2-((S)-1-methoxycarbonyl-2-methylpropyl)-1-(S)-p-nitrophenyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole | 153077-47-5

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: 2-((S)-1-methoxycarbonyl-2-methylpropyl)-1-(S)-p-nitrophenyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole
• CAS: 153077-47-5
• 化学式: C₂₃H₂₅N₃O₄
• 分子量: 407.469
• InChiKey: QSUIEGAMWMFHOB-VXKWHMMOSA-N

物化性质

• 沸点：
  565.7±50.0 °C(predicted)
• 密度：
  1.268±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.22
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  88.47
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-((S)-1-methoxycarbonyl-2-methylpropyl)-1-(S)-p-nitrophenyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole 在 溶剂黄146 作用下， 以 苯 为溶剂， 反应 72.0h， 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 在 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 528.0h， 生成 2-((S)-1-methoxycarbonyl-2-methylpropyl)-1-(S)-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

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。