2-[5-[tert-butyl(dimethyl)silyl]oxy-1H-indol-3-yl]acetaldehyde | 1027191-66-7

• 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-[5-[tert-butyl(dimethyl)silyl]oxy-1H-indol-3-yl]acetaldehyde
• CAS: 1027191-66-7
• 化学式: C₁₆H₂₃NO₂Si
• 分子量: 289.45
• InChiKey: ZUMYKKBIYPCNEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.29
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[5-[tert-butyl(dimethyl)silyl]oxy-1H-indol-3-yl]acetaldehyde 在 potassium fluoride 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 19.0h， 生成 potassium (4R)-2-[(5-hydroxy-1H-indol-3-yl)methyl]-1,3-thiazolidine-4-carboxylate
  参考文献：
  名称：

  Chemical synthesis and structural elucidation of a new serotonin metabolite: (4R)-2-[(5′-hydroxy-1′H-indol-3′-yl)methyl]thiazolidine-4-carboxylic acid

  摘要：

  A new serotonin (5-hydroxytryptamine) metabolite, (4R)-2-[(5'-hydroxy-1'H-indol-3'-yl)methyl]thiazolidine-4-carboxylic acid (5'-HITCA),. was synthesized in 30% overall yield. The key step involved oxidation of protected 5-hydroxytryptophol using IBX followed by spontaneous cyclization with L-cysteine. The stereochemistry of condensation product thiazolidine-4-carboxylic acid was studied using NMR spectroscopy techniques. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.11.153
• 作为产物：
  描述：

  2-[5-[tert-butyl(dimethyl)silyl]oxy-1H-indol-3-yl]ethanol 在 2-碘苯甲酸 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 生成 2-[5-[tert-butyl(dimethyl)silyl]oxy-1H-indol-3-yl]acetaldehyde
  参考文献：
  名称：

  Chemical synthesis and structural elucidation of a new serotonin metabolite: (4R)-2-[(5′-hydroxy-1′H-indol-3′-yl)methyl]thiazolidine-4-carboxylic acid

  摘要：

  A new serotonin (5-hydroxytryptamine) metabolite, (4R)-2-[(5'-hydroxy-1'H-indol-3'-yl)methyl]thiazolidine-4-carboxylic acid (5'-HITCA),. was synthesized in 30% overall yield. The key step involved oxidation of protected 5-hydroxytryptophol using IBX followed by spontaneous cyclization with L-cysteine. The stereochemistry of condensation product thiazolidine-4-carboxylic acid was studied using NMR spectroscopy techniques. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.11.153