N_b((S)-1-methoxycarbonyl-2-methylpropyl)-tryptamine | 153077-42-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N_b((S)-1-methoxycarbonyl-2-methylpropyl)-tryptamine
• 英文别名: methyl (2S)-2-[2-(1H-indol-3-yl)ethylamino]-3-methylbutanoate
• CAS: 153077-42-0
• 化学式: C₁₆H₂₂N₂O₂
• 分子量: 274.363
• InChiKey: BJAWNHHYDHVZIB-HNNXBMFYSA-N

物化性质

• 沸点：
  428.6±30.0 °C(predicted)
• 密度：
  1.111±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  54.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N_b((S)-1-methoxycarbonyl-2-methylpropyl)-tryptamine 在 溶剂黄146 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 288.0h， 生成 2-((S)-1-methoxycarbonyl-2-methylpropyl)-1-(R)-p-nitrophenyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole
  参考文献：
  名称：

  Asymmetric steering of the Pictet-Spengler reaction by means of amino acid esters as chiral auxiliary groups

  摘要：

  N-beta-(3-Indolyl)ethyl amino acid esters and differently substituted aromatic aldehydes in the presence of acetic acid form iminium intermediates which at 6 degrees C to 40 degrees C undergo Pictet-Spengler cyclizations to give tetrahydro-beta-carbolines with diastereomer ratios up to 98.5:1.5. The chiral auxiliary group is removed from the heterocycles by employing a retro Strecker reaction as the key transformation.

  DOI：

  10.1016/s0040-4020(01)89301-7
• 作为产物：
  描述：

  3-(2-溴乙基)吲哚 、 L-缬氨酸甲酯 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 312.0h， 以57%的产率得到N_b((S)-1-methoxycarbonyl-2-methylpropyl)-tryptamine
  参考文献：
  名称：

  Asymmetric steering of the Pictet-Spengler reaction by means of amino acid esters as chiral auxiliary groups

  摘要：

  N-beta-(3-Indolyl)ethyl amino acid esters and differently substituted aromatic aldehydes in the presence of acetic acid form iminium intermediates which at 6 degrees C to 40 degrees C undergo Pictet-Spengler cyclizations to give tetrahydro-beta-carbolines with diastereomer ratios up to 98.5:1.5. The chiral auxiliary group is removed from the heterocycles by employing a retro Strecker reaction as the key transformation.

  DOI：

  10.1016/s0040-4020(01)89301-7

文献信息

• Asymmetric Pictet-Spengler reactions employing amino acid esters as mediators of selectivity
  作者：Herbert Waldmann、Gunther Schmidt、Martin Jansen、Jutta Geb

  DOI：10.1016/s0040-4039(00)73800-7

  日期：1993.9

  The Pictet-Spengler cyclization of iminium salts generated in situ from N-(β-3-indolyl)ethyl substituted amino acid esters and differently substituted aldehydes proceeds with high stereoselectivity to deliver chiral tetrahydro-β-carbolines with diastereomer ratios up to 98.5:1.5.

  由N-（β-3-吲哚基）乙基取代的氨基酸酯和不同取代的醛原位生成的亚胺盐的Pictet-Spengler环化以高立体选择性进行，以提供非对映异构体比例高达98.5：1.5的手性四氢-β-咔啉。
• Asymmetric steering of the Pictet-Spengler reaction by means of amino acid esters as chiral auxiliary groups
  作者：Herbert Waldmann、Gunther Schmidt、Martin Jansen、Jutta Geb

  DOI：10.1016/s0040-4020(01)89301-7

  日期：1994.1

  N-beta-(3-Indolyl)ethyl amino acid esters and differently substituted aromatic aldehydes in the presence of acetic acid form iminium intermediates which at 6 degrees C to 40 degrees C undergo Pictet-Spengler cyclizations to give tetrahydro-beta-carbolines with diastereomer ratios up to 98.5:1.5. The chiral auxiliary group is removed from the heterocycles by employing a retro Strecker reaction as the key transformation.