(S)-2-fluorocyclohexylacetaldehyde

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氟化物
• 英文名称: (S)-2-fluorocyclohexylacetaldehyde
• 英文别名: (2S)-2-cyclohexyl-2-fluoroacetaldehyde
• 化学式: C₈H₁₃FO
• 分子量: 144.189
• InChiKey: ODIUBOAOVNDAMC-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-fluorocyclohexylacetaldehyde 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 (S)-2-cyclohexyl-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
• 作为产物：
  描述：

  环己基乙醛 在 chiral 2-[diaryl(trimethylsilanyloxy)methyl]pyrrolidine 、 N-氟代双苯磺酰胺 作用下， 以 various solvent(s) 为溶剂， 反应 5.17h， 生成 (S)-2-fluorocyclohexylacetaldehyde
  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

文献信息

• Enantioselective alpha-fluorination of aldehydes using chiral organic catalysts
  申请人：MacMillan W.C. David

  公开号：US20060189830A1

  公开（公告）日：2006-08-24

  Nonmetallic, chiral organic catalysts are used to catalyze enantioselective fluorination of enolizable aldehydes. Reaction systems composed of an enolizable aldehyde, an electrophilic fluorination reagent, and a nonmetallic chiral catalyst in the form of an imidazolidinone salt are also provided.

  非金属手性有机催化剂被用于催化不对称选择性氟化烯醇醛。由烯醇醛、亲电性氟化试剂和非金属手性催化剂（以咪唑啉酮盐形式）组成的反应体系也被提供。
• 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
• Rapid, General Access to Chiral β-Fluoroamines and β,β-Difluoroamines via Organocatalysis
  作者：Olugbeminiyi O. Fadeyi、Craig W. Lindsley

  DOI：10.1021/ol802930q

  日期：2009.2.19

  A rapid, general route to enantiopure beta-fluoroamines and beta,beta-difluoroamines has been developed employing organocatalysis in both a two-pot and a one-pot procedure. Both chemical yields (64-82%) and enantioselectivity (94-98% ee) were excellent and represent a significant improvement in the art of preparing chemically diverse beta-fluoroamines from readily available precursors.