N-benzyl-2-bromocyclopropanecarboxamide | 1296205-13-4

• 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-benzyl-2-bromocyclopropanecarboxamide
• 英文别名: N-benzyl-2-bromocyclopropane-1-carboxamide
• CAS: 1296205-13-4
• 化学式: C₁₁H₁₂BrNO
• 分子量: 254.126
• InChiKey: ZPNPCJZZUPGUHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  吲哚 、 N-benzyl-2-bromocyclopropanecarboxamide 在 18-冠醚-6 、 potassium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以50%的产率得到
  参考文献：
  名称：

  Formal Substitution of Bromocyclopropanes with Nitrogen Nucleophiles

  摘要：

  A highly chemo- and diastereoselective protocol toward amino-substituted donor acceptor cyclopropanes via the formal nucleophilic displacement in bromocyclopropanes is described. A wide range of N-nucleophiles, including carboxamides, sulfonamides, azoles, and anilines, can be efficiently employed in this transformation, providing expeditious access to stereochemically defined and densely functionalized cydopropylamine derivatives.

  DOI：

  10.1021/jo4011798
• 作为产物：
  描述：

  2-bromocyclopropanecarbonyl chloride 、 苄胺 以 四氢呋喃 为溶剂， 反应 1.0h， 以89%的产率得到N-benzyl-2-bromocyclopropanecarboxamide
  参考文献：
  名称：

  基于氧和硫的亲核试剂在溴环丙烷的形式亲核取代中的非对映选择性控制

  摘要：

  描述了基于氧和硫的亲核试剂对溴环丙烷的非对映收敛形式亲核取代。该反应通过原位形成高反应性的环丙烯中间体并随后通过应变的C═C键非对映选择性地添加亲核试剂而进行。已经证明了三种控制加成的非对映选择性的替代方法：（1）热力学驱动可烯丙基羧酰胺的差向异构化；（2）通过大取代基的空间控制；和（3）羧酰胺或羧酸酯官能团的导向作用。

  DOI：

  10.1021/jo200368a

文献信息

• Formal Nucleophilic Substitution of Bromocyclopropanes with Azoles
  作者：Pavel Ryabchuk、Marina Rubina、Jack Xu、Michael Rubin

  DOI：10.1021/ol300352z

  日期：2012.4.6

  A highly diastereoselective protocol for the formal nucleophilic substitution of 2-bromocyclopropylcarboxamides with azoles is described. A wide range of azoles, including pyrroles, indoles, benzimidazoles, pyrazoles, and benzotriazoles, can be efficiently employed as pronucleophiles in this transformation, providing expeditious access to N-cyclopropyl heterocycles.
• Diastereoselectivity Control in Formal Nucleophilic Substitution of Bromocyclopropanes with Oxygen- and Sulfur-Based Nucleophiles
  作者：Joseph E. Banning、Anthony R. Prosser、Bassam K. Alnasleh、Jason Smarker、Marina Rubina、Michael Rubin

  DOI：10.1021/jo200368a

  日期：2011.5.20

  diastereoconvergent formal nucleophilic substitution of bromocyclopropanes with oxygen- and sulfur-based nucleophiles is described. The reaction proceeds via in situ formation of a highly reactive cyclopropene intermediate and subsequent diastereoselective addition of a nucleophile across the strained C═C bond. Three alternative means of controlling the diastereoselectivity of addition have been demonstrated:

  描述了基于氧和硫的亲核试剂对溴环丙烷的非对映收敛形式亲核取代。该反应通过原位形成高反应性的环丙烯中间体并随后通过应变的C═C键非对映选择性地添加亲核试剂而进行。已经证明了三种控制加成的非对映选择性的替代方法：（1）热力学驱动可烯丙基羧酰胺的差向异构化；（2）通过大取代基的空间控制；和（3）羧酰胺或羧酸酯官能团的导向作用。
• Formal Substitution of Bromocyclopropanes with Nitrogen Nucleophiles
  作者：Joseph E. Banning、Jacob Gentillon、Pavel G. Ryabchuk、Anthony R. Prosser、Andrew Rogers、Andrew Edwards、Andrew Holtzen、Ivan A. Babkov、Marina Rubina、Michael Rubin

  DOI：10.1021/jo4011798

  日期：2013.8.2

  A highly chemo- and diastereoselective protocol toward amino-substituted donor acceptor cyclopropanes via the formal nucleophilic displacement in bromocyclopropanes is described. A wide range of N-nucleophiles, including carboxamides, sulfonamides, azoles, and anilines, can be efficiently employed in this transformation, providing expeditious access to stereochemically defined and densely functionalized cydopropylamine derivatives.