(1R*,2S*)-1-bromo-N-(tert-butyl)-2-methyl-2-phenylcyclopropanecarboxamide

• 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: (1R*,2S*)-1-bromo-N-(tert-butyl)-2-methyl-2-phenylcyclopropanecarboxamide
• 英文别名: (1R,2S)-1-bromo-N-tert-butyl-2-methyl-2-phenylcyclopropane-1-carboxamide
• 化学式: C₁₅H₂₀BrNO
• 分子量: 310.234
• InChiKey: SCDANMYQPMLTHF-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  乙二醇甲醚 、 (1R*,2S*)-1-bromo-N-(tert-butyl)-2-methyl-2-phenylcyclopropanecarboxamide 在 18-冠醚-6 、 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 12.02h， 以79%的产率得到(1R*,2R*,3S*)-N-(tert-butyl)-3-(2-methoxyethoxy)-2-methyl-2-phenylcyclopropanecarboxamide
  参考文献：
  名称：

  Dual Control of the Selectivity in the Formal Nucleophilic Substitution of Bromocyclopropanes en Route to Densely Functionalized, Chirally Rich Cyclopropyl Derivatives

  摘要：

  Densely substituted cyclopropanol and cyclopropylazole derivatives with three stereogenic carbons in the small cycle are obtained via a highly diastereoselective formal nucleophilic substitution of bromocyclopropanes. The chiral center at C-2 in bromocyclopropane dictates the configuration of the other two stereocenters that are successively installed via a sterically controlled addition of a nucleophile, followed by a thermodynamically driven epimerization of the resulting enolate intermediate.

  DOI：

  10.1021/ol4027792
• 作为产物：
  描述：

  (2,2-dibromo-1-methylcyclopropyl)benzene 在 正丁基锂 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 4.83h， 生成 (1R*,2S*)-1-bromo-N-(tert-butyl)-2-methyl-2-phenylcyclopropanecarboxamide
  参考文献：
  名称：

  Dual Control of the Selectivity in the Formal Nucleophilic Substitution of Bromocyclopropanes en Route to Densely Functionalized, Chirally Rich Cyclopropyl Derivatives

  摘要：

  Densely substituted cyclopropanol and cyclopropylazole derivatives with three stereogenic carbons in the small cycle are obtained via a highly diastereoselective formal nucleophilic substitution of bromocyclopropanes. The chiral center at C-2 in bromocyclopropane dictates the configuration of the other two stereocenters that are successively installed via a sterically controlled addition of a nucleophile, followed by a thermodynamically driven epimerization of the resulting enolate intermediate.

  DOI：

  10.1021/ol4027792

文献信息

• Dual Control of the Selectivity in the Formal Nucleophilic Substitution of Bromocyclopropanes en Route to Densely Functionalized, Chirally Rich Cyclopropyl Derivatives
  作者：Pavel Ryabchuk、Andrew Edwards、Nikolay Gerasimchuk、Marina Rubina、Michael Rubin

  DOI：10.1021/ol4027792

  日期：2013.12.6

  Densely substituted cyclopropanol and cyclopropylazole derivatives with three stereogenic carbons in the small cycle are obtained via a highly diastereoselective formal nucleophilic substitution of bromocyclopropanes. The chiral center at C-2 in bromocyclopropane dictates the configuration of the other two stereocenters that are successively installed via a sterically controlled addition of a nucleophile, followed by a thermodynamically driven epimerization of the resulting enolate intermediate.