3-{2-[[2-(2-Azido-phenyl)-2-diazo-acetyl]-(1-methyl-1-phenyl-ethyl)-amino]-ethyl}-indole-1-carboxylic acid tert-butyl ester | 890137-00-5

• 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: 3-{2-[[2-(2-Azido-phenyl)-2-diazo-acetyl]-(1-methyl-1-phenyl-ethyl)-amino]-ethyl}-indole-1-carboxylic acid tert-butyl ester
• 英文别名: [1-(6-Diazonioiminocyclohexa-2,4-dien-1-ylidene)-2-[2-[1-[(2-methylpropan-2-yl)oxycarbonyl]indol-3-yl]ethyl-(2-phenylpropan-2-yl)amino]-2-oxoethyl]iminoazanide；[1-(6-diazonioiminocyclohexa-2,4-dien-1-ylidene)-2-[2-[1-[(2-methylpropan-2-yl)oxycarbonyl]indol-3-yl]ethyl-(2-phenylpropan-2-yl)amino]-2-oxoethyl]iminoazanide
• CAS: 890137-00-5
• 化学式: C₃₂H₃₃N₇O₃
• 分子量: 563.659
• InChiKey: VAYRBPHBNFPIKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  42
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-{2-[[2-(2-Azido-phenyl)-2-diazo-acetyl]-(1-methyl-1-phenyl-ethyl)-amino]-ethyl}-indole-1-carboxylic acid tert-butyl ester 在 三氟甲烷磺酸亚铜(I)苯联合体 (2:1) 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以85%的产率得到
  参考文献：
  名称：

  Biomimetic Approach to Perophoramidine and Communesin via an Intramolecular Cyclopropanation Reaction

  摘要：

  Starting from tryptamine 4 and isatin 5, a biomimetic approach to the pentacyclic substructure 1 of perophoramidine and communesin was developed. The key steps were to create a stable three/six bicyclic system 2 on the 2,3-double bond of an indole derivative 3 by an intramolecular cyclopropanation, followed by ring opening of the resulting cyclopropane ring with the in situ generated amine group of an aniline.

  DOI：

  10.1021/ol0607138
• 作为产物：
  描述：

  3-(2-溴乙基)吲哚 在 4-二甲氨基吡啶 、 sodium hydride 、 potassium carbonate 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.5h， 生成 3-{2-[[2-(2-Azido-phenyl)-2-diazo-acetyl]-(1-methyl-1-phenyl-ethyl)-amino]-ethyl}-indole-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Biomimetic Approach to Perophoramidine and Communesin via an Intramolecular Cyclopropanation Reaction

  摘要：

  Starting from tryptamine 4 and isatin 5, a biomimetic approach to the pentacyclic substructure 1 of perophoramidine and communesin was developed. The key steps were to create a stable three/six bicyclic system 2 on the 2,3-double bond of an indole derivative 3 by an intramolecular cyclopropanation, followed by ring opening of the resulting cyclopropane ring with the in situ generated amine group of an aniline.

  DOI：

  10.1021/ol0607138

文献信息

• Biomimetic Approach to Perophoramidine and Communesin via an Intramolecular Cyclopropanation Reaction
  作者：Jun Yang、Hao Song、Xue Xiao、Jue Wang、Yong Qin

  DOI：10.1021/ol0607138

  日期：2006.5.1

  Starting from tryptamine 4 and isatin 5, a biomimetic approach to the pentacyclic substructure 1 of perophoramidine and communesin was developed. The key steps were to create a stable three/six bicyclic system 2 on the 2,3-double bond of an indole derivative 3 by an intramolecular cyclopropanation, followed by ring opening of the resulting cyclopropane ring with the in situ generated amine group of an aniline.