2-(7-Allyl-6,7,8,9-tetrahydro-5H-1,3-dioxa-7,9-diaza-cyclopenta[b]fluoren-8-ylmethyl)-1,1-dioxo-2,5-dihydro-1H-1λ⁶-thiophene-3-carboxylic acid methyl ester | 189681-68-3

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-(7-Allyl-6,7,8,9-tetrahydro-5H-1,3-dioxa-7,9-diaza-cyclopenta[b]fluoren-8-ylmethyl)-1,1-dioxo-2,5-dihydro-1H-1λ⁶-thiophene-3-carboxylic acid methyl ester
• CAS: 189681-68-3
• 化学式: C₂₂H₂₄N₂O₆S
• 分子量: 444.508
• InChiKey: OUCBNFVBPGXKOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.27
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  97.93
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-(7-Allyl-6,7,8,9-tetrahydro-5H-1,3-dioxa-7,9-diaza-cyclopenta[b]fluoren-8-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54%的产率得到methyl (2S,4S,9R)-18,20-dioxa-11,24-diazahexacyclo[12.10.0.02,11.04,9.015,23.017,21]tetracosa-1(14),5,15,17(21),22-pentaene-5-carboxylate
  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：

  N-Allyl-2-(5H-[1,3]dioxolo[4,5-f]indol-7-yl)-2-oxo-acetamide 在 lithium aluminium tetrahydride 、 溶剂黄146 作用下， 以 乙醚 为溶剂， 生成 2-(7-Allyl-6,7,8,9-tetrahydro-5H-1,3-dioxa-7,9-diaza-cyclopenta[b]fluoren-8-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