4-[(4aR,5R,9bR)-2-ethyl-7-methyl-1,3,4,4a,5,9b-hexahydroindeno[1,2-c]pyridin-5-yl]benzoic acid | 754166-82-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 4-[(4aR,5R,9bR)-2-ethyl-7-methyl-1,3,4,4a,5,9b-hexahydroindeno[1,2-c]pyridin-5-yl]benzoic acid
• CAS: 754166-82-0
• 化学式: C₂₂H₂₅NO₂
• 分子量: 335.446
• InChiKey: GYCXUDLLLXQSNR-JBACZVJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲醇 、 4-[(4aR,5R,9bR)-2-ethyl-7-methyl-1,3,4,4a,5,9b-hexahydroindeno[1,2-c]pyridin-5-yl]benzoic acid 在 氢氧化钾 、 氯化亚砜 作用下， 生成 4-((4aR,9S,9aR)-3-Ethyl-7-methyl-2,3,4,4a,9,9a-hexahydro-1H-3-aza-fluoren-9-yl)-benzoic acid methyl ester
  参考文献：
  名称：

  Reversal of expected stereochemical outcome in the oppolzer reaction of a cyclic N-enoylsultam: Enantioselective synthesis and absolute configuration of antispermatogenic hexahydroindeno[1,2-c]pyridines

  摘要：

  p-Tolylmagnesium bromide added with high enantioselectivity to a cyclic enoylsultam (4), but the diastereofacial selectivity (determined by X-ray crystallography of the product) was opposite that reported for acyclic enoylsultams. The reaction was used in an enantioselective synthesis of antispermatogenic hexahydroindenopyridines and allowed the absolute configuration of the active enantiomer (1) to be determined. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00714-4
• 作为产物：
  描述：

  1-ethyl-3,6-dihydro-2H-pyridine-4-carboxylic acid;hydrochloride 在 正丁基锂 、 氯化亚砜 、 氢气 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 22.5h， 生成 4-[(4aR,5R,9bR)-2-ethyl-7-methyl-1,3,4,4a,5,9b-hexahydroindeno[1,2-c]pyridin-5-yl]benzoic acid
  参考文献：
  名称：

  Reversal of expected stereochemical outcome in the oppolzer reaction of a cyclic N-enoylsultam: Enantioselective synthesis and absolute configuration of antispermatogenic hexahydroindeno[1,2-c]pyridines

  摘要：

  p-Tolylmagnesium bromide added with high enantioselectivity to a cyclic enoylsultam (4), but the diastereofacial selectivity (determined by X-ray crystallography of the product) was opposite that reported for acyclic enoylsultams. The reaction was used in an enantioselective synthesis of antispermatogenic hexahydroindenopyridines and allowed the absolute configuration of the active enantiomer (1) to be determined. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00714-4

文献信息

• Reversal of expected stereochemical outcome in the oppolzer reaction of a cyclic N-enoylsultam: Enantioselective synthesis and absolute configuration of antispermatogenic hexahydroindeno[1,2-c]pyridines
  作者：Joseph M. Jump、Andrew T. McPhail、C.Edgar Cook

  DOI：10.1016/s0040-4039(97)00714-4

  日期：1997.5

  p-Tolylmagnesium bromide added with high enantioselectivity to a cyclic enoylsultam (4), but the diastereofacial selectivity (determined by X-ray crystallography of the product) was opposite that reported for acyclic enoylsultams. The reaction was used in an enantioselective synthesis of antispermatogenic hexahydroindenopyridines and allowed the absolute configuration of the active enantiomer (1) to be determined. (C) 1997 Elsevier Science Ltd.