(R)-2-chloro-3,3-dimethylbutan-1-ol

• 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: (R)-2-chloro-3,3-dimethylbutan-1-ol
• 英文别名: 2-chloro-3,3-dimethylbutan-1-ol；(2R)-chloro-3,3-dimethylbutan-1-ol；(2R)-2-chloro-3,3-dimethylbutan-1-ol
• 化学式: C₆H₁₃ClO
• 分子量: 136.622
• InChiKey: LELKLXCTOOXGLO-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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：
  1

反应信息

• 作为产物：
  描述：

  3,3-二甲基丁醛 在 sodium tetrahydroborate 、 N-氯代丁二酰亚胺 、 L-脯氨酰胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 (R)-2-chloro-3,3-dimethylbutan-1-ol
  参考文献：
  名称：

  醛的直接有机催化不对称α-氯化

  摘要：

  已经开发了醛的直接有机催化对映选择性 α-氯化。使用容易获得的催化剂如 l-脯氨酸酰胺和 (2R,5R)-二苯基吡咯烷，以 NCS 作为氯源，对一系列不同的醛进行反应。α-氯醛的产率高达 99%，ee 高达 95%。通过标准还原将 α-氯醛转化为相应的 α-氯醇（>90% 产率）并进一步转化为末端环氧化物和氨基醇，证明了醛的对映选择性 α-氯化的合成效用在不损失光学纯度的情况下获得。氧化 α-氯醛，然后酯化，得到光学活性的 α-氯酯，而没有损失光学纯度。

  DOI：

  10.1021/ja049231m

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。
• Organocatalytic asymmetric fluorination of α-chloroaldehydes involving kinetic resolution
  作者：Kazutaka Shibatomi、Takuya Okimi、Yoshiyuki Abe、Akira Narayama、Nami Nakamura、Seiji Iwasa

  DOI：10.3762/bjoc.10.30

  日期：——

  of the starting aldehydes was involved in this asymmetric fluorination. This paper describes the determination of the absolute stereochemistry of a resulting alpha-chloro-alpha-fluoroaldehyde. Some information about the substrate scope and a possible reaction mechanism are also described which shed more light on the nature of this asymmetric fluorination reaction.

  在先前的研究中表明，外消旋 α-氯醛与手性有机催化剂的对映选择性 α-氟化产生具有高对映选择性的相应 α-氯-α-氟醛。还揭示了起始醛的动力学拆分参与了这种不对称氟化。本文描述了所得 α-氯-α-氟醛的绝对立体化学的测定。还描述了一些关于底物范围和可能的反应机制的信息，这对这种不对称氟化反应的性质有更多的了解。
• Enantioselective α-Chlorination of Aldehydes with Recyclable Fluorous (S)-Pyrrolidine-Thiourea Bifunctional Organocatalyst
  作者：Chun Cai、Wei Zhang、Liang Wang、Dennis Curran

  DOI：10.1055/s-0029-1219198

  日期：2010.2

  A novel fluorous (S)-pyrrolidine-thiourea bifunctional organocatalyst is prepared. The catalyst shows good activity and enantioselectivity for direct α-chlorination of aldehydes using N-chlorosuccinimide (NCS) as the chlorine source. It can be recovered from the reaction mixture by fluorous solid-phase extraction with excellent purity for direct reuse.

  制备了一种新型的氟（S）-吡咯烷-硫脲双功能有机催化剂。该催化剂在使用 N-氯代琥珀酰亚胺 (NCS) 作为氯源直接 α-氯化醛时表现出良好的活性和对映选择性。它可以通过氟固相萃取从反应混合物中回收，纯度极佳，可直接重复使用。
• Nucleophilic Reactions between Cyclic 1,2-Sulfites and Chloride Ions.
  作者：Kirsten Nymann、Linda Jensen、John S. Svendsen、T. Anthonsen、Ryszard Gawinecki、Günter Häfelinger、Muhammed Nour Homsi、Frank K. H. Kuske、Monika Haugg、Nathalie Trabesinger-Rüf、Elmar G. Weinhold

  DOI：10.3891/acta.chem.scand.50-0832

  日期：——

  When cyclic 1,2-sulfites are ring opened by chloride ion, the chlorohydrins are formed with low regio and stereo-selectivity. The mechanisms involved in the process were investigated by measuring the stereochemical outcome of the reactions. The results showed that reversible inversion pathways (S(N)2 reactions) and a retention pathway (S(N)2i reaction) gave rise to the loss in ee in both the chlorohydrins and in the cyclic 1,2-sulfites.
• Catalytic Asymmetric Synthesis of Optically Active Alpha-Halo-Carbonyl Compounds
  申请人：Halland Nis

  公开号：US20070276142A1

  公开（公告）日：2007-11-29

  A process for the catalytic asymmetric synthesis of an optically active compound of the formula (1a) or (1b) wherein R is an organic group; X is halogen; R 1 and R 2 which may the same or different represents H, or an organic group or R 1 and R 2 may be bridged together forming part of a ring system; R and R 2 may be bridged together forming part of a ring system; with the provisio that R and R 1 are different and R 2 , 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.