3,4-Dibromo-1-triisopropylsilanyl-1H-indole | 406170-05-6

• 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: 3,4-Dibromo-1-triisopropylsilanyl-1H-indole
• 英文别名: (3,4-Dibromoindol-1-yl)-tri(propan-2-yl)silane
• CAS: 406170-05-6
• 化学式: C₁₇H₂₅Br₂NSi
• 分子量: 431.286
• InChiKey: ALLBQPNNULHCIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.19
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3,4-Dibromo-1-triisopropylsilanyl-1H-indole 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 生成 3,4-dibromo-1H-indole
  参考文献：
  名称：

  Rapid Route to 3,4-Substituted Indoles via a Directed Ortho Metalation−Retro-Mannich Sequence

  摘要：

  [GRAPHICS]In the presence of NXS (X = Br, I, Cl), gramine derivatives 1, derived by combined directed ortho metalation (DoM)-cross-coupling sequences, rapidly undergo retro-Mannich fragmentation (2) to afford 3-halo indoles 3 in 37-88% yields. A conceptually new methodology to diverse 3,4-substituted indoles (10, 11, 13) is thereby introduced.

  DOI：

  10.1021/ol017310m
• 作为产物：
  描述：

  1-(triisopropylsilyl)gramine 在 N-溴代丁二酰亚胺(NBS) 、 叔丁基锂 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 正戊烷 为溶剂， 反应 1.03h， 生成 3,4-Dibromo-1-triisopropylsilanyl-1H-indole
  参考文献：
  名称：

  Rapid Route to 3,4-Substituted Indoles via a Directed Ortho Metalation−Retro-Mannich Sequence

  摘要：

  [GRAPHICS]In the presence of NXS (X = Br, I, Cl), gramine derivatives 1, derived by combined directed ortho metalation (DoM)-cross-coupling sequences, rapidly undergo retro-Mannich fragmentation (2) to afford 3-halo indoles 3 in 37-88% yields. A conceptually new methodology to diverse 3,4-substituted indoles (10, 11, 13) is thereby introduced.

  DOI：

  10.1021/ol017310m

文献信息

• Rapid Route to 3,4-Substituted Indoles via a Directed Ortho Metalation−Retro-Mannich Sequence
  作者：Brian Chauder、Andrew Larkin、Victor Snieckus

  DOI：10.1021/ol017310m

  日期：2002.3.1

  [GRAPHICS]In the presence of NXS (X = Br, I, Cl), gramine derivatives 1, derived by combined directed ortho metalation (DoM)-cross-coupling sequences, rapidly undergo retro-Mannich fragmentation (2) to afford 3-halo indoles 3 in 37-88% yields. A conceptually new methodology to diverse 3,4-substituted indoles (10, 11, 13) is thereby introduced.