benzyl 3,6-diazabicyclo[3.1.0]hexane-3-carboxylate | 31865-26-6

• 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: benzyl 3,6-diazabicyclo[3.1.0]hexane-3-carboxylate
• 英文别名: 3,6-diaza-bicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester；3-Cbz-3,6-diazabicyclo[3.1.0]hexane
• CAS: 31865-26-6
• 化学式: C₁₂H₁₄N₂O₂
• 分子量: 218.255
• InChiKey: VBWHAKLFNAOALS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  51.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-甲氧基吡啶-2-甲酸 、 benzyl 3,6-diazabicyclo[3.1.0]hexane-3-carboxylate 在 N,N'-羰基二咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以65%的产率得到3-carbobenzyloxy-6-(4-methoxypicolinoyl)-3,6-diazabicyclo[3.1.0]hexane
  参考文献：
  名称：

  Cinchona Alkaloid Amides/Dialkylzinc Catalyzed Enantioselective Desymmetrization of Aziridines with Phosphites

  摘要：

  The first highly enantioselective desymmetrization of aziridines with phosphites has been developed. Excellent yields and enantio-selectivities were observed for the reaction with various aziridines using a new class of readily accessible chiral catalysts derived from 9-amino-9-deoxy-epi-cinchonas alkaloids. In studies probing the reaction mechanism, we observed some complexes for the cinchona alkaloid amide-Zn(II) by ESI-MS analysis

  DOI：

  10.1021/ja309963w
• 作为产物：
  描述：

  benzyl (3S,4S)-3-azido-4-methylsulfonyloxypyrrolidine-1-carboxylate 在 2,2'-联吡啶 、 cobalt(II) bromide sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以97%的产率得到benzyl 3,6-diazabicyclo[3.1.0]hexane-3-carboxylate
  参考文献：
  名称：

  Enantioselective ring-opening of aziridines

  摘要：

  一种制备环氧丙烷和亲核试剂的亲核加成产物的方法，该方法包括在双芳基磷酸催化剂存在下处理环氧丙烷和亲核试剂。

  公开号：

  US20090030212A1

文献信息

• Enantioselective fluoride ring opening of aziridines enabled by cooperative Lewis acid catalysis
  作者：Julia A. Kalow、Abigail G. Doyle

  DOI：10.1016/j.tet.2013.01.062

  日期：2013.7

  The enantioselective ring opening of aziridines using a latent source of HF is described. A combination of two Lewis acids, (salen)Co and an achiral Ti(IV) cocatalyst, provided optimal reactivity and enantioselectivity for the trans beta-fluoroamine product. The use of a chelating aziridine protecting group was crucial. Acyclic and cyclic meso N-picolinamide aziridines underwent fluoride ring opening in up to 84% ee, and the kinetic resolution of a piperidine-derived aziridine was performed with k(rel)=6.6. The picolinamide group may be readily removed without epimerization of the fluoroamine. Preliminary studies revealed a bimetallic mechanism wherein the chiral (salen)Co catalyst delivers the nucleophile and the Ti(IV) cocatalyst activates the aziridine. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis of β-Fluoroamines by Lewis Base Catalyzed Hydrofluorination of Aziridines
  作者：Julia A. Kalow、Dana E. Schmitt、Abigail G. Doyle

  DOI：10.1021/jo300433a

  日期：2012.4.20

  Lewis base catalysis promotes the in situ generation of amine-HF reagents from benzoyl fluoride and a non-nucleophilic alcohol. The hydrofluorination of aziridines to provide beta-fluoroamines using this latent HF source is described. This protocol displays a broad scope with respect to aziridine substitution and N-protecting groups. Examples of regio- and diastereoselective ring opening to access medicinally relevant beta-fluoroamine building blocks are presented.
• US7799934B2
  申请人：——

  公开号：US7799934B2

  公开（公告）日：2010-09-21
• [EN] ANTI-OSTEOARTHRITIS COMPOUNDS AND RELATED COMPOSITIONS AND METHODS<br/>[FR] COMPOSÉS ANTI-OSTÉOARTHRITE AINSI QUE COMPOSITIONS ET MÉTHODES ASSOCIÉES
  申请人：AVIDENCE THERAPEUTICS INC

  公开号：WO2021011720A2

  公开（公告）日：2021-01-21

  This invention provides two genuses of novel compounds. Compounds in each genus inhibit both aggrecanase 1 (Adamts4) and aggrecanase 2 (Adamts5). This invention also provides related compositions and methods for treating inflammatory diseases, diseases involving degradation of cartilage, and diseases involving the disruption of cartilage homeostasis.
• Enantioselective ring-opening of aziridines
  申请人：Antilla Jon C.

  公开号：US20090030212A1

  公开（公告）日：2009-01-29

  A process for the preparation of a nucleophilic addition product of an aziridine and a nucleophile, the process comprising treating the arizidine with the nucleophile in the presence of a biaryl phosphoric acid catalyst

  一种制备环氧丙烷和亲核试剂的亲核加成产物的方法，该方法包括在双芳基磷酸催化剂存在下处理环氧丙烷和亲核试剂。