2-(2-Allyl-7-methoxy-2,3,4,9-tetrahydro-1H-β-carbolin-1-ylmethyl)-1,1-dioxo-2,5-dihydro-1H-1λ⁶-thiophene-3-carboxylic acid methyl ester | 189681-67-2

• 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: 2-(2-Allyl-7-methoxy-2,3,4,9-tetrahydro-1H-β-carbolin-1-ylmethyl)-1,1-dioxo-2,5-dihydro-1H-1λ⁶-thiophene-3-carboxylic acid methyl ester
• 英文别名: Methyl 2-[(7-methoxy-2-prop-2-enyl-1,3,4,9-tetrahydropyrido[3,4-b]indol-1-yl)methyl]-1,1-dioxo-2,5-dihydrothiophene-3-carboxylate；methyl 2-[(7-methoxy-2-prop-2-enyl-1,3,4,9-tetrahydropyrido[3,4-b]indol-1-yl)methyl]-1,1-dioxo-2,5-dihydrothiophene-3-carboxylate
• CAS: 189681-67-2
• 化学式: C₂₂H₂₆N₂O₅S
• 分子量: 430.525
• InChiKey: NSBBEMZJLGGOBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  97.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(2-Allyl-7-methoxy-2,3,4,9-tetrahydro-1H-β-carbolin-1-ylmethyl)-1,1-dioxo-2,5-dihydro-1H-1λ⁶-thiophene-3-carboxylic acid methyl ester 以 甲苯 为溶剂， 反应 18.0h， 以47%的产率得到(4aR,13bS,14aS)-11-Methoxy-3,4,4a,5,7,8,13,13b,14,14a-decahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester
  参考文献：
  名称：

  A One-Pot Tandem Pictet-Spengler-Diels-Alder Synthesis of Apoyohimbines from 3-Carbomethoxy-2-(formylmethyl)-3-sulfolene

  摘要：

  Pictet-Spengler reactions were carried out between 3-carbomethoxy-2-(formylmethyl)-3-sulfolene and tryptamines. Without isolation, the products were converted with complete stereoselectivity into apoyohimbine derivatives, via sulfur dioxide extrusion followed by intramolecular Diels-Alder cyclisation. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00547-9
• 作为产物：
  描述：

  (6-methoxy-1H-indol-3-yl)(oxo)acetyl chloride 在 lithium aluminium tetrahydride 、 溶剂黄146 、 三乙胺 作用下， 以 乙醚 为溶剂， 生成 2-(2-Allyl-7-methoxy-2,3,4,9-tetrahydro-1H-β-carbolin-1-ylmethyl)-1,1-dioxo-2,5-dihydro-1H-1λ⁶-thiophene-3-carboxylic acid methyl ester
  参考文献：
  名称：

  A One-Pot Tandem Pictet-Spengler-Diels-Alder Synthesis of Apoyohimbines from 3-Carbomethoxy-2-(formylmethyl)-3-sulfolene

  摘要：

  Pictet-Spengler reactions were carried out between 3-carbomethoxy-2-(formylmethyl)-3-sulfolene and tryptamines. Without isolation, the products were converted with complete stereoselectivity into apoyohimbine derivatives, via sulfur dioxide extrusion followed by intramolecular Diels-Alder cyclisation. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00547-9