(S)-1-((R)-2-Methoxy-1-phenyl-ethyl)-2-propyl-aziridine | 514168-47-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-1-((R)-2-Methoxy-1-phenyl-ethyl)-2-propyl-aziridine
• 英文别名: (2S)-1-[(1R)-2-methoxy-1-phenylethyl]-2-propylaziridine
• CAS: 514168-47-9
• 化学式: C₁₄H₂₁NO
• 分子量: 219.327
• InChiKey: IKKVPSZRBABABY-ZYOSVBKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  12.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  溶剂黄146 、 (S)-1-((R)-2-Methoxy-1-phenyl-ethyl)-2-propyl-aziridine 以 甲苯 为溶剂， 反应 4.0h， 以90%的产率得到(1S,1'R)-N-(2'-methoxy-1'-phenylethyl)-1-acetoxymethyl-2-methylpropylamine
  参考文献：
  名称：

  Regio- and Stereoselective Ring-Opening Reaction of Chiral Aziridines: A Facile Synthesis of Chiral β-Amino Alcohols

  摘要：

  The reaction of chiral 2-alkylsubstituted aziridines (1a-d) with acetic acid afforded beta-amino alcohols with an (S)-chiral center at the beta position (with respect to oxygen). In contrast, a reaction of the same chiral aziridines with acetyl chloride followed by treatment with water gave beta-amino alcohols that have an (S)-chiral center at the alpha position. In addition, the reaction of the same chiral aziridines with benzyl bromide followed by treatment with 2% sulfuric acid gave the beta-amino alcohols with an (R)-chiral center at the alpha position. Thus, we could control the regioselectivity and stereoselectivity of the ring-opening reaction of chiral aziridines (1a-d).

  DOI：

  10.3987/com-08-11537
• 作为产物：
  描述：

  (R)-(-)-2-甲氧基-1-苯乙胺 在 六甲基磷酰三胺 、 正丁基锂 、 magnesium sulfate 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 0.83h， 生成 (S)-1-((R)-2-Methoxy-1-phenyl-ethyl)-2-propyl-aziridine
  参考文献：
  名称：

  Facile Asymmetric Synthesis of Aziridine Derivatives via the Diastereoselective Reaction of Chiral Imines with Dimethylsulfonium Methylide

  摘要：

  A simple method for the synthesis of chiral 2-substituted aziridine derivatives is described. The reaction pathway consists of the diastereoselective addition of dimethylsulfonium methylide to chiral imines derived from (R)-phenylglycinol and various aldehydes.

  DOI：

  10.3987/com-02-s(m)32

文献信息

• Substituent Effects in Regio- and Stereoselective Ring-Opening Reaction of Aziridines with Et3N·3HF for β-Fluoroamine Synthesis
  作者：Shigeru Sasaki、Satono Watanabe、Kaori Shiino、Yuko Yanaka、Shiho Kaneko、Kana Miyamoto、Ayano Yasui、Hina Sakaino、Hiroyoshi Teramoto、Takayasu Yamauchi、Kimio Higashiyama

  DOI：10.3987/com-18-s(t)58

  日期：——

  This paper discusses the reactivity of various 2-substituted aziridine derivatives. The reaction of chiral 2-aryl-substituted aziridines with triethylamine trihydrofluoride (Et3N.3HF) afforded chiral beta-fluoroamines with high stereoselectivity. In contrast, the reaction of chiral 2-aliphatic-substituted aziridines with benzyl bromide, followed by treatment with Et3N.3HF, gave chiral beta-fluoroamines with high stereoselectivity.
• Regio- and Stereoselective Ring-Opening Reaction of Chiral Aziridines: A Facile Synthesis of Chiral β-Amino Alcohols
  作者：Kimio Higashiyama、Masataka Matsumura、Hiroshi Kojima、Takayasu Yamauchi

  DOI：10.3987/com-08-11537

  日期：——

  The reaction of chiral 2-alkylsubstituted aziridines (1a-d) with acetic acid afforded beta-amino alcohols with an (S)-chiral center at the beta position (with respect to oxygen). In contrast, a reaction of the same chiral aziridines with acetyl chloride followed by treatment with water gave beta-amino alcohols that have an (S)-chiral center at the alpha position. In addition, the reaction of the same chiral aziridines with benzyl bromide followed by treatment with 2% sulfuric acid gave the beta-amino alcohols with an (R)-chiral center at the alpha position. Thus, we could control the regioselectivity and stereoselectivity of the ring-opening reaction of chiral aziridines (1a-d).
• Facile Asymmetric Synthesis of Aziridine Derivatives via the Diastereoselective Reaction of Chiral Imines with Dimethylsulfonium Methylide
  作者：Kimio Higashiyama、Masataka Matsumura、Ayako Shiogama、Takayasu Yamauchi、Sigeru Ohmiya

  DOI：10.3987/com-02-s(m)32

  日期：——

  A simple method for the synthesis of chiral 2-substituted aziridine derivatives is described. The reaction pathway consists of the diastereoselective addition of dimethylsulfonium methylide to chiral imines derived from (R)-phenylglycinol and various aldehydes.