8-(16-hydroxy-16-methylpropyl)-7,8,14,14a-tetrahydro-pyrrolidino-<1,2-c>piperazino-<1',6'-2,3>-β-carboline-(5aHα,8Hβ,14aHα)-1,6-dione | 106292-67-5

• 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: 8-(16-hydroxy-16-methylpropyl)-7,8,14,14a-tetrahydro-pyrrolidino-<1,2-c>piperazino-<1',6'-2,3>-β-carboline-(5aHα,8Hβ,14aHα)-1,6-dione
• 英文别名: 8-(2'-hydroxy-2'-methylpropyl)-4,5,5a,8,14,14a-hexahydro-3H-pyrrolo<1',2':4,5>pyrazino<1,2-b>-β-carboline-(5aHα,8Hβ,14aHα)-1,6-dione；8-(2'-hydroxy-2'-methylpropyl)-4,5,5a,8,14,14a-hexahydro-3H-pyrrolo[1',2':4,5]pyrazino[1,2-b]-β-carboline-(5aHα,8Hβ,14aHα)-1,6-dione；(1S,12R,15S)-12-(2-hydroxy-2-methylpropyl)-10,13,19-triazapentacyclo[11.7.0.03,11.04,9.015,19]icosa-3(11),4,6,8-tetraene-14,20-dione
• CAS: 106292-67-5
• 化学式: C₂₁H₂₅N₃O₃
• 分子量: 367.448
• InChiKey: RFFYLCRCNILFBP-YESZJQIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  76.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-(16-hydroxy-16-methylpropyl)-7,8,14,14a-tetrahydro-pyrrolidino-<1,2-c>piperazino-<1',6'-2,3>-β-carboline-(5aHα,8Hβ,14aHα)-1,6-dione 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以95%的产率得到(15S)-12-(2-hydroxy-2-methylpropyl)-10,13,19-triazapentacyclo[11.7.0.03,11.04,9.015,19]icosa-1,3,5,7,9,11-hexaene-14,20-dione
  参考文献：
  名称：

  Stereoselective synthesis of verruculogen TR-2 featuring the mild formation of a dihydro-.beta.-carboline as an intermediate

  摘要：

  Reaction of indolyldiketopiperazine 5 with 2,3,4,5,6,6-hexachlorocyclohexadien-1-one (25) in dichloromethane/methanol provided the methoxyindolenine 29, which in the presence of TFA rearranged to the dehydrodiketopiperazine 6. This compound was elaborated to verruculogen TR-2 (2) employing osmium tetroxide oxidation.

  DOI：

  10.1021/jo00040a030
• 作为产物：
  描述：

  methyl (2S)-1-[(2S,7R)-4,4-dimethyl-5-oxa-6,16-diazatetracyclo[7.7.0.02,6.010,15]hexadeca-1(9),10,12,14-tetraene-7-carbonyl]pyrrolidine-2-carboxylate 在 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 锌 作用下， 生成 8-(16-hydroxy-16-methylpropyl)-7,8,14,14a-tetrahydro-pyrrolidino-<1,2-c>piperazino-<1',6'-2,3>-β-carboline-(5aHα,8Hβ,14aHα)-1,6-dione
  参考文献：
  名称：

  Stereoselective synthesis of verruculogen TR-2 featuring the mild formation of a dihydro-.beta.-carboline as an intermediate

  摘要：

  Reaction of indolyldiketopiperazine 5 with 2,3,4,5,6,6-hexachlorocyclohexadien-1-one (25) in dichloromethane/methanol provided the methoxyindolenine 29, which in the presence of TFA rearranged to the dehydrodiketopiperazine 6. This compound was elaborated to verruculogen TR-2 (2) employing osmium tetroxide oxidation.

  DOI：

  10.1021/jo00040a030

文献信息

• Stereoselective synthesis of desmethoxy-(+)-verruculogen TR-2
  作者：Steven A. Boyd、Wayne J. Thompson

  DOI：10.1021/jo00385a025

  日期：1987.5
• Application of an isoxazolidine in a stereoselective approach to the fumitremorgin series
  作者：Ralf Plate、Pedro H. H. Hermkens、Helmut Behm、Harry C. J. Ottenheijm

  DOI：10.1021/jo00380a015

  日期：1987.2