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 | 142260-73-9

• 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: 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
• CAS: 142260-73-9；142392-99-2
• 化学式: C₂₂H₂₇N₃O₄
• 分子量: 397.474
• InChiKey: SXPPBKBPNADXJM-KSZLIROESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.71
• 重原子数：
  29.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  74.87
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  2,2-dimethyl-5-(ethoxycarbonyl)-4,5,6,11b-tetrahydroisoxazolidino<2,3-a>-β-carboline 在 palladium on activated charcoal titanium(IV) isopropylate 、 草酰氯 、 氢气 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 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
  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 verruculogen TR-2 featuring the mild formation of a dihydro-.beta.-carboline as an intermediate
  作者：Pedro H. H. Hermkens、Ralf Plate、Chris G. Kruse、Hans W. Scheeren、Harry C. J. Ottenheijm

  DOI：10.1021/jo00040a030

  日期：1992.7

  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.