(1S,2R)-N-(2-amino-1,2-diphenylethyl)allyl carbamate | 1582815-25-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (1S,2R)-N-(2-amino-1,2-diphenylethyl)allyl carbamate
• 英文别名: prop-2-enyl N-[(1S,2R)-2-amino-1,2-diphenylethyl]carbamate
• CAS: 1582815-25-5
• 化学式: C₁₈H₂₀N₂O₂
• 分子量: 296.369
• InChiKey: NMFVFMLJZUGJCI-SJORKVTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯甲醛 在 ammonium acetate 作用下， 反应 77.0h， 生成 (1R,2S)-N-(2-amino-1,2-diphenylethyl)allyl carbamate 、 (1S,2R)-N-(2-amino-1,2-diphenylethyl)allyl carbamate
  参考文献：
  名称：

  Lipase-catalyzed desymmetrization of meso-1,2-diaryl-1,2-diaminoethanes

  摘要：

  The synthesis and enzyme-catalyzed desymmetrization of meso-1,2-diaryl-1,2-diaminoethanes have been investigated. A family of aromatic meso-1,2-diamines, containing different substitution patterns in the aromatic ring, was first prepared and then desymmetrized enantioselectively using lipases as biocatalysts. Selective alkoxycarbonylation of one of the amino groups was achieved using allyl carbonates, isolating the corresponding allyl monocarbamates with moderate to high enantiomeric excess at 45 degrees C. Candida antarctica lipase types A (CAL-A) and B (CAL-B) displayed the best activities and stereopreferences, with a dramatic influence being observed depending on the diamine structure. Non substituted and para-substituted aryldiamines led to the formation of allyl carbamates with good enantiomeric excess, using CAL-A for the less hindered substrates and CAL-B for the more hindered ones. On the other hand meta- and ortho-derivatives afforded low or negligible conversions and selectivities, respectively. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.01.007

文献信息

• Lipase-catalyzed desymmetrization of meso-1,2-diaryl-1,2-diaminoethanes
  作者：Daniel Méndez-Sánchez、Nicolás Ríos-Lombardía、Santiago García-Granda、José Montejo-Bernardo、Alfonso Fernández-González、Vicente Gotor、Vicente Gotor-Fernández

  DOI：10.1016/j.tetasy.2014.01.007

  日期：2014.2

  The synthesis and enzyme-catalyzed desymmetrization of meso-1,2-diaryl-1,2-diaminoethanes have been investigated. A family of aromatic meso-1,2-diamines, containing different substitution patterns in the aromatic ring, was first prepared and then desymmetrized enantioselectively using lipases as biocatalysts. Selective alkoxycarbonylation of one of the amino groups was achieved using allyl carbonates, isolating the corresponding allyl monocarbamates with moderate to high enantiomeric excess at 45 degrees C. Candida antarctica lipase types A (CAL-A) and B (CAL-B) displayed the best activities and stereopreferences, with a dramatic influence being observed depending on the diamine structure. Non substituted and para-substituted aryldiamines led to the formation of allyl carbamates with good enantiomeric excess, using CAL-A for the less hindered substrates and CAL-B for the more hindered ones. On the other hand meta- and ortho-derivatives afforded low or negligible conversions and selectivities, respectively. (C) 2014 Elsevier Ltd. All rights reserved.