6,7-Dibromo-N-<(6-bromo-indol-3-yl)cyanomethyl>-4-methoxy-N-methyl-α-oxoindole-3-acetamide | 158920-15-1

• 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: 6,7-Dibromo-N-<(6-bromo-indol-3-yl)cyanomethyl>-4-methoxy-N-methyl-α-oxoindole-3-acetamide
• 英文别名: N-[(6-bromo-1H-indol-3-yl)-cyanomethyl]-2-(6,7-dibromo-4-methoxy-1H-indol-3-yl)-N-methyl-2-oxoacetamide
• CAS: 158920-15-1
• 化学式: C₂₂H₁₅Br₃N₄O₃
• 分子量: 623.098
• InChiKey: YWCHCLHAZLOEGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,7-Dibromo-N-<(6-bromo-indol-3-yl)cyanomethyl>-4-methoxy-N-methyl-α-oxoindole-3-acetamide 在 四丁基硫酸氢铵 sodium hydroxide 、 双氧水 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以92%的产率得到N-<2-Amino-1-(6-bromoindol-3-yl)-2-oxoethyl>-6,7-dibromo-4-methoxy-N-methyl-α-oxoindole-3-acetamide
  参考文献：
  名称：

  Total Synthesis of (.+-.)-Dragmacidin: A Cytotoxic Bis(indole)alkaloid of Marine Origin

  摘要：

  The total synthesis of the cytotoxic marine alkaloid, (+/-)-dragmacidin, trans-6,7-dibromo-3-[5-(6-bromo-1H-indol-3-yl)-4-methyl-2-piperazinyl]-1H-indol-4-ol, is described. The synthesis proceeds through the condensation of (6-bromoindol-3-yl)-alpha-(methylamino)acetonitrile with (6,7-dibromo-4-methoxyindol-3-yl)-alpha-oxoacetyl chloride. The product of this condensation was converted in two steps to an intermediate containing the central diketopiperazine ring which after reduction and deprotection gave the racemic natural product along with its cis isomer. An efficient preparation of 6,7-dibromo-4-methoxyindole is also presented.

  DOI：

  10.1021/jo00101a051
• 作为产物：
  描述：

  6-溴吲哚 在 三乙胺 、 三氯氧磷 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 6,7-Dibromo-N-<(6-bromo-indol-3-yl)cyanomethyl>-4-methoxy-N-methyl-α-oxoindole-3-acetamide
  参考文献：
  名称：

  Total Synthesis of (.+-.)-Dragmacidin: A Cytotoxic Bis(indole)alkaloid of Marine Origin

  摘要：

  The total synthesis of the cytotoxic marine alkaloid, (+/-)-dragmacidin, trans-6,7-dibromo-3-[5-(6-bromo-1H-indol-3-yl)-4-methyl-2-piperazinyl]-1H-indol-4-ol, is described. The synthesis proceeds through the condensation of (6-bromoindol-3-yl)-alpha-(methylamino)acetonitrile with (6,7-dibromo-4-methoxyindol-3-yl)-alpha-oxoacetyl chloride. The product of this condensation was converted in two steps to an intermediate containing the central diketopiperazine ring which after reduction and deprotection gave the racemic natural product along with its cis isomer. An efficient preparation of 6,7-dibromo-4-methoxyindole is also presented.

  DOI：

  10.1021/jo00101a051

文献信息

• Total Synthesis of (.+-.)-Dragmacidin: A Cytotoxic Bis(indole)alkaloid of Marine Origin
  作者：Biao Jiang、Joanne M. Smallheer、Carol Amaral-Ly、Mark A. Wuonola

  DOI：10.1021/jo00101a051

  日期：1994.11

  The total synthesis of the cytotoxic marine alkaloid, (+/-)-dragmacidin, trans-6,7-dibromo-3-[5-(6-bromo-1H-indol-3-yl)-4-methyl-2-piperazinyl]-1H-indol-4-ol, is described. The synthesis proceeds through the condensation of (6-bromoindol-3-yl)-alpha-(methylamino)acetonitrile with (6,7-dibromo-4-methoxyindol-3-yl)-alpha-oxoacetyl chloride. The product of this condensation was converted in two steps to an intermediate containing the central diketopiperazine ring which after reduction and deprotection gave the racemic natural product along with its cis isomer. An efficient preparation of 6,7-dibromo-4-methoxyindole is also presented.