(S)-2-(adamantan-1-yl)-2-fluoroethanol | 862668-99-3

• 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: (S)-2-(adamantan-1-yl)-2-fluoroethanol
• 英文别名: (2S)-2-(1-adamantyl)-2-fluoroethanol
• CAS: 862668-99-3
• 化学式: C₁₂H₁₉FO
• 分子量: 198.281
• InChiKey: UCHBEFXRWHTQSD-LTMLNTECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 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：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-(adamantan-1-yl)-2-fluoroethanol 、 4-硝基苯甲酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-4-nitrobenzoic acid 2-(adamantan-1-yl)-2-fluoroethyl ester
  参考文献：
  名称：

  通过简单的催化方法对映选择性形成立体碳-氟中心。

  摘要：

  DOI：

  10.1002/anie.200500395
• 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 、 sodium tetrahydroborate 、 N-氟代双苯磺酰胺 作用下， 以 甲醇 为溶剂， 生成 (S)-2-(adamantan-1-yl)-2-fluoroethanol
  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.
• Enantioselective Formation of Stereogenic Carbon-Fluorine Centers by a Simple Catalytic Method
  作者：Mauro Marigo、Doris Fielenbach、Alan Braunton、Anne Kjærsgaard、Karl Anker Jørgensen

  DOI：10.1002/anie.200500395

  日期：2005.6.13