1H-Pyrido[3,4-b]indole-3-carboxylic acid,2,3,4,9-tetrahydro-1-[[(R)-(4-methylphenyl)sulfinyl]methyl]-, 1-methylethylester, (1S,3S)- | 391869-96-8

• 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: 1H-Pyrido[3,4-b]indole-3-carboxylic acid,2,3,4,9-tetrahydro-1-[[(R)-(4-methylphenyl)sulfinyl]methyl]-, 1-methylethylester, (1S,3S)-
• 英文别名: (trans,S_R)-isopropyl-1-(p-tolylsulfinylmethyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate
• CAS: 391869-96-8
• 化学式: C₂₃H₂₆N₂O₃S
• 分子量: 410.537
• InChiKey: HFFOTHRTXFIOFY-BNJCFXFUSA-N

物化性质

• 沸点：
  624.7±55.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.79
• 重原子数：
  29.0
• 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：
  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：

  1H-Pyrido[3,4-b]indole-3-carboxylic acid,2,3,4,9-tetrahydro-1-[[(R)-(4-methylphenyl)sulfinyl]methyl]-, 1-methylethylester, (1S,3S)- 在 镍 作用下， 以 甲醇 为溶剂， 以94%的产率得到isopropyl (1R,3S)-1-methyl-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
• 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 13.0h， 生成 1H-Pyrido[3,4-b]indole-3-carboxylic acid,2,3,4,9-tetrahydro-1-[[(R)-(4-methylphenyl)sulfinyl]methyl]-, 1-methylethylester, (1S,3S)-
  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.