phenyl 1-[(E)-4-hydroxybut-2-enyl]-1,3,4,9-tetrahydropyrido[3,4-b]indole-2-carboxylate | 215025-43-7

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: phenyl 1-[(E)-4-hydroxybut-2-enyl]-1,3,4,9-tetrahydropyrido[3,4-b]indole-2-carboxylate
• CAS: 215025-43-7
• 化学式: C₂₂H₂₂N₂O₃
• 分子量: 362.428
• InChiKey: WAJLSRKCDXHWGR-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  65.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  phenyl 1-[(E)-4-hydroxybut-2-enyl]-1,3,4,9-tetrahydropyrido[3,4-b]indole-2-carboxylate 在 氢氧化钾 、 potassium carbonate 、 肼 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 74.0h， 生成 (E)-4-[2-[(Z)-2-iodobut-2-enyl]-1,3,4,9-tetrahydropyrido[3,4-b]indol-1-yl]but-2-en-1-ol
  参考文献：
  名称：

  A novel route to the geissoschizine skeleton: The influence of ligands on the diastereoselectivity of the Heck cyclization

  摘要：

  A concise, novel route to the geissoschizine skeleton has been developed. The key step involves a Heck cyclization reaction, which was found to lead to opposite diastereomers, (+/-)-8 or (+/-)-9, depending on the reaction conditions. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01591-3
• 作为产物：
  描述：

  4,9-二氢-3H-吡啶并(3,4-B)吲哚 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 phenyl 1-[(E)-4-hydroxybut-2-enyl]-1,3,4,9-tetrahydropyrido[3,4-b]indole-2-carboxylate
  参考文献：
  名称：

  A novel route to the geissoschizine skeleton: The influence of ligands on the diastereoselectivity of the Heck cyclization

  摘要：

  A concise, novel route to the geissoschizine skeleton has been developed. The key step involves a Heck cyclization reaction, which was found to lead to opposite diastereomers, (+/-)-8 or (+/-)-9, depending on the reaction conditions. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01591-3

文献信息

• A novel route to the geissoschizine skeleton: The influence of ligands on the diastereoselectivity of the Heck cyclization
  作者：Vladimir B. Birman、Viresh H. Rawal

  DOI：10.1016/s0040-4039(98)01591-3

  日期：1998.10

  A concise, novel route to the geissoschizine skeleton has been developed. The key step involves a Heck cyclization reaction, which was found to lead to opposite diastereomers, (+/-)-8 or (+/-)-9, depending on the reaction conditions. (C) 1998 Elsevier Science Ltd. All rights reserved.