(2R)-2-(1-adamantyl)-2-bromoethanol

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: (2R)-2-(1-adamantyl)-2-bromoethanol
• 化学式: C₁₂H₁₉BrO
• mdl: MFCD01838644
• 分子量: 259.186
• InChiKey: GOWAYBOLMKNUTJ-CRCJWISWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  adamantan-1-ylacetaldehyde 在 S-α,α-双(3,5-二三氟甲基苯基)脯氨醇三甲基硅醚 、 4,4-二溴-2,6-二叔丁基-2,5-CYLO己二烯ONE 、 苯甲酸 、 sodium tetrahydroborate 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 0.17h， 生成 (2S)-2-(1-adamantyl)-2-bromoethanol 、 (2R)-2-(1-adamantyl)-2-bromoethanol
  参考文献：
  名称：

  A General Organocatalyst for Direct α-Functionalization of Aldehydes:  Stereoselective C−C, C−N, C−F, C−Br, and C−S Bond-Forming Reactions. Scope and Mechanistic Insights

  摘要：

  The development of a general organocatalyst for the alpha-functionalization of aldehydes, via an enamine intermediate, is presented. Based on optically active alpha,alpha-diarylprolinol silyl ethers, the scope and applications of this catalyst for the stereogenic formation of C-C, C-N, C-F, C-Br, and C-S bonds are outlined. The reactions all proceed in good to high yields and with excellent enantioselectivities. Furthermore, we will present mechanistic insight into the reaction course applying nonlinear effect studies, kinetic resolution, and computational investigations leading to an understanding of the properties of the alpha,alpha-diarylprolinol silyl ether catalysts.

  DOI：

  10.1021/ja056120u

文献信息

• A General Organocatalyst for Direct α-Functionalization of Aldehydes:  Stereoselective C−C, C−N, C−F, C−Br, and C−S Bond-Forming Reactions. Scope and Mechanistic Insights
  作者：Johan Franzén、Mauro Marigo、Doris Fielenbach、Tobias C. Wabnitz、Anne Kjærsgaard、Karl Anker Jørgensen

  DOI：10.1021/ja056120u

  日期：2005.12.1

  The development of a general organocatalyst for the alpha-functionalization of aldehydes, via an enamine intermediate, is presented. Based on optically active alpha,alpha-diarylprolinol silyl ethers, the scope and applications of this catalyst for the stereogenic formation of C-C, C-N, C-F, C-Br, and C-S bonds are outlined. The reactions all proceed in good to high yields and with excellent enantioselectivities. Furthermore, we will present mechanistic insight into the reaction course applying nonlinear effect studies, kinetic resolution, and computational investigations leading to an understanding of the properties of the alpha,alpha-diarylprolinol silyl ether catalysts.