(2R,2'R,1''R)-(1'-oxo-1',2',3',4'-tetrahydronaphthalen-2'-yl)-(1''-phenylethylamino)ethanoic acid | 847341-09-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (2R,2'R,1''R)-(1'-oxo-1',2',3',4'-tetrahydronaphthalen-2'-yl)-(1''-phenylethylamino)ethanoic acid
• 英文别名: (2R)-[(2R)-1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl]-{[(1R)-1-phenylethyl]amino}ethanoic acid；(2R)-2-[(2R)-1-oxo-3,4-dihydro-2H-naphthalen-2-yl]-2-[[(1R)-1-phenylethyl]amino]acetic acid
• CAS: 847341-09-7
• 化学式: C₂₀H₂₁NO₃
• 分子量: 323.392
• InChiKey: UIIREGQWDCNSPM-FSPWUOQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,2'R,1''R)-(1'-oxo-1',2',3',4'-tetrahydronaphthalen-2'-yl)-(1''-phenylethylamino)ethanoic acid 在 盐酸 、 sodium tetrahydroborate 、 manganese(ll) chloride 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 (3R,3aR,9bS)-3-((R)-1-Phenyl-ethylamino)-3a,4,5,9b-tetrahydro-3H-naphtho[1,2-b]furan-2-one; hydrochloride
  参考文献：
  名称：

  Crystallization-induced asymmetric transformation (CIAT) with simultaneous epimerization at two stereocenters. A short synthesis of conformationally constrained homophenylalanines

  摘要：

  CIAT of aza-Michael adducts allows simultaneous build up of two stereocenters. A consequent short and efficient synthesis affords simple access to the both antipodes of various conformationally restricted homophenylalanines. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.12.048
• 作为产物：
  描述：

  R(+)-alpha-甲基苄胺 、 2-(1,2,3,4-tetrahydro-1-oxo-2-naphthylidene)acetic acid 以 甲醇 、 水 为溶剂， 反应 120.0h， 以80%的产率得到(2R,2'R,1''R)-(1'-oxo-1',2',3',4'-tetrahydronaphthalen-2'-yl)-(1''-phenylethylamino)ethanoic acid
  参考文献：
  名称：

  Crystallization-induced asymmetric transformation (CIAT) with simultaneous epimerization at two stereocenters. A short synthesis of conformationally constrained homophenylalanines

  摘要：

  CIAT of aza-Michael adducts allows simultaneous build up of two stereocenters. A consequent short and efficient synthesis affords simple access to the both antipodes of various conformationally restricted homophenylalanines. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.12.048

文献信息

• The first example of a crystallization-induced asymmetric transformation (CIAT) in the Mannich reaction
  作者：Pavol Jakubec、Pavel Petráš、Andrej Ďuriš、Dušan Berkeš

  DOI：10.1016/j.tetasy.2009.12.014

  日期：2010.1

  The novel synthesis of highly enantioenriched N-substituted alpha-amino-gamma-alkyl(aryl)-gamma-oxoutanoic acids is described The process involves the combination of a crystallization-induced asymmetric transformation (CIAT) and the Mannich reaction The role of retro-Mannich and retro-Michael reactions in the mechanism of the highly stereoselective transformation is also discussed. (c) 2009 Elsevier Ltd All rights reserved