ethyl (R)-3-(tert-butoxycarbonylamino)-2-methylpropanoate | 187886-05-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl (R)-3-(tert-butoxycarbonylamino)-2-methylpropanoate
• 英文别名: Ethyl N-(t-Butyloxycarbonyl)-3-amino-2R-methylpropanoate；Ethyl N-BOC-3(R)-Methyl β-alanine；Ethyl (2R)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-methylpropanoate；ethyl (2R)-2-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 187886-05-1
• 化学式: C₁₁H₂₁NO₄
• 分子量: 231.292
• InChiKey: LWVJRJKVLTVHIH-MRVPVSSYSA-N

物化性质

• 沸点：
  319.0±25.0 °C(Predicted)
• 密度：
  1.021±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-甲基-3-[(苄基)氨基]丙酸乙酯 在 palladium on activated charcoal 正丁酸2,2,2-三氟乙酯 、 Candida antarctica Lipase A 、 氢气 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 24.0h， 生成 ethyl (R)-3-(tert-butoxycarbonylamino)-2-methylpropanoate
  参考文献：
  名称：

  Lipase-catalysed kinetic resolution in organic solvents: an approach to enantiopure α-methyl-β-alanine esters

  摘要：

  The Candida antarctica lipase A (CAL-A) and B (CAL-B)-catalysed resolutions of alpha-methyl-beta-alanine ethyl ester 1 wit neat ethyl and butyl butanoates and with 2,12-trifluoroethyl butanoate in organic solvents Were Studied, as were the alcoholyses in neat butanol and with methanol (0.8 M) in diisopropyl ether. The two enzymes, which display opposite (S for CAL-A and R for CAL-B) and low enantioselectivities (E=7-10), allowed the preparation of the two enantiomers in a two-step resolution protocol. The R enantiomer (ee=97%) was first separated as its Boc-protected derivative front the CAL-A-catalysed resolution mixture of (R)-1 and the enantiomerically enriched N-butanoylated counterpart. The enantiopurification of the latter gave the S enantiomer (ec=96%)) in the following CAL-B-catalysed 'interesterification' in butyl butanoate. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00478-0

文献信息

• Synthesis of enantiopure β2-homoalanine derivatives via rhodium catalyzed asymmetric hydrogenation
  作者：Susan Lühr、Jens Holz、Odalys Zayas、Oliver Seidelmann、Lutz Domke、Armin Börner

  DOI：10.1016/j.tetasy.2013.02.011

  日期：2013.4

  The stereoselective synthesis of chiral beta(2)-homoalanine derivatives with 99% ee by the Rh-catalyzed enantioselective hydrogenation of prochiral 2-aminomethyl acrylates is described. The subsequent transformation to chiral 3-amino-2-methylpropanols is also demonstrated. (c) 2013 Elsevier Ltd. All rights reserved.
• US5599947A
  申请人：——

  公开号：US5599947A

  公开（公告）日：1997-02-04
• US5670650A
  申请人：——

  公开号：US5670650A

  公开（公告）日：1997-09-23
• US5672769A
  申请人：——

  公开号：US5672769A

  公开（公告）日：1997-09-30
• US5719290A
  申请人：——

  公开号：US5719290A

  公开（公告）日：1998-02-17