(2-brom cyclopropyl)(morpholin-4-yl)methanone | 1219811-06-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (2-brom cyclopropyl)(morpholin-4-yl)methanone
• 英文别名: (2-bromocyclopropyl)(morpholino)methanone；(2-Bromocyclopropyl)-morpholin-4-ylmethanone
• CAS: 1219811-06-9
• 化学式: C₈H₁₂BrNO₂
• 分子量: 234.093
• InChiKey: LSJRWTRQPKYFBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,6-二甲基苯酚 、 (2-brom cyclopropyl)(morpholin-4-yl)methanone 在 18-冠醚-6 、 potassium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以83%的产率得到((1RS,2RS)-2-(2,6-dimethylphenoxy)cyclopropyl)(4-morpholino)methanone
  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
• 作为产物：
  描述：

  (2,2-dibrom cyclopropyl)(morpholin-4-yl)methanone 在 异丙基溴化镁 、 水 、 氯化铵 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以86%的产率得到(2-brom cyclopropyl)(morpholin-4-yl)methanone
  参考文献：
  名称：

  Thermodynamic Control of Diastereoselectivity in the Formal Nucleophilic Substitution of Bromocyclopropanes

  摘要：

  A new, general, and chemoselective protocol for the formal nucleophilic substitution of 2-bromocyclopropylcarboxamides Is described. A wide range of alcohols and phenols can be employed as pronucleophiles in this transformation, providing expeditious access to trans-cyclopropanol ethers. A new mode of the selectivity control through a thermodynamic equilibrium is realized, alternative to the previously described steric and directing modes.

  DOI：

  10.1021/ol100187c

文献信息

• 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.
• 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。
• Thermodynamic Control of Diastereoselectivity in the Formal Nucleophilic Substitution of Bromocyclopropanes
  作者：Joseph E. Banning、Anthony R. Prosser、Michael Rubin

  DOI：10.1021/ol100187c

  日期：2010.4.2

  A new, general, and chemoselective protocol for the formal nucleophilic substitution of 2-bromocyclopropylcarboxamides Is described. A wide range of alcohols and phenols can be employed as pronucleophiles in this transformation, providing expeditious access to trans-cyclopropanol ethers. A new mode of the selectivity control through a thermodynamic equilibrium is realized, alternative to the previously described steric and directing modes.