(R)-N-p-tolylsulfinyl 2-(3,4-dimethoxy)phenylethylamine | 392662-71-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-N-p-tolylsulfinyl 2-(3,4-dimethoxy)phenylethylamine
• 英文别名: (R)-N-[2-(3,4-dimethoxyphenyl)ethyl]-4-methylbenzenesulfinamide
• CAS: 392662-71-4
• 化学式: C₁₇H₂₁NO₃S
• 分子量: 319.425
• InChiKey: WILHVVSBPBNZTF-JOCHJYFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-N-p-tolylsulfinyl 2-(3,4-dimethoxy)phenylethylamine 在 盐酸 、 三氟化硼乙醚 作用下， 以 乙醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 1.08h， 生成 鹿尾草定
  参考文献：
  名称：

  Enantiopure tetrahydroisoquinolines via N -sulfinyl Pictet–Spengler reactions

  摘要：

  Asymmetric Pictet-Spengler reactions with (R)-N-p-tolylsulfinyl-3,4-dimethoxyphenylethyl amine proceeded with high diastereo selectivity. Starting from the commercially available (R)- and (S)-Andersen reagents a highly efficient route to (+)- and (-)-salsolidine and related tetrahydroisoquinolines was developed. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01854-8
• 作为产物：
  描述：

  3,4-二甲氧基苯乙胺 、 (S_S)-menthyl p-toluenesulfinate 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.25h， 以85%的产率得到(R)-N-p-tolylsulfinyl 2-(3,4-dimethoxy)phenylethylamine
  参考文献：
  名称：

  Short stereoselective synthesis of (+)-crispine A via an N-sulfinyl Pictet–Spengler reaction

  摘要：

  We report the highly stereoselective synthesis of (R)-(+)-crispine A from the (R)-N-sulfinyl amine 1 by using a one-pot process involving the Pictet-Spengler reaction with 4-chlorobutanal, removal of the sulfinyl group by protonolysis of the N-S bond and in situ cyclization, with a 55% overall yield. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.01.121

文献信息

• Short stereoselective synthesis of (+)-crispine A via an N-sulfinyl Pictet–Spengler reaction
  作者：Rubén Sánchez-Obregón、Benjamín Ortiz、Virginia M. Mastranzo、Francisco Yuste、José Luis García Ruano

  DOI：10.1016/j.tetlet.2013.01.121

  日期：2013.4

  We report the highly stereoselective synthesis of (R)-(+)-crispine A from the (R)-N-sulfinyl amine 1 by using a one-pot process involving the Pictet-Spengler reaction with 4-chlorobutanal, removal of the sulfinyl group by protonolysis of the N-S bond and in situ cyclization, with a 55% overall yield. (C) 2013 Elsevier Ltd. All rights reserved.
• Enantiopure tetrahydroisoquinolines via N -sulfinyl Pictet–Spengler reactions
  作者：Christiaan Gremmen、Martin J Wanner、Gerrit-Jan Koomen

  DOI：10.1016/s0040-4039(01)01854-8

  日期：2001.12

  Asymmetric Pictet-Spengler reactions with (R)-N-p-tolylsulfinyl-3,4-dimethoxyphenylethyl amine proceeded with high diastereo selectivity. Starting from the commercially available (R)- and (S)-Andersen reagents a highly efficient route to (+)- and (-)-salsolidine and related tetrahydroisoquinolines was developed. (C) 2001 Elsevier Science Ltd. All rights reserved.