(2R,3S)-3-氯丁烷-2-醇 | 10325-41-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 中文名称: (2R,3S)-3-氯丁烷-2-醇
• 英文名称: erythro-3-chloro-2-butanol
• 英文别名: erythro-3-chlorobutan-2-ol；(2RS,3SR)-3-chloro-butan-2-ol；(+/-)-erythro-3-chloro-butanol-(2)；(+/-)-erythro-3-Chlor-butanol-(2)；Inaktives erythro-3-Chlor-butanol-(2)；(R*,S*)-3-chloro-2-butanol；2-Butanol, 3-chloro-, (R*,S*)-；(2R,3S)-3-chlorobutan-2-ol
• CAS: 10325-41-4
• 化学式: C₄H₉ClO
• 分子量: 108.568
• InChiKey: XKEHIUIIEXXHJX-IUYQGCFVSA-N

物化性质

• 沸点：
  135.4 °C(Press: 748 Torr)
• 密度：
  1.0610 g/cm3(Temp: 25 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  6
• 可旋转键数：
  1
• 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

• 作为反应物：
  描述：

  (2R,3S)-3-氯丁烷-2-醇 在 氯化亚砜 作用下， 生成 meso-2,3-dichlorobutane
  参考文献：
  名称：

  Lucas; Gould, Journal of the American Chemical Society, 1941, vol. 63, p. 2548

  摘要：

  DOI：
• 作为产物：
  描述：

  反-2-丁烯 在 次氯酸 作用下， 生成 (2R,3S)-3-氯丁烷-2-醇
  参考文献：
  名称：

  Neighboring group participation in free-radical reactions of halohydrins and hydroxysulfides

  摘要：

  DOI：

  10.1021/jo00804a029

文献信息

• The pseudo-enzymatic action of tri-o-thymotide clathrates applied to the determination of the absolute configuration of four halohydrins
  作者：Raymond Gerdil、Giacomo Barchietto

  DOI：10.1016/s0040-4039(00)70648-4

  日期：——

  The heterogeneous reactions of gaseous HCl and HBr, as external agents, with trans-2,3-dimethyloxirane and 2,2,3-trimethyloxirane as guest molecules in tri-o-thymotide clathrates are shown to allow the ready determination of the absolute configuration of the end-products owing to highly specific host-reactant interactions.

  显示出气态HCl和HBr作为外在试剂，与反式-2,3-二甲基环氧乙烷和2,2,3-三甲基环氧乙烷作为客体分子在三邻胸腺嘧啶笼形包合物中的异质反应，可以随时测定其绝对构型由于高度特定的宿主反应物相互作用，导致最终产品的数量减少。
• Chemistry of nitrosoureas. Decomposition of 1,3-bis(threo-3-chloro-2-butyl)-1-nitrosourea and 1,3-bis(erythro-3-chloro-2-butyl)-1-nitrosourea
  作者：Robert B. Brundrett、Michael Colvin

  DOI：10.1021/jo00442a020

  日期：1977.10
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: B: B-Verb.9, 1.4.3.3, page 41 - 44
  作者：

  DOI：——

  日期：——
• Demonstration of a Phosphazirconocene as a Catalyst for the Ring Opening of Epoxides with TMSCl
  作者：Li-Sheng Wang、T. Keith Hollis

  DOI：10.1021/ol034816r

  日期：2003.7.1

  [GRAPHIC]In this study, it was demonstrated for the first time that a phosphazirconocene catalyzes the ring opening of epoxides with TMSCI. This reactivity leads to a facile preparation of chlorohydrins. The late transition metal Fe analogue was found to catalyze the reaction at rates and stereoselectivity comparable to those of the Zr complex.
• Synthesis of Oxochromium(VI) Alkoxides via Epoxide Cleavage. Structure, Reactivity, and Mechanism
  作者：Christian Limberg、Tobias Wistuba

  DOI：10.1021/jo982357f

  日期：1999.8.1

  In an NMR spectroscopic study the cleavage of epoxides [ethylene, propylene, and cis/trans-butylene oxide] by chromyl chloride giving access to oxochromium(VI) alkoxides was shown to proceed via a bimolecular rate-determining step where two molecules of a complex CrO2Cl2... epoxide collide. Subsequently one Cl ligand at the first Cr center attacks the backside of an epoxide molecule complexed at the Cr center of a second CrO2Cl2... epoxide molecule and vice versa. The traits-opening of the epoxides was proved by determining the configuration of the chlorohydrins resulting from hydrolysis of the corresponding alkoxide products in the cases of cis- and trans-butylene oxide. The NMR data provide evidence that each oxochromium(VI) alkoxide adopts one preferred conformation in solution although DFT calculations did not indicate any special stabilizing effects. The product formation was rationalized by DFT calculations concerning the thermodynamics of the reactions.