1-(tert-Butyl-dimethyl-silanyloxy)-6,7-bis-methylsulfanyl-1,4,4a,8a-tetrahydro-2H-isoquinoline-3,5,8-trione | 151054-71-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 1-(tert-Butyl-dimethyl-silanyloxy)-6,7-bis-methylsulfanyl-1,4,4a,8a-tetrahydro-2H-isoquinoline-3,5,8-trione
• 英文别名: 1-[tert-butyl(dimethyl)silyl]oxy-6,7-bis(methylsulfanyl)-2,4,4a,8a-tetrahydro-1H-isoquinoline-3,5,8-trione
• CAS: 151054-71-6
• 化学式: C₁₇H₂₇NO₄S₂Si
• 分子量: 401.623
• InChiKey: IEJGTOWGCDNKBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(tert-Butyl-dimethyl-silanyloxy)-6,7-bis-methylsulfanyl-1,4,4a,8a-tetrahydro-2H-isoquinoline-3,5,8-trione 在 盐酸 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以50%的产率得到2,3,5,8-tetrahydro-6,7-di-(thiomethoxy)-3,5,8-trioxoisoquinoline
  参考文献：
  名称：

  Synthesis of perfragilin B, A cytotoxic isoquinoline quinone isolated from the bryozoan Membranipora perfragilis

  摘要：

  The cytotoxic isoquinoline quinone perfragilin B (2), which was isolated from the bryozoan Membranipora perfragilis, has been synthesized. The key step involves a Diels-Alder reaction between a substituted 2-azabutadiene (4) and 2,3-bis(thiomethyl)-1,4-benzoquinone (6) to produce the isoquinoline skeleton.

  DOI：

  10.1016/s0040-4039(00)60595-6
• 作为产物：
  描述：

  2,3-di(thiomethoxy)-1,4-benzoquinone 、 甲亚胺酸,N-[1-[[(1,1-二甲基乙基)二甲基甲硅烷基]氧代]乙烯基]-,(1,1-二甲基乙基)二甲基甲硅烷基酯,(1E)- 在 甲醇 作用下， 生成 1-(tert-Butyl-dimethyl-silanyloxy)-6,7-bis-methylsulfanyl-1,4,4a,8a-tetrahydro-2H-isoquinoline-3,5,8-trione
  参考文献：
  名称：

  Synthesis of perfragilin B, A cytotoxic isoquinoline quinone isolated from the bryozoan Membranipora perfragilis

  摘要：

  The cytotoxic isoquinoline quinone perfragilin B (2), which was isolated from the bryozoan Membranipora perfragilis, has been synthesized. The key step involves a Diels-Alder reaction between a substituted 2-azabutadiene (4) and 2,3-bis(thiomethyl)-1,4-benzoquinone (6) to produce the isoquinoline skeleton.

  DOI：

  10.1016/s0040-4039(00)60595-6

文献信息

• Synthesis of perfragilin B, A cytotoxic isoquinoline quinone isolated from the bryozoan Membranipora perfragilis
  作者：Aeri Park、Francis J. Schmitz

  DOI：10.1016/s0040-4039(00)60595-6

  日期：1993.6

  The cytotoxic isoquinoline quinone perfragilin B (2), which was isolated from the bryozoan Membranipora perfragilis, has been synthesized. The key step involves a Diels-Alder reaction between a substituted 2-azabutadiene (4) and 2,3-bis(thiomethyl)-1,4-benzoquinone (6) to produce the isoquinoline skeleton.