(S)-methyl 5-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine-5-carboxylate | 1347702-90-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: (S)-methyl 5-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine-5-carboxylate
• 英文别名: methyl (5S)-5-methyl-2-oxo-3,4-dihydro-1H-1-benzazepine-5-carboxylate
• CAS: 1347702-90-2
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: KYPMPYHXMBUAFZ-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-methyl 5-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine-5-carboxylate 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 lithium aluminium tetrahydride 、 叠氮磷酸二苯酯 、 水 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 74.5h， 生成 (3AS,8AR)-5-甲氧基-1,3A,8-三甲基-1,2,3,3A,8,8A-六氢吡咯并[2,3-B]吲哚
  参考文献：
  名称：

  Ethylene in Organic Synthesis: A New Route to Anticholenergic Pyrrolidinoindolines, and Other Molecules with All Carbon-Quaternary Centers via Asymmetric Hydrovinylation

  摘要：

  The asymmetric hydrovinylation (1 mol % Ni-cat., 1 atm, ethylene, >98% ee) products from 1-methylenetetralines are readily converted into 3, 3-disubstituted oxindoles and subsequently to pyrrolidinoindolines. These hydrovinylation products are also useful for the syntheses of enantiopure benzomorphans.

  DOI：

  10.1021/ol203052y
• 作为产物：
  描述：

  (S)-1-methyl-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid 在 chromium(VI) oxide 、 sodium azide 、 potassium carbonate 作用下， 以 乙酸酐 、 溶剂黄146 、 丙酮 为溶剂， 反应 41.17h， 生成 (S)-methyl 5-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine-5-carboxylate
  参考文献：
  名称：

  Ethylene in Organic Synthesis: A New Route to Anticholenergic Pyrrolidinoindolines, and Other Molecules with All Carbon-Quaternary Centers via Asymmetric Hydrovinylation

  摘要：

  The asymmetric hydrovinylation (1 mol % Ni-cat., 1 atm, ethylene, >98% ee) products from 1-methylenetetralines are readily converted into 3, 3-disubstituted oxindoles and subsequently to pyrrolidinoindolines. These hydrovinylation products are also useful for the syntheses of enantiopure benzomorphans.

  DOI：

  10.1021/ol203052y

文献信息

• Ethylene in Organic Synthesis: A New Route to Anticholenergic Pyrrolidinoindolines, and Other Molecules with All Carbon-Quaternary Centers via Asymmetric Hydrovinylation
  作者：Hwan Jung Lim、T. V. RajanBabu

  DOI：10.1021/ol203052y

  日期：2011.12.16

  The asymmetric hydrovinylation (1 mol % Ni-cat., 1 atm, ethylene, >98% ee) products from 1-methylenetetralines are readily converted into 3, 3-disubstituted oxindoles and subsequently to pyrrolidinoindolines. These hydrovinylation products are also useful for the syntheses of enantiopure benzomorphans.