(2S)-2-fluoro-3,3-dimethylbutan-1-ol | 141022-94-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S)-2-fluoro-3,3-dimethylbutan-1-ol
• CAS: 141022-94-8
• 化学式: C₆H₁₃FO
• 分子量: 120.167
• InChiKey: BIXPLUJYBHAXHD-RXMQYKEDSA-N

物化性质

• 沸点：
  144.5±10.0 °C(Predicted)
• 密度：
  0.917±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• 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

• 作为产物：
  描述：

  3,3-二甲基丁醛 在 S-α,α-双(3,5-二三氟甲基苯基)脯氨醇三甲基硅醚 、 N-氟代双苯磺酰胺 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 (2S)-2-fluoro-3,3-dimethylbutan-1-ol
  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

• [EN] CATALYTIC ASYMMETRIC SYNTHESIS OF OPTICALLY ACTIVE alpha-HALO-CARBONYL COMPOUNDS<br/>[FR] SYNTHESE ASYMETRIQUE CATALYTIQUE DE COMPOSES DE DOLLAR G(A)-HALO-CARBONYLE OPTIQUEMENT ACTIFS
  申请人：HALLAND NIS

  公开号：WO2005080298A1

  公开（公告）日：2005-09-01

  A process for the catalytic asymmetric synthesis of an optically active compound of the formula (la) or (lb): wherein R is an organic group; X is halogen; Rl and R2which may the same or different represents H, or an organic group or Rl and R2 may be bridged together forming part of a ring system; R and R2 may be bridged together forming part of a ring system; with the provisio that R and Rl are different and R2, when different from H, is attached though a carbon-carbon bond, comprising the step of reacting a compound of the formula (2): with a halogenation agent in the presence of a catalytic amount of a chiral nitrogen containing organic compound.

  一种用于催化不对称合成光学活性化合物的方法，其化学式为(la)或(lb)：其中R是有机基团；X是卤素；R1和R2可以相同也可以不同，分别代表H，或者是有机基团，或者R1和R2可以通过形成环系统的桥连接在一起；R和R2可以通过形成环系统的桥连接在一起；在R和R1不同且R2与H不同时通过碳-碳键连接时，包括以下步骤：将化合物(2)与卤化试剂在含有含有手性氮的有机化合物的催化剂量的情况下反应。
• Diastereoselective fluorination of chiral imide enolates using n-fluoro-o-benzenedisulfonimide (nfobs)
  作者：Franklin A. Davis、Wei Han

  DOI：10.1016/s0040-4039(00)91883-5

  日期：1992.2

  α-Fluoro acids (78–90% ee) and β-fluoro alcohols (89–>95%ee) of well defined stereochemistry are prepared via the diastereoselective fluorination of chiral imide enolates with NFOBS (3).

  定义明确的立体化学的α-氟酸（78-90％ee）和β-氟醇（89-> 95％ee）是通过使用NFOBS对手性酰亚胺烯酸酯进行非对映选择性氟化而制得的（3）。