tert-butyl-2-(6-(benzylamino)-4,7-dihydro-4,7-dioxo-1-tosyl-1H-indol-3-yl)ethylcarbamate | 1430737-12-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl-2-(6-(benzylamino)-4,7-dihydro-4,7-dioxo-1-tosyl-1H-indol-3-yl)ethylcarbamate
• 英文别名: tert-butyl N-[2-[6-(benzylamino)-1-(4-methylphenyl)sulfonyl-4,7-dioxoindol-3-yl]ethyl]carbamate
• CAS: 1430737-12-4
• 化学式: C₂₉H₃₁N₃O₆S
• 分子量: 549.648
• InChiKey: KCGBRGKSCMSCGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  39
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  132
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl-2-(6-(benzylamino)-4,7-dihydro-4,7-dioxo-1-tosyl-1H-indol-3-yl)ethylcarbamate 、 4-benzyloxyphenylacetaldehyde diethyl acetal 在 manganese triacetate 作用下， 以 乙腈 为溶剂， 反应 40.0h， 以72%的产率得到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
  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：

  6-Methoxy-3-[2-{tert-butoxycarbonyl}amino)ethyl]-1-(p-toluenesulfonyl)indole-4,7-dione 、 苄胺 以 四氢呋喃 、 甲醇 为溶剂， 反应 20.0h， 以78%的产率得到tert-butyl-2-(6-(benzylamino)-4,7-dihydro-4,7-dioxo-1-tosyl-1H-indol-3-yl)ethylcarbamate
  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.