(1S)-2-[(E)-1,2-dichloroethenoxy]-1-phenylethanamine

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1S)-2-[(E)-1,2-dichloroethenoxy]-1-phenylethanamine
• 化学式: C₁₀H₁₁Cl₂NO
• 分子量: 232.109
• InChiKey: OYAVZPAHRNTGFC-WPVMNKCKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-苄氧羰基-L-亮氨酰-L-亮氨酸 、 (1S)-2-[(E)-1,2-dichloroethenoxy]-1-phenylethanamine 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以77%的产率得到benzyl N-[(2S)-1-[[(2S)-1-[[(1S)-2-[(E)-1,2-dichloroethenoxy]-1-phenylethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate
  参考文献：
  名称：

  E-1,2-Dichlorovinyl ethers as irreversible protease inhibitors

  摘要：

  The synthesis of a novel motif for threonine protease inhibition is described. The desired E-1,2-dichlorovinyl ethers are obtained from alcohols and trichloroethylene as single diastereomers. Aqueous treatment at pH I I unmasks the hidden alpha-chloroacetate, which is required for the reaction with the active site of the protease. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.12.088
• 作为产物：
  描述：

  三氯乙烯 、 L-苯甘氨醇 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以57%的产率得到(1S)-2-[(E)-1,2-dichloroethenoxy]-1-phenylethanamine
  参考文献：
  名称：

  E-1,2-Dichlorovinyl ethers as irreversible protease inhibitors

  摘要：

  The synthesis of a novel motif for threonine protease inhibition is described. The desired E-1,2-dichlorovinyl ethers are obtained from alcohols and trichloroethylene as single diastereomers. Aqueous treatment at pH I I unmasks the hidden alpha-chloroacetate, which is required for the reaction with the active site of the protease. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.12.088

文献信息

• PEPTID-MIMETIKA UND IHRE VERWENDUNG ALS INHIBITOREN DES 20S PROTEASOMS, 26S PROTEASOMS UND DES IMMUNOPROTEASOMS
  申请人：Technische Universität Darmstadt

  公开号：EP1858913B1

  公开（公告）日：2010-09-01
• Mimetic Peptides and the Use Thereof in the Form of 20S, 26S and Immunoproteasome Inhitibors
  申请人：Schmidt Boris

  公开号：US20090012007A1

  公开（公告）日：2009-01-08

  The present invention relates to peptide-mimetic compounds, the synthesis and use thereof fort he inhibition of proteasomes and the induction of apoptosis in tumour cells. The present invention furthermore relates to pharmaceutical compositions comprising the compounds and the use of the compounds for a treatment of diseases, in particular cancer and neurodegenerative diseases.
• US8835392B2
  申请人：——

  公开号：US8835392B2

  公开（公告）日：2014-09-16
• E-1,2-Dichlorovinyl ethers as irreversible protease inhibitors
  作者：Boris Schmidt、Dennis K. Ehlert、Hannes A. Braun

  DOI：10.1016/j.tetlet.2003.12.088

  日期：2004.2

  The synthesis of a novel motif for threonine protease inhibition is described. The desired E-1,2-dichlorovinyl ethers are obtained from alcohols and trichloroethylene as single diastereomers. Aqueous treatment at pH I I unmasks the hidden alpha-chloroacetate, which is required for the reaction with the active site of the protease. (C) 2003 Elsevier Ltd. All rights reserved.