N-{2-[7-benzyl-5-(4-benzyloxyphenyl)-1-methyl-4,8-dioxo-1,4,7,8-tetrahydropyrrolo[3,2-f]indol-3-yl]ethyl}-N-methylcarbamic acid tert-butyl ester | 1430737-16-8

• 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: N-{2-[7-benzyl-5-(4-benzyloxyphenyl)-1-methyl-4,8-dioxo-1,4,7,8-tetrahydropyrrolo[3,2-f]indol-3-yl]ethyl}-N-methylcarbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[2-[1-benzyl-7-methyl-4,8-dioxo-3-(4-phenylmethoxyphenyl)pyrrolo[3,2-f]indol-5-yl]ethyl]-N-methylcarbamate
• CAS: 1430737-16-8
• 化学式: C₃₉H₃₉N₃O₅
• 分子量: 629.756
• InChiKey: SSMYBCICHIMWDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  47
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  82.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-{2-[7-benzyl-5-(4-benzyloxyphenyl)-1-methyl-4,8-dioxo-1,4,7,8-tetrahydropyrrolo[3,2-f]indol-3-yl]ethyl}-N-methylcarbamic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Total synthesis of zyzzyanones A–D

  摘要：

  Zyzzyanones A-D is a group of biologically active marine alkaloids isolated from Australian marine sponge Zyzzya fuliginosa. They contain a unique bispyrroloquinone ring system as the core structure. The first total synthesis of all four zyzzyanones is described here. The synthesis of these alkaloids started from a previously known 6-benzylamino indole-4,7-quinone derivative and involves 6-7 steps. The key step in the synthesis involves the construction of a pyrrole ring in one step using a Mn(OAc)(3) mediated oxidative free radical cyclization reaction of a 6-benzylamino indole-4,7-quinone derivative with 4-benzyloxyphenyl acetaldehyde diethyl acetal in CH3CN. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.03.052
• 作为产物：
  描述：

  2-[7-benzyl-5-(4-benzyloxyphenyl)-4,8-dioxo-1-tosyl-1,4,7,8-tetrahydro-pyrrolo[3,2-f]indol-3-yl]ethylcarbamic acid tert-butyl ester 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 30.5h， 以46%的产率得到N-{2-[7-benzyl-5-(4-benzyloxyphenyl)-4,8-dioxo-1-tosyl-1,4,7,8-tetrahydropyrrolo[3,2-f]indol-3-yl]ethyl}-N-methylcarbamic acid tert-butyl ester
  参考文献：
  名称：

  Total synthesis of zyzzyanones A–D

  摘要：

  Zyzzyanones A-D is a group of biologically active marine alkaloids isolated from Australian marine sponge Zyzzya fuliginosa. They contain a unique bispyrroloquinone ring system as the core structure. The first total synthesis of all four zyzzyanones is described here. The synthesis of these alkaloids started from a previously known 6-benzylamino indole-4,7-quinone derivative and involves 6-7 steps. The key step in the synthesis involves the construction of a pyrrole ring in one step using a Mn(OAc)(3) mediated oxidative free radical cyclization reaction of a 6-benzylamino indole-4,7-quinone derivative with 4-benzyloxyphenyl acetaldehyde diethyl acetal in CH3CN. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.03.052

文献信息

• Total synthesis of zyzzyanones A–D
  作者：Dwayaja H. Nadkarni、Srinivasan Murugesan、Sadanandan E. Velu

  DOI：10.1016/j.tet.2013.03.052

  日期：2013.5

  Zyzzyanones A-D is a group of biologically active marine alkaloids isolated from Australian marine sponge Zyzzya fuliginosa. They contain a unique bispyrroloquinone ring system as the core structure. The first total synthesis of all four zyzzyanones is described here. The synthesis of these alkaloids started from a previously known 6-benzylamino indole-4,7-quinone derivative and involves 6-7 steps. The key step in the synthesis involves the construction of a pyrrole ring in one step using a Mn(OAc)(3) mediated oxidative free radical cyclization reaction of a 6-benzylamino indole-4,7-quinone derivative with 4-benzyloxyphenyl acetaldehyde diethyl acetal in CH3CN. (C) 2013 Elsevier Ltd. All rights reserved.