(2R)-2-[1-(benzenesulfonyl)-3-(2-bromoethyl)indol-2-yl]-1-[(1S)-1-phenylethyl]-2,3-dihydropyridin-4-one | 411208-92-9

• 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: (2R)-2-[1-(benzenesulfonyl)-3-(2-bromoethyl)indol-2-yl]-1-[(1S)-1-phenylethyl]-2,3-dihydropyridin-4-one
• CAS: 411208-92-9
• 化学式: C₂₉H₂₇BrN₂O₃S
• 分子量: 563.515
• InChiKey: NYJZOJIFTIBJKI-RBTNQOKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  67.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R)-2-[1-(benzenesulfonyl)-3-(2-bromoethyl)indol-2-yl]-1-[(1S)-1-phenylethyl]-2,3-dihydropyridin-4-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以92%的产率得到
  参考文献：
  名称：

  Asymmetric aza-Diels–Alder reactions of indole 2-carboxaldehydes

  摘要：

  The aza-Diels-Aider reaction of substituted indole 2-carboxaldehydes with Danishefsky's diene has been investigated. The reaction proceeds with a high degree of diastercoselectivity providing highly functionalized 2-(2-piperidyl)indoles which are further elaborated into novel polycyclic heterocycles. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02070-6
• 作为产物：
  描述：

  3-(2-((tert-butyldimethylsilyl)oxy)ethyl)-1-(phenylsulfonyl)-1H-indole 在 四溴化碳 、 四丁基氟化铵 、 magnesium sulfate 、 三苯基膦 、 zinc(II) chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 14.5h， 生成 (2R)-2-[1-(benzenesulfonyl)-3-(2-bromoethyl)indol-2-yl]-1-[(1S)-1-phenylethyl]-2,3-dihydropyridin-4-one
  参考文献：
  名称：

  Asymmetric aza-Diels–Alder reactions of indole 2-carboxaldehydes

  摘要：

  The aza-Diels-Aider reaction of substituted indole 2-carboxaldehydes with Danishefsky's diene has been investigated. The reaction proceeds with a high degree of diastercoselectivity providing highly functionalized 2-(2-piperidyl)indoles which are further elaborated into novel polycyclic heterocycles. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02070-6

文献信息

• Asymmetric aza-Diels–Alder reactions of indole 2-carboxaldehydes
  作者：Jeffrey T Kuethe、Ian W Davies、Peter G Dormer、Robert A Reamer、David J Mathre、Paul J Reider

  DOI：10.1016/s0040-4039(01)02070-6

  日期：2002.1

  The aza-Diels-Aider reaction of substituted indole 2-carboxaldehydes with Danishefsky's diene has been investigated. The reaction proceeds with a high degree of diastercoselectivity providing highly functionalized 2-(2-piperidyl)indoles which are further elaborated into novel polycyclic heterocycles. (C) 2001 Elsevier Science Ltd. All rights reserved.