2-{3-[2-(5-Allyl-4-oxo-3,4-dihydro-2H-pyridin-1-yl)-ethyl]-1H-indol-2-yl}-acrylic acid methyl ester | 870197-65-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-{3-[2-(5-Allyl-4-oxo-3,4-dihydro-2H-pyridin-1-yl)-ethyl]-1H-indol-2-yl}-acrylic acid methyl ester
• 英文别名: methyl 2-[3-[2-(4-oxo-5-prop-2-enyl-2,3-dihydropyridin-1-yl)ethyl]-1H-indol-2-yl]prop-2-enoate
• CAS: 870197-65-2
• 化学式: C₂₂H₂₄N₂O₃
• 分子量: 364.444
• InChiKey: HOZUOQYGYCUDPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  62.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-{3-[2-(5-Allyl-4-oxo-3,4-dihydro-2H-pyridin-1-yl)-ethyl]-1H-indol-2-yl}-acrylic acid methyl ester 以 甲苯 为溶剂， 反应 20.0h， 以22%的产率得到18-methylene-15-oxovincadifformine
  参考文献：
  名称：

  Towards schizozygine: synthesis of 15α-hydroxystrempeliopine

  摘要：

  15 alpha-Hydroxystrempeliopine (6), a model hexacyclic base for our planned total synthesis of schizozygine (2), has been synthesized using a Zn-mediated reductive rearrangement of indolenine 14 as the key step. The structure and relative stereochemistry of 6 were assigned by a combination of COSY, NOESY, HSQC and HMBC correlations. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.09.098
• 作为产物：
  描述：

  4-[1-Chloro-meth-(E)-ylidene]-hepta-1,6-dien-3-ol 在 戴斯-马丁氧化剂 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.33h， 生成 2-{3-[2-(5-Allyl-4-oxo-3,4-dihydro-2H-pyridin-1-yl)-ethyl]-1H-indol-2-yl}-acrylic acid methyl ester
  参考文献：
  名称：

  Towards schizozygine: synthesis of 15α-hydroxystrempeliopine

  摘要：

  15 alpha-Hydroxystrempeliopine (6), a model hexacyclic base for our planned total synthesis of schizozygine (2), has been synthesized using a Zn-mediated reductive rearrangement of indolenine 14 as the key step. The structure and relative stereochemistry of 6 were assigned by a combination of COSY, NOESY, HSQC and HMBC correlations. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.09.098