benzyl 2-(tert-butoxycarbonylamino)-3-cyclopropylpropenoate | 849340-24-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl 2-(tert-butoxycarbonylamino)-3-cyclopropylpropenoate
• 英文别名: 2-tert-butoxycarbonylamino-3-cyclopropylacrylic acid benzyl ester；benzyl (Z)-3-cyclopropyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]prop-2-enoate
• CAS: 849340-24-5
• 化学式: C₁₈H₂₃NO₄
• 分子量: 317.385
• InChiKey: GAZPYWJXOBXFPU-PTNGSMBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl 2-(tert-butoxycarbonylamino)-3-cyclopropylpropenoate 在 palladium on activated charcoal 、 chiral rhodium-phosphinoferrocenylaminophosphine catalyst 氢气 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、68.95 kPa 条件下， 反应 1.0h， 生成 L-环丙基丙氨酸
  参考文献：
  名称：

  膦二茂铁基氨基膦是不对称催化的新型实用配体。

  摘要：

  [结构：见正文]在二茂铁基乙基主链上制备了一系列具有结构1所示的新颖膦-氨基膦连接设计的配体。结构2的这些BoPhoz配体在铑催化的脱氢α-氨基酸衍生物，衣康酸和α-酮酸酯的不对称氢化中提供了极高的活性和对映选择性。这些空气稳定的配体很容易从具有成本效益的非发火中间体中制备。

  DOI：

  10.1021/ol0261736
• 作为产物：
  描述：

  (Z)-2-(Benzoyl-tert-butoxycarbonyl-amino)-3-cyclopropyl-acrylic acid benzyl ester 在 一水合肼 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 4.0h， 以52%的产率得到benzyl 2-(tert-butoxycarbonylamino)-3-cyclopropylpropenoate
  参考文献：
  名称：

  The preparation of enantiomerically pure cyclopropylalanine

  摘要：

  Single enantiomer cyclopropylalanine (>99.9% ee) and various derivatives were prepared using an asymmetric hydrogenation approach with a rhodium catalyst based on the methyl BoPhox(TM) ligand. N-Boc cyclopropylalanine benzyl ester was the preferred derivative, as this material is ripe for further selective reaction and can be recrystallized to >99.5%, enantiomeric excess. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.07.007

文献信息

• Phosphinoferrocenylaminophosphines as Novel and Practical Ligands for Asymmetric Catalysis
  作者：Neil W. Boaz、Sheryl D. Debenham、Elaine B. Mackenzie、Shannon E. Large

  DOI：10.1021/ol0261736

  日期：2002.7.1

  series of ligands with a novel phosphine-aminophosphine ligation design as depicted in structure 1 has been prepared on a ferrocenylethyl backbone. These BoPhoz ligands of structure 2 have afforded exceedingly high activity and enantioselectivity in the rhodium-catalyzed asymmetric hydrogenation of dehydro-alpha-amino acid derivatives, itaconic acids, and alpha-ketoesters. These air-stable ligands are readily

  [结构：见正文]在二茂铁基乙基主链上制备了一系列具有结构1所示的新颖膦-氨基膦连接设计的配体。结构2的这些BoPhoz配体在铑催化的脱氢α-氨基酸衍生物，衣康酸和α-酮酸酯的不对称氢化中提供了极高的活性和对映选择性。这些空气稳定的配体很容易从具有成本效益的非发火中间体中制备。
• Synthesis and Application of Phosphinoferrocenylaminophosphine Ligands for Asymmetric Catalysis
  作者：Neil W. Boaz、Elaine B. Mackenzie、Sheryl D. Debenham、Shannon E. Large、James A. Ponasik

  DOI：10.1021/jo048312y

  日期：2005.3.1

  [GRAPHICS]A new class of bidentate ligands utilizing a phosphine-aminophosphine structure has been prepared on a ferrocenylethyl backbone in a straightforward and scalable fashion from acetylferrocene. The unique property of the alpha-ferrocenyl carbonium ion that allows the replacement of a variety of "leaving groups" with retention of configuration greatly facilitates the synthesis, and a number of ligands have been prepared by varying the nitrogen and phosphorus substituents on the aminophosphine. These readily prepared phosphinoferrocenylaminophosphines, known as BoPhoz ligands, show surprising hydrolytic and air stability, with no degradation after 3 years open to the air. The rhodium complexes of these ligands show exceedingly high enantioselectivities (generally >95% ee) and activities often in excess of 50 000 catalyst turnovers per hour for the asymmetric hydrogenation of a wide variety of dehydro-alpha-amino acid and itaconic acid derivatives. They also show high activity and good to excellent enantioselectivity for the hydrogenation of a number of alpha-ketoesters.
• A versatile synthesis of phosphine–aminophosphine ligands for asymmetric catalysis
  作者：Neil W. Boaz、James A. Ponasik、Shannon E. Large

  DOI：10.1016/j.tetasy.2005.05.014

  日期：2005.6

  A new and versatile synthesis of phosphine-aminophosphine ligands allows the incorporation of a wide range of nitrogen and phosphorus substituents into these ligands, several of which exhibit improved properties for rhodium-catalyzed asymmetric hydrogenation reactions. This synthesis also allows the preparation of mixed phosphine-phosphoramidite species. (c) 2005 Elsevier Ltd. All rights reserved.
• PREPARATION OF AMINOPHOSPHINES
  申请人：JOHNSON MATTHEY PUBLIC LIMITED COMPANY

  公开号：EP1758845B1

  公开（公告）日：2008-12-03
• US6906213B1
  申请人：——

  公开号：US6906213B1

  公开（公告）日：2005-06-14