(S)-benzyl 2-((tert-butoxycarbonyl)(3-chloropropyl)amino)propanoate

• 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: (S)-benzyl 2-((tert-butoxycarbonyl)(3-chloropropyl)amino)propanoate
• 英文别名: benzyl (2S)-2-[3-chloropropyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]propanoate
• 化学式: C₁₈H₂₆ClNO₄
• 分子量: 355.862
• InChiKey: VOABLWASPRMXSY-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-benzyl 2-((tert-butoxycarbonyl)(3-chloropropyl)amino)propanoate 在 盐酸 、 5%-palladium/activated carbon 、 氢气 、 sodium acetate 、 sodium carbonate 、 溶剂黄146 、 N,N'-羰基二咪唑 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 乙醇 、 水 、 异丙醇 为溶剂， 120.0 ℃ 、377.13 kPa 条件下， 反应 12.0h， 生成 2-[(2R)-2-甲基-2-吡咯烷基]-1H-苯并咪唑-7-甲酰胺
  参考文献：
  名称：

  Synthesis of (R)-Boc-2-methylproline via a Memory of Chirality Cyclization. Application to the Synthesis of Veliparib, a Poly(ADP-ribose) Polymerase Inhibitor

  摘要：

  (R)-Boc-2-methylproline (3a) was synthesized in good yield with excellent stereochemical control from alanine benzyl ester hydrochloride 11. The process, which is based on a modification of one described by Kawabata, proceeds in four steps and requires no chromatography. The product (R)-Boc-2-methylproline (3a) was then carried forward in three steps to produce veliparib 1, a poly(ADP-ribose) polymerase inhibitor.

  DOI：

  10.1021/acs.joc.8b02866
• 作为产物：
  描述：

  (S)-benzyl 2-(3-chloropropylamino)propanoate 、 二碳酸二叔丁酯 在 N,N-二甲基乙二胺 作用下， 以 甲基叔丁基醚 为溶剂， 以96%的产率得到(S)-benzyl 2-((tert-butoxycarbonyl)(3-chloropropyl)amino)propanoate
  参考文献：
  名称：

  1H-benzimidazole-4-carboxamides substituted with a quaternary carbon at the 2-position are potent PARP inhibitors

  摘要：

  公式(I)的化合物抑制PARP酶，并且对于治疗与PARP相关的疾病或障碍是有用的。还披露了包括公式(I)化合物的药物组合物、包括公式(I)化合物的治疗方法，以及包括公式(I)化合物的抑制PARP酶的方法。

  公开号：

  US20060229289A1

文献信息

• METHOD OF PRODUCING OPTICALLY ACTIVE N-(HALOPROPYL)AMINO ACID DERIVATIVE
  申请人：Nagase & Co., Ltd.

  公开号：EP2192110A1

  公开（公告）日：2010-06-02

  The present invention provides a method for producing an optically active N-(halopropyl)amino acid derivative, wherein the method comprises the steps of obtaining a compound represented by formula (III) by reacting an optically active alanine ester represented by formula (I) or a salt thereof (hereinafter sometimes simply referred to as an "alanine ester") with a halogenated propane represented by formula (II); and obtaining an optically active N-(halopropyl)amino acid derivative represented by formula (IV) by introducing a protecting group onto the nitrogen atom of the compound represented by formula (III). The present invention provides a method for efficiently producing an optically active N-(halopropyl)amino acid derivative.

  本发明提供了一种生产光学活性N-(卤丙基)氨基酸衍生物的方法，其中该方法包括以下步骤：通过使式(I)代表的光学活性丙氨酸酯或其盐(以下有时简称为 "丙氨酸酯")与式(II)代表的卤代丙烷反应，得到式(III)代表的化合物；通过在式(III)代表的化合物的氮原子上引入保护基团，获得式(IV)代表的具有光学活性的N-(卤代丙基)氨基酸衍生物。本发明提供了一种高效生产光学活性 N-(卤丙基)氨基酸衍生物的方法。
• METHOD FOR PRODUCING OPTICALLY ACTIVE 2-METHYLPROLINE DERIVATIVE
  申请人：Kaneka Corporation

  公开号：EP2735560A1

  公开（公告）日：2014-05-28

  An optically active 2-methylproline derivative is produced by forming a salt from a racemic 2-methylproline derivative and an optically active 1-arylethylamine derivative and precipitating the salt in a form of solid from a solvent.

  一种具有光学活性的 2-甲基脯氨酸衍生物是通过外消旋 2-甲基脯氨酸衍生物和具有光学活性的 1-芳基乙胺衍生物形成盐，并从溶剂中沉淀出固体形式的盐而制成的。
• METHOD OF PRODUCING OPTICALLY ACTIVE N-(HALOPROPYL) AMINO ACID DERIVATIVE
  申请人：Matsumoto Jun

  公开号：US20110190527A1

  公开（公告）日：2011-08-04

  The present invention provides a method for producing an optically active N-(halopropyl)amino acid derivative, wherein the method comprises the steps of obtaining a compound represented by formula (III) by reacting an optically active alanine ester represented by formula (I) or a salt thereof (hereinafter sometimes simply referred to as an “alanine ester”) with a halogenated propane represented by formula (II); and obtaining an optically active N-(halopropyl)amino acid derivative represented by formula (IV) by introducing a protecting group onto the nitrogen atom of the compound represented by formula (III). The present invention provides a method for efficiently producing an optically active N-(halopropyl)amino acid derivative.
• US8242303B2
  申请人：——

  公开号：US8242303B2

  公开（公告）日：2012-08-14