3-Chloromethyl-5-methoxy-indan-1-one | 136015-98-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 3-Chloromethyl-5-methoxy-indan-1-one
• 英文别名: 3-(Chloromethyl)-5-methoxy-2,3-dihydroinden-1-one
• CAS: 136015-98-0
• 化学式: C₁₁H₁₁ClO₂
• 分子量: 210.66
• InChiKey: CQVFMTSNLOITSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Chloromethyl-5-methoxy-indan-1-one 在 lithium diisopropyl amide 作用下， 生成 3-Methoxy-1a,6a-dihydro-1H-cyclopropa[a]inden-6-one
  参考文献：
  名称：

  Novel photochemical ring contraction of 1-naphthols promoted by aluminum halides

  摘要：

  Irradiation of 1-naphthol (1a) and its 2-alkyl and 6-methoxy derivatives 1b-d with 5 equiv of AlCl3 or AlBr3 in CH2Cl2 gave (chloromethyl)indanones 4a-d in 41-72% yields. Irradiation of 1a with AlBr3 in CH2Br2 afforded (bromomethyl)indanone 5a in 54%. 3-Methyl derivative 1e was unreactive and 4-methyl derivative 1f underwent isomerization to 1e.

  DOI：

  10.1021/jo00020a005
• 作为产物：
  描述：

  6-甲氧基-1-萘酚 在 三氯化铝 、 二氯甲烷 作用下， 反应 10.0h， 以51%的产率得到3-Chloromethyl-5-methoxy-indan-1-one
  参考文献：
  名称：

  Novel photochemical ring contraction of 1-naphthols promoted by aluminum halides

  摘要：

  Irradiation of 1-naphthol (1a) and its 2-alkyl and 6-methoxy derivatives 1b-d with 5 equiv of AlCl3 or AlBr3 in CH2Cl2 gave (chloromethyl)indanones 4a-d in 41-72% yields. Irradiation of 1a with AlBr3 in CH2Br2 afforded (bromomethyl)indanone 5a in 54%. 3-Methyl derivative 1e was unreactive and 4-methyl derivative 1f underwent isomerization to 1e.

  DOI：

  10.1021/jo00020a005

文献信息

• 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.