(trans,SR)-methyl-1-(p-tolylsulfinylmethyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate | 391869-94-6

• 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: (trans,SR)-methyl-1-(p-tolylsulfinylmethyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate
• 英文别名: (trans,S_R)-methyl-1-(p-tolylsulfinylmethyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate
• CAS: 391869-94-6
• 化学式: C₂₁H₂₂N₂O₃S
• 分子量: 382.483
• InChiKey: HTCDCWYEPIRSSE-DSNGTPCMSA-N

物化性质

• 熔点：
  215 °C
• 沸点：
  617.1±55.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  71.19
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (trans,SR)-methyl-1-(p-tolylsulfinylmethyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate 在 镍 作用下， 以 甲醇 为溶剂， 以75%的产率得到methyl (1R,3S)-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
  参考文献：
  名称：

  2-(Arylsulfinylmethyl)oxazinanes: chiral carbonyl equivalents. Application to the asymmetric synthesis of 1,2,3,4-tetrahydro-β-carbolines

  摘要：

  2-(p-Tolylsulfinylmethyl)oxazinane, a chiral carbonyl equivalent, has been synthesised and used for the diastereoselective synthesis of tetrahydro-beta-carbolines including intermediates of yohimbine and herman alkaloids. A fair degree of diastereoselectivity, comparable with other approaches, has been achieved. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.07.062
• 作为产物：
  描述：

  4,4,6-Trimethyl-2-((R)-toluene-4-sulfinylmethyl)-5,6-dihydro-4H-[1,3]oxazine 在 盐酸 、 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 水 、 乙腈 为溶剂， 反应 11.0h， 生成 (trans,SR)-methyl-1-(p-tolylsulfinylmethyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate
  参考文献：
  名称：

  2-(Arylsulfinylmethyl)oxazinanes: chiral carbonyl equivalents. Application to the asymmetric synthesis of 1,2,3,4-tetrahydro-β-carbolines

  摘要：

  2-(p-Tolylsulfinylmethyl)oxazinane, a chiral carbonyl equivalent, has been synthesised and used for the diastereoselective synthesis of tetrahydro-beta-carbolines including intermediates of yohimbine and herman alkaloids. A fair degree of diastereoselectivity, comparable with other approaches, has been achieved. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.07.062

文献信息

• 2-Arylsulfinylmethyloxazines: Chiral Carbonyl Equivalents
  作者：Kamaljit Singh、Prasant K. Deb、Sonia Behal

  DOI：10.3987/com-01-9263

  日期：——

  A single pot acid catalysed condensation reaction of 2-arylsulfinylmethyloxazinane - a chiral carbonyl equivalent (derived from the title oxazine by BH4- reduction) with tryptamine and tryptophan esters, furnishes tetrahydro-beta -carbolines and can be subsequently transformed into indole alkaloids.