4-formyl-1-(triisopropyl)gramine | 146886-62-6

• 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: 4-formyl-1-(triisopropyl)gramine
• 英文别名: 3-[(Dimethylamino)methyl]-1-tri(propan-2-yl)silylindole-4-carbaldehyde
• CAS: 146886-62-6
• 化学式: C₂₁H₃₄N₂OSi
• 分子量: 358.599
• InChiKey: CJAAUVSJFWKFPO-UHFFFAOYSA-N

物化性质

• 沸点：
  394.4±40.0 °C(predicted)
• 密度：
  0.98±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.54
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-formyl-1-(triisopropyl)gramine 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-[(二甲氨基)甲基]-1H-吲哚-4-甲醛
  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：

  三异丙基氯硅烷 在 正丁基锂 、 叔丁基锂 作用下， 反应 7.25h， 生成 4-formyl-1-(triisopropyl)gramine
  参考文献：
  名称：

  Directed Lithiation of 1-Triisopropylsilylgramine. A Short Access to 3,4-Disubstituted Indoles

  摘要：

  1-Triisopropylsilylgramine was lithiated regioselectively at C-4 by treatment with t-BuLi in ether at 0-degrees-C for 1 h. The lithiated species was trapped with a variety of electrophiles to furnish 4-functionalized gramine derivatives in good yields. Replacement of the triisopropylsilyl protecting group by a methyl group resulted in C-2 selective lithiation under the similar reaction conditions.

  DOI：

  10.3987/com-92-6185

文献信息

• Generation of Aza-<i>o</i><i>rtho</i>-xylylenes via Ring Opening of 2-(2-Acylaminophenyl)aziridines:  Application in the Construction of the Communesin Ring System
  作者：Seth L. Crawley、Raymond L. Funk

  DOI：10.1021/ol061461d

  日期：2006.8.1

  A new protocol for generating aza-ortho-xylylenes via acid-catalyzed or fluoride-promoted ring opening of 2-(2-acylaminophenyl) aziridines is described. This methodology has been exploited in the rapid construction of a hexacyclic substructure of communesin B.