2-(1-(tert-butyldimethylsilyl)-2-(2-methylbut-3-en-2-yl)-1H-indol-4-yl)propan-2-ol | 1448671-13-3

• 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: 2-(1-(tert-butyldimethylsilyl)-2-(2-methylbut-3-en-2-yl)-1H-indol-4-yl)propan-2-ol
• 英文别名: 2-[1-[Tert-butyl(dimethyl)silyl]-2-(2-methylbut-3-en-2-yl)indol-4-yl]propan-2-ol；2-[1-[tert-butyl(dimethyl)silyl]-2-(2-methylbut-3-en-2-yl)indol-4-yl]propan-2-ol
• CAS: 1448671-13-3
• 化学式: C₂₂H₃₅NOSi
• 分子量: 357.611
• InChiKey: CWYTXCHDWYBOCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.19
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  25.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(1-(tert-butyldimethylsilyl)-2-(2-methylbut-3-en-2-yl)-1H-indol-4-yl)propan-2-ol 在 盐酸 、 四氯化锡 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 53.25h， 生成 racemic-(8R,9S)-8-hydroxy-6,6,9-trimethyl-1-(2-methylbut-3-en-2-yl)-9-vinyl-6,7,8,9-tetrahydronaphtho[1,2,3-cd]indol-10(2H)-one
  参考文献：
  名称：

  Formal Synthesis of Hapalindole O and Synthetic Efforts towards Hapalindole K and Ambiguine A

  摘要：

  The formal synthesis of D,L-hapalindole O has been accomplished intercepting Natsume's total synthesis route. The intercepted substrate was synthesized in an overall 36% yield over ten-synthetic steps compared to Natsume's overall 1% yield over eighteen-synthetic steps. In addition, advanced substrates for the continuing progress towards hapalindole K and ambiguine A has been synthesized. All routes described herein employ a silyl ether-based strategy accessing the functionalized 6:5:6:6 ring system, that has previously been used in our laboratory to access the total synthesis of D,L-hapalindoles J and U.

  DOI：

  10.3987/com-12-s(n)3
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 叔丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 4.0h， 生成 2-(1-(tert-butyldimethylsilyl)-2-(2-methylbut-3-en-2-yl)-1H-indol-4-yl)propan-2-ol
  参考文献：
  名称：

  Formal Synthesis of Hapalindole O and Synthetic Efforts towards Hapalindole K and Ambiguine A

  摘要：

  The formal synthesis of D,L-hapalindole O has been accomplished intercepting Natsume's total synthesis route. The intercepted substrate was synthesized in an overall 36% yield over ten-synthetic steps compared to Natsume's overall 1% yield over eighteen-synthetic steps. In addition, advanced substrates for the continuing progress towards hapalindole K and ambiguine A has been synthesized. All routes described herein employ a silyl ether-based strategy accessing the functionalized 6:5:6:6 ring system, that has previously been used in our laboratory to access the total synthesis of D,L-hapalindoles J and U.

  DOI：

  10.3987/com-12-s(n)3

文献信息

• Formal Synthesis of Hapalindole O and Synthetic Efforts towards Hapalindole K and Ambiguine A
  作者：Robert M. Williams、Ryan J. Rafferty

  DOI：10.3987/com-12-s(n)3

  日期：——

  The formal synthesis of D,L-hapalindole O has been accomplished intercepting Natsume's total synthesis route. The intercepted substrate was synthesized in an overall 36% yield over ten-synthetic steps compared to Natsume's overall 1% yield over eighteen-synthetic steps. In addition, advanced substrates for the continuing progress towards hapalindole K and ambiguine A has been synthesized. All routes described herein employ a silyl ether-based strategy accessing the functionalized 6:5:6:6 ring system, that has previously been used in our laboratory to access the total synthesis of D,L-hapalindoles J and U.