ethyl 1,9-diallyl-1,2,3,4-tetrahydro-β-carbolinecarboxylate | 1448448-70-1

• 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: ethyl 1,9-diallyl-1,2,3,4-tetrahydro-β-carbolinecarboxylate
• CAS: 1448448-70-1
• 化学式: C₂₀H₂₄N₂O₂
• 分子量: 324.423
• InChiKey: LNSRNAGMUMWOKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.46
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  34.47
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl 1,9-diallyl-1,2,3,4-tetrahydro-β-carbolinecarboxylate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 、 mineral oil 为溶剂， 反应 3.5h， 生成 (±)-debromoarborescidine
  参考文献：
  名称：

  Indirect N-vinylation of indoles via isomerisation of N-allyl derivatives: synthesis of (±)-debromoarborescidine B

  摘要：

  Double bond migration in N-allylindoles has been investigated as a method to access N-vinyl derivatives of this heterocycle. The optimal reaction conditions employed t-BuOK or NaH in DMSO as the solvent at room temperature to afford the products in yields ranging from 51 to 99%. Although in some cases a high degree of stereoselectivity was observed, preferential formation of either the Z- or E-isomer was not predictable. The developed methodology was employed in the synthesis of (+/-)-debromoarborescidine B. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.06.069
• 作为产物：
  描述：

  4,9-二氢-3H-吡啶并(3,4-B)吲哚 在 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 5.0h， 生成 ethyl 1,9-diallyl-1,2,3,4-tetrahydro-β-carbolinecarboxylate
  参考文献：
  名称：

  Indirect N-vinylation of indoles via isomerisation of N-allyl derivatives: synthesis of (±)-debromoarborescidine B

  摘要：

  Double bond migration in N-allylindoles has been investigated as a method to access N-vinyl derivatives of this heterocycle. The optimal reaction conditions employed t-BuOK or NaH in DMSO as the solvent at room temperature to afford the products in yields ranging from 51 to 99%. Although in some cases a high degree of stereoselectivity was observed, preferential formation of either the Z- or E-isomer was not predictable. The developed methodology was employed in the synthesis of (+/-)-debromoarborescidine B. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.06.069