4-(2-hydroxy-2-propyl)-N-TBS-indole | 1352410-69-5

• 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: 4-(2-hydroxy-2-propyl)-N-TBS-indole
• 英文别名: 2-[1-[Tert-butyl(dimethyl)silyl]indol-4-yl]propan-2-ol
• CAS: 1352410-69-5
• 化学式: C₁₇H₂₇NOSi
• 分子量: 289.493
• InChiKey: FYQNGSUESCWCTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.72
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  (5-Ethenyl-5-methyl-6-trimethylsilyloxycyclohexen-1-yl)oxy-trimethylsilane 、 4-(2-hydroxy-2-propyl)-N-TBS-indole 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以92%的产率得到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
• 作为产物：
  描述：

  4-溴吲哚 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 4-(2-hydroxy-2-propyl)-N-TBS-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

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.
• 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.