-naphthols with ethylene promoted by aluminum halides
  作者：Kiyomi Kakiuchi、Bunji Yamaguchi、Masahiko Kinugawa、Masaki Ue、Yoshito Tobe、Yoshinobu Odaira

  DOI：10.1021/jo00062a024

  日期：1993.5

  Novel photoreactions of 1- and 2-naphthols with ethylene promoted by aluminum halides are described. Irradiation of 2-naphthol (2a) with AlX3 (X = Cl, Br) and ethylene in CH2Cl2 gave the corresponding [2 + 2] cycloadduct 7a in good yields. The major side product was 2-ethyl-1-naphthol (8a). Of the Lewis acids and alkenes examined, only AlCl3 and AlBr3 effected the reaction and only ethylene gave satisfactory results, although allene can also be employed. Naphthols 2b-e having different electron-attracting substituents on C-6 afforded [2 + 2] adducts 7b-e in moderate to good yields, while the reactions of C-3-alkyl-substituted derivatives 8a and 15b were unsuccessful. By contrast, 1-naphthol (1a) and its derivatives 1b-e exhibited diverse reactivities depending on the substituent on C-2, C-3, or C-6. Namely 1a and 3-methyl derivative 1b afforded [2 + 2] cycloadducts 16a and 16b in moderate yields. On the other hand, 2-methyl and 2-propyl derivatives 1c and 1d yielded unusual products like indenones 22a and 22b and cyclopropyl ketones 23a and 23b, respectively. 6-Methoxy derivative 1e also gave indenone 30. Plausible reaction mechanisms leading to the observed products are presented.