(S)-1-Benzo[1,3]dioxol-5-ylmethyl-propylamine | 103882-52-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (S)-1-Benzo[1,3]dioxol-5-ylmethyl-propylamine
• 英文别名: J (psychedelic), (S)-；(2S)-1-(1,3-benzodioxol-5-yl)butan-2-amine
• CAS: 103882-52-6
• 化学式: C₁₁H₁₅NO₂
• 分子量: 193.246
• InChiKey: VHMRXGAIDDCGDU-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

ADMET

代谢

苯并二氧杂环丁基丁胺（BDB）已知的人类代谢物包括DHABB。

Benzodioxolyl-butanamine (BDB) has known human metabolites that include DHABB.

来源:NORMAN Suspect List Exchange

反应信息

• 作为产物：
  描述：

  (R)-2-Amino-1-benzo[1,3]dioxol-5-yl-butan-1-ol 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 生成 (S)-1-Benzo[1,3]dioxol-5-ylmethyl-propylamine
  参考文献：
  名称：

  Stereoselective Synthesis of (S)-3,4-Methylenedioxyamphetamines from (R)-Cyanohydrins

  摘要：

  AbstractA stereoselective synthesis of (S)‐3,4‐methylenedioxyamphetamines (S)‐7, which are highly interesting as psychoactive compounds, is described. Starting from readily available (R)‐cyanohydrins (R)‐2 the 2‐amino‐1‐aryl alcohols (1R,2S)‐4 were obtained with high diastereoselectivity by addition of Grignard reagents to the O‐protected cyanohydrins (R)‐3, transimination of the addition products A with primary amines, and hydrogenation of the imino intermediates B with NaBH4. For the hydrogenation of the benzylic hydroxyl group in the 1,2‐amino alcohols (1R,2S)‐4 a new, very efficient method was developed. The optically pure amphetamines (S)‐7 were obtained under very mild conditions by catalytic hydrogenation of the oxazolidinones (4S,5R)‐6, which were readily available by phosgenation of the amino alcohols (1R,2S)‐4.

  DOI：

  10.1002/chem.19970030825