rac-6-(2-(1-(tert-butyldimethylsilyl)-1H-indol-4-yl)propan-2-yl)-3-methyl-2-((trimethylsilyl)oxy)-3-vinylcyclohexanone | 1352410-70-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: rac-6-(2-(1-(tert-butyldimethylsilyl)-1H-indol-4-yl)propan-2-yl)-3-methyl-2-((trimethylsilyl)oxy)-3-vinylcyclohexanone
• 英文别名: 6-[2-[1-[Tert-butyl(dimethyl)silyl]indol-4-yl]propan-2-yl]-3-ethenyl-3-methyl-2-trimethylsilyloxycyclohexan-1-one
• CAS: 1352410-70-8
• 化学式: C₂₉H₄₇NO₂Si₂
• 分子量: 497.869
• InChiKey: LVTINBUTGOVCPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.16
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  rac-6-(2-(1-(tert-butyldimethylsilyl)-1H-indol-4-yl)propan-2-yl)-3-methyl-2-((trimethylsilyl)oxy)-3-vinylcyclohexanone 在 N-甲基吗啉 、 盐酸 、 甲醇 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 2-氯-4,6-二甲氧基-1,3,5-三嗪 、 ammonium acetate 、 sodium cyanoborohydride 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 57.0h， 生成 <6aα*-(6aα,9α,10α,10aα)>-10-formamido-2,6,6a,7,8,9,10,10a-octahydro-6,6,9-trimethyl-9-vinylnaphth<1.2.3-cd>indole
  参考文献：
  名称：

  Total Synthesis of Hapalindoles J and U

  摘要：

  The total synthesis of D,L-hapalindoles J and U has been accomplished. Hapalindole J was prepared in 11% overall yield over 11 synthetic steps and hapalindole U was prepared in 25% overall yield over 13 synthetic steps from commercially available materials. The route employs a novel silyl ether-based strategy for accessing the 6:5:6:6 ring system of the hapafindoles rapidly and in good yields.

  DOI：

  10.1021/jo202139k
• 作为产物：
  描述：

  4-溴吲哚 在 叔丁基锂 、 四氯化锡 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 4.25h， 生成 rac-6-(2-(1-(tert-butyldimethylsilyl)-1H-indol-4-yl)propan-2-yl)-3-methyl-2-((trimethylsilyl)oxy)-3-vinylcyclohexanone
  参考文献：
  名称：

  Total Synthesis of Hapalindoles J and U

  摘要：

  The total synthesis of D,L-hapalindoles J and U has been accomplished. Hapalindole J was prepared in 11% overall yield over 11 synthetic steps and hapalindole U was prepared in 25% overall yield over 13 synthetic steps from commercially available materials. The route employs a novel silyl ether-based strategy for accessing the 6:5:6:6 ring system of the hapafindoles rapidly and in good yields.

  DOI：

  10.1021/jo202139k

文献信息

• Total Synthesis of Hapalindoles J and U
  作者：Ryan J. Rafferty、Robert M. Williams

  DOI：10.1021/jo202139k

  日期：2012.1.6

  The total synthesis of D,L-hapalindoles J and U has been accomplished. Hapalindole J was prepared in 11% overall yield over 11 synthetic steps and hapalindole U was prepared in 25% overall yield over 13 synthetic steps from commercially available materials. The route employs a novel silyl ether-based strategy for accessing the 6:5:6:6 ring system of the hapafindoles rapidly and in good yields.