3-benzyl-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3-benzyl-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester
• 英文别名: Ethyl trans-3-benzyl-2,4-dioxo-3-aza-bicyclo[3.1.0]hexane-6-carboxylate；ethyl (1R,5S)-3-benzyl-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carboxylate
• 化学式: C₁₅H₁₅NO₄
• 分子量: 273.288
• InChiKey: SFFQYGDIFWFUAF-FOSCPWQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-benzyl-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester 以83的产率得到((1R,5S,6S)-3-苯甲基-3-氮杂二环[3.1.0]己烷-6-基)甲醇
  参考文献：
  名称：

  Azabicyclo quinolone and naphthyridinone carboxylic acids

  摘要：

  含有氮杂双环基团的喹诺酮羧酸衍生物具有抗菌活性。

  公开号：

  US05164402A1
• 作为产物：
  描述：

  吡咯并[3,4-c]吡唑-3-羧酸,1,3a,4,5,6,6a-六氢-4,6-二羰基-5-(苯基甲基)-,乙基酯 以35的产率得到3-benzyl-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester
  参考文献：
  名称：

  Azabicyclo quinolone and naphthyridinone carboxylic acids

  摘要：

  含有氮杂双环基团的喹诺酮羧酸衍生物具有抗菌活性。

  公开号：

  US05164402A1

文献信息

• Development of Multikilogram Continuous Flow Cyclopropanation of <i>N</i>-Benzylmaleimide through Kinetic Analysis
  作者：Frederic G. Buono、Magnus C. Eriksson、Bing-Shiou Yang、Suresh R. Kapadia、Heewon Lee、Jason Brazzillo、Jon C. Lorenz、Laurence Nummy、Carl A. Busacca、Nathan Yee、Chris Senanayake

  DOI：10.1021/op500263m

  日期：2014.11.21

  A convenient and high-yielding method for the synthesis of trans-(dioxo)-azabicyclo-[3.1.0]-hexane carboxylate, a key intermediate of complex molecules, is presented using a flow cyclopropanation process. From a detailed kinetic study, it is demonstrated that the reaction concentration, addition time of reagents, and initial mixing temperature are the critical parameters to minimize formation of byproducts and to get high reaction yield. Using a modular tubular flow reactor, the trans/cis-(dioxo)-azabicyclo-[3.1.0]-hexane carboxylate was obtained in 92% yield and isomerized under basic conditions to produce the trans-isomer in greater than 99% diastereomeric excess. Using this approach, the reaction yield was significantly increased compared to the batch process, and the robustness and reproducibility of this flow process was demonstrated for the synthesis of this key intermediate on a multikilogram scale.
• Drug. Future 1996, 21, 496
  作者：

  DOI：——

  日期：——
• FUMAGILLOL SPIROCYCLIC COMPOUNDS AND FUSED BICYCLIC COMPOUNDS AND METHODS OF MAKING AND USING SAME
  申请人：Zafgen, Inc.

  公开号：US20180079737A1

  公开（公告）日：2018-03-22

  Disclosed herein, in part, are fumagillol compounds and methods of use in treating medical disorders, such as obesity. Pharmaceutical compositions and methods of making fumagillol compounds are provided. The compounds are contemplated to have activity against methionyl aminopeptidase 2.
• US9944613B2
  申请人：——

  公开号：US9944613B2

  公开（公告）日：2018-04-17