N-(diphenylmethylene)-1-(ethoxycarbonyl)cyclopropanamine

• 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: N-(diphenylmethylene)-1-(ethoxycarbonyl)cyclopropanamine
• 英文别名: Ethyl 1-(benzhydrylideneamino)cyclopropane-1-carboxylate
• 化学式: C₁₉H₁₉NO₂
• 分子量: 293.365
• InChiKey: AWPQNJZDPDRFMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(diphenylmethylene)-1-(ethoxycarbonyl)cyclopropanamine 在 盐酸 作用下， 以 水 为溶剂， 以8.7 g的产率得到1-氨基环丙烷羧酸乙酯
  参考文献：
  名称：

  [EN] PROCESS FOR THE PREPARATION OF CYCLOPROPYLDIKETOPIPERAZINES AND OF A KEY INTERMEDIATE OF DS-5272
  [FR] PROCÉDÉ DE PRÉPARATION DE CYCLOPROPYLDICÉTOPIPÉRAZINES ET D'UN INTERMÉDIAIRE CLÉ DE DS-5272

  摘要：

  本发明的目的是改进环丙基二酮哌啶及其关键中间体的制备过程。

  公开号：

  WO2018145860A1
• 作为产物：
  描述：

  二苯甲酮亚胺 、 1-氨基环丙烷羧酸乙酯 在 3 A molecular sieve 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以90%的产率得到N-(diphenylmethylene)-1-(ethoxycarbonyl)cyclopropanamine
  参考文献：
  名称：

  The N-Cyclopropylimine-1-pyrroline Photorearrangement as a Synthetic Tool:  Scope and Limitations

  摘要：

  [GRAPHICS]The scope and limitations of the photorearrangement of N-cyclopropylimines to 1-pyrrolines are presented. The influence on the reactivity of different substituents throughout the cyclopropane ring and at the iminic position of the N-cyclopropylimine structure is discussed. The observed effects are interpreted from computational studies. The principal findings relate to (1) the enhanced reactivity of 1-substituted compounds toward rearrangement, (2) the lack of reactivity of crowded cyclopropanes, and (3) the high chemoselectivity of the process.

  DOI：

  10.1021/jo050871x

文献信息

• Process for the preparation of cyclopropyldiketopiperazines and of a key intermediate of DS-5272
  申请人：F.I.S.—Fabbrica Italiana Sintetici S.p.A.

  公开号：US10836778B2

  公开（公告）日：2020-11-17

  Object of the present invention is an improved process for the preparation of cyclopropyldiketopiperazines and thereof key intermediates.

  本发明的目的是改进环丙基二酮哌嗪及其关键中间体的制备工艺。
• Potent ketoamide inhibitors of HCV NS3 protease derived from quaternized P1 groups
  作者：Srikanth Venkatraman、Francisco Velazquez、Wanli Wu、Melissa Blackman、Vincent Madison、F. George Njoroge

  DOI：10.1016/j.bmcl.2010.02.051

  日期：2010.4

  Blood borne hepatitis C infections are the primary cause for liver cirrhosis and hepatocellular carcinoma. HCV NS3 protease, a pivotal enzyme in the replication cycle of HCV virus has been the primary target for development of new drug candidates. Boceprevir and telaprevir are two novel ketoamide derived inhibitors that are currently undergoing phase-III clinical trials. These inhibitors include ketoamide functionality as serine trap and have an acidic alpha-ketoamide center that undergoes epimerization under physiological conditions. Our initial attempts to arrest this epimerization by introducing quaternary amino acids at P-1 had resulted in significantly diminished activity. In this manuscript we describe alpha quaternized P-1 group that result in potent inhibitors in the enzyme assay and demonstrate cellular activity comparable to boceprevir. (C) 2010 Elsevier Ltd. All rights reserved.
• PROCESS FOR THE PREPARATION OF CYCLOPROPYLDIKETOPIPERAZINES AND OF A KEY INTERMEDIATE OF DS-5272
  申请人：F.I.S.- Fabbrica Italiana Sintetici S.p.A.

  公开号：EP3580205B1

  公开（公告）日：2021-05-05
• The <i>N</i>-Cyclopropylimine-1-pyrroline Photorearrangement as a Synthetic Tool:  Scope and Limitations
  作者：Alberto Soldevilla、Diego Sampedro、Pedro J. Campos、Miguel A. Rodríguez

  DOI：10.1021/jo050871x

  日期：2005.8.1

  [GRAPHICS]The scope and limitations of the photorearrangement of N-cyclopropylimines to 1-pyrrolines are presented. The influence on the reactivity of different substituents throughout the cyclopropane ring and at the iminic position of the N-cyclopropylimine structure is discussed. The observed effects are interpreted from computational studies. The principal findings relate to (1) the enhanced reactivity of 1-substituted compounds toward rearrangement, (2) the lack of reactivity of crowded cyclopropanes, and (3) the high chemoselectivity of the process.
• [EN] PROCESS FOR THE PREPARATION OF CYCLOPROPYLDIKETOPIPERAZINES AND OF A KEY INTERMEDIATE OF DS-5272<br/>[FR] PROCÉDÉ DE PRÉPARATION DE CYCLOPROPYLDICÉTOPIPÉRAZINES ET D'UN INTERMÉDIAIRE CLÉ DE DS-5272
  申请人：FIS FABBRICA ITALIANA SINTETICI SPA

  公开号：WO2018145860A1

  公开（公告）日：2018-08-16

  Object of the present invention is an improved process for the preparation of cyclopropyldiketopiperazines and thereof key intermediates.

  本发明的目的是改进环丙基二酮哌啶及其关键中间体的制备过程。