ethyl 2-(4,5-dimethylcyclohexa-1,4-dienyl)phenylcarbamate | 240132-87-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 2-(4,5-dimethylcyclohexa-1,4-dienyl)phenylcarbamate
• 英文别名: ethyl N-[2-(4,5-dimethylcyclohexa-1,4-dien-1-yl)phenyl]carbamate
• CAS: 240132-87-0
• 化学式: C₁₇H₂₁NO₂
• 分子量: 271.359
• InChiKey: SIOUTVWEKRPGDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 2-(4,5-dimethylcyclohexa-1,4-dienyl)phenylcarbamate 在 氧气 作用下， 以 二氯甲烷 为溶剂， 反应 168.0h， 以100%的产率得到ethyl (3,4-dimethylbiphenyl-2-yl)carbamate
  参考文献：
  名称：

  6-Chloro-spirocyclohexenindol-2-ones: an unusual ring transformation to ethyl 2-(cyclohexa-1,4-dienyl)phenylcarbamates

  摘要：

  The Diels-Alder cycloaddition reaction of 3-chloromethylen-2-indolones 1 with a series of dienes 2 was studied in order to synthesize spirocyclohexenindolones 3 and 4. The reaction proceeded with good diastereoselectivity and regioselectivity. Chloro spirocyclohexenindolones 3 and 4 were transformed into 2-aminobiphenyl derivatives 5 by reacting with sodium ethoxide. Starting from the indolone 1c and 2,3-dimethylbutadiene the spiro compounds 3f and 4e were obtained. On treatment with sodium ethoxide, 3f was transformed into the phenanthridone derivatives 7 and 8. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00475-5
• 作为产物：
  描述：

  ethyl (3E)-3-(chloromethylidene)-2-oxoindole-1-carboxylate 在 sodium ethanolate 、 二氯乙基铝 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 ethyl 2-(4,5-dimethylcyclohexa-1,4-dienyl)phenylcarbamate
  参考文献：
  名称：

  6-Chloro-spirocyclohexenindol-2-ones: an unusual ring transformation to ethyl 2-(cyclohexa-1,4-dienyl)phenylcarbamates

  摘要：

  The Diels-Alder cycloaddition reaction of 3-chloromethylen-2-indolones 1 with a series of dienes 2 was studied in order to synthesize spirocyclohexenindolones 3 and 4. The reaction proceeded with good diastereoselectivity and regioselectivity. Chloro spirocyclohexenindolones 3 and 4 were transformed into 2-aminobiphenyl derivatives 5 by reacting with sodium ethoxide. Starting from the indolone 1c and 2,3-dimethylbutadiene the spiro compounds 3f and 4e were obtained. On treatment with sodium ethoxide, 3f was transformed into the phenanthridone derivatives 7 and 8. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00475-5

文献信息

• 6-Chloro-spirocyclohexenindol-2-ones: an unusual ring transformation to ethyl 2-(cyclohexa-1,4-dienyl)phenylcarbamates
  作者：Egle Maria Beccalli、Francesca Clerici、Maria Luisa Gelmi

  DOI：10.1016/s0040-4020(99)00475-5

  日期：1999.7

  The Diels-Alder cycloaddition reaction of 3-chloromethylen-2-indolones 1 with a series of dienes 2 was studied in order to synthesize spirocyclohexenindolones 3 and 4. The reaction proceeded with good diastereoselectivity and regioselectivity. Chloro spirocyclohexenindolones 3 and 4 were transformed into 2-aminobiphenyl derivatives 5 by reacting with sodium ethoxide. Starting from the indolone 1c and 2,3-dimethylbutadiene the spiro compounds 3f and 4e were obtained. On treatment with sodium ethoxide, 3f was transformed into the phenanthridone derivatives 7 and 8. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.