(S)-benzyl 2-(3-chloropropylamino)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-(3-chloropropylamino)propanoate
• 英文别名: benzyl (2S)-2-(3-chloropropylamino)propanoate
• 化学式: C₁₃H₁₈ClNO₂
• 分子量: 255.744
• InChiKey: UCYYKKHCHGPGSR-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-benzyl 2-(3-chloropropylamino)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 、 甲基叔丁基醚 、 水 、 异丙醇 为溶剂， 120.0 ℃ 、377.13 kPa 条件下， 反应 13.0h， 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：

  L-丙氨酸苄酯盐酸盐 、 1-溴-3-氯丙烷 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 74.0h， 以73%的产率得到(S)-benzyl 2-(3-chloropropylamino)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

• 1H-benzimidazole-4-carboxamides substituted with a quaternary carbon at the 2-position are potent PARP inhibitors
  申请人：Zhu Gui-Dong

  公开号：US20060229289A1

  公开（公告）日：2006-10-12

  Compounds of Formula (I) inhibit the PARP enzyme and are useful for treating a disease or a disorder associated with PARP. Also disclosed are pharmaceutical compositions comprising compounds of Formula (I), methods of treatment comprising compounds of Formula (I), and methods of inhibiting the PARP enzyme comprising compounds of Formula (I).

  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。
• 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 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
• Synthesis of (<i>R</i>)-Boc-2-methylproline via a Memory of Chirality Cyclization. Application to the Synthesis of Veliparib, a Poly(ADP-ribose) Polymerase Inhibitor
  作者：Lawrence Kolaczkowski、Jufang Barkalow、David M. Barnes、Anthony Haight、Wayne Pritts、Adam Schellinger

  DOI：10.1021/acs.joc.8b02866

  日期：2019.4.19

  (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.