(2S)-2-tert-butoxycarbonylamino-3-cyclopropyl-propionic acid benzyl ester | 406681-37-6

• 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: (2S)-2-tert-butoxycarbonylamino-3-cyclopropyl-propionic acid benzyl ester
• 英文别名: N-tert-butyloxycarbonyl cyclopropylalanine benzyl ester；(S)-2-tert-butoxycarbonylamino-3-cyclopropylpropionic acid benzyl ester；(S)-N-t-butoxycarbonylcyclopropylalanine benzyl ester；N-tert-butoxycarbonyl L-cyclopropylalanine benzyl ester；benzyl (2S)-3-cyclopropyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 406681-37-6
• 化学式: C₁₈H₂₅NO₄
• 分子量: 319.401
• InChiKey: ZAYJNJQDNXWDKH-HNNXBMFYSA-N

物化性质

• 熔点：
  52-54°C
• 稳定性/保质期：
  避氧化物

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2922509090
• 安全说明：
  S24/25

反应信息

• 作为反应物：
  描述：

  (2S)-2-tert-butoxycarbonylamino-3-cyclopropyl-propionic acid benzyl ester 在 palladium on activated charcoal 氢气 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 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：

  (2S)-2-tert-butoxycarbonylamino-4-cyclopropanecarbonylperoxy-4-oxo-butyric acid benzyl ester 反应 30.0h， 以52%的产率得到(2S)-2-tert-butoxycarbonylamino-3-cyclopropyl-propionic acid benzyl ester
  参考文献：
  名称：

  通过二酰基过氧化物的光解合成β-环丙基丙氨酸。

  摘要：

  [反应：参见正文] 254纳米（无溶剂）衍生自环丙烷羧酸和l-天冬氨酸的纯净（不溶剂）不对称二酰基过氧化物的光解以合理的收率生成了受保护的β-环丙基丙氨酸。通过这种方法，可以合成抗肿瘤药物贝洛糖素A的关键成分的正交保护的3-（反式-2-氨基环丙基）丙氨酸（21）和牙买加呕吐病的病原体受保护的次糖苷A（26）。中间取代的环丙基自由基的偶联主要在保留构型的情况下进行（dr>或= 95：5）。

  DOI：

  10.1021/ol035859a

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。
• Preparation of aminophosphines
  申请人：Boaz Neil Warren

  公开号：US06906213B1

  公开（公告）日：2005-06-14

  Disclosed is a process for the preparation of phosphine-aminophosphines that are useful in the formation of catalysts useful in carrying out a wide variety of reactions such as asymmetric hydrogenations, asymmetric reductions, asymmetric hydroborations, asymmetric olefin isomerizations, asymmetric hydrosilations, asymmetric allylations, asymmetric conjugate additions, and asymmetric organometallic additions. The process comprises the steps of (1) contacting a compound of formula 2 R 2 P—L—NHR 3 2 with phosphorus trihalide PX 3 in the presence of an inert, organic solvent and an acid acceptor to produce intermediate compound having formula 3 (2) contacting intermediate compound 3 with a reactant having the formula R 1 —M 1 , R 2 —M 1 or a mixture thereof.

  揭示了一种制备磷胺磷酸胺的过程，这些物质在催化剂的形成中非常有用，可用于进行各种反应，如不对称氢化、不对称还原、不对称氢硼化、不对称烯烃异构化、不对称硅氢化、不对称烯基化、不对称共轭加成和不对称有机金属加成。该过程包括以下步骤：(1)在惰性有机溶剂和酸性受体的存在下，将化合物2R2P—L—NHR32与磷三卤化物PX3接触，以产生具有公式3的中间化合物；(2)将中间化合物3与具有公式R1—M1、R2—M1或两者的混合物的反应物接触。
• Acylated nonadepsipeptides
  申请人：Von Nussbaum Franz

  公开号：US20050075281A1

  公开（公告）日：2005-04-07

  The invention relates to nonadepsipeptides and process for their preparation, and to their use for producing medicaments for the treatment and/or prophylaxis of diseases, in particular bacterial infectious diseases.

  本发明涉及非脂肪酰二肽类化合物及其制备方法，以及它们用于生产治疗和/或预防疾病，特别是细菌感染性疾病的药物的用途。
• 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.