2-azido-(4-isopropenyl-cyclohex-1-enylmethyl)-1H-indole-3-carbaldehyde | 329765-59-5

• 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: 2-azido-(4-isopropenyl-cyclohex-1-enylmethyl)-1H-indole-3-carbaldehyde
• CAS: 329765-59-5
• 化学式: C₁₉H₂₀N₄O
• 分子量: 320.394
• InChiKey: VLCCERMOLACSQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  70.76
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-azido-(4-isopropenyl-cyclohex-1-enylmethyl)-1H-indole-3-carbaldehyde 在 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 13.5h， 生成 [2-amino-1-(4-isopropenyl-cyclohex-1-enylmethyl)-1H-indole-3-yl]morpholin-4-yl-methanone
  参考文献：
  名称：

  2-Amidinylindole-3-carbaldehydes: Versatile Synthons for the Preparation of α-Carboline Derivatives

  摘要：

  The 2-amidinylindole-3-carbaldehydes 1 are the key starting materials for the preparation of three classes of carbolines 2, 6 and 7 in which the pyridine ring is characterised by a different substitution patterns. The carbolines 2 which are functionalized with an amino group in position 2, were obtained directly by heating 1 in presence of SiO2. The condensation of amidines 1 with arylmethylketones afforded unsaturated ketones 5 which on heating were transformed into 2, 9-dialkyl-3-aroyl-9H-pyrido[2,3-b]indoles 7. Instead, prolonged reaction of amidines 1 with arylmethylketones in t-BuOH/t-BuOK gave 2-aryl-9H-pyrido[2,3-b]indoles 6. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00950-9
• 作为产物：
  描述：

  2-溴-1H-吲哚-3-甲醛 在 sodium azide 、 sodium hydride 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 53.5h， 生成 2-azido-(4-isopropenyl-cyclohex-1-enylmethyl)-1H-indole-3-carbaldehyde
  参考文献：
  名称：

  2-Amidinylindole-3-carbaldehydes: Versatile Synthons for the Preparation of α-Carboline Derivatives

  摘要：

  The 2-amidinylindole-3-carbaldehydes 1 are the key starting materials for the preparation of three classes of carbolines 2, 6 and 7 in which the pyridine ring is characterised by a different substitution patterns. The carbolines 2 which are functionalized with an amino group in position 2, were obtained directly by heating 1 in presence of SiO2. The condensation of amidines 1 with arylmethylketones afforded unsaturated ketones 5 which on heating were transformed into 2, 9-dialkyl-3-aroyl-9H-pyrido[2,3-b]indoles 7. Instead, prolonged reaction of amidines 1 with arylmethylketones in t-BuOH/t-BuOK gave 2-aryl-9H-pyrido[2,3-b]indoles 6. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00950-9