(1S,2S)-2-氯环己烷-1-醇 | 931-13-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (1S,2S)-2-氯环己烷-1-醇
• 英文名称: cis-(1R,2S)-2-chlorocyclohexanol
• 英文别名: (1R,2S)-2-chloro-cyclohexanol；(1R,2S)-2-chlorocyclohexanol；cis-2-chloro-cyclohexanol；cis-α-Chlor-cyclohexanol；cis-2-Chlor-cyclohexanol-(1)；2-Chlorocyclohexanol, cis；(1R,2S)-2-chlorocyclohexan-1-ol
• CAS: 931-13-5；1561-86-0；6628-80-4；16536-58-6；64363-94-6；104265-20-5；116783-28-9；122210-63-3
• 化学式: C₆H₁₁ClO
• 分子量: 134.606
• InChiKey: NYEWDMNOXFGGDX-NTSWFWBYSA-N

物化性质

• 熔点：
  29 °C
• 沸点：
  88-90°C 20mm
• 密度：
  1.13 g/mL at 25 °C(lit.)
• 闪点：
  158 °F

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• 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

制备方法与用途

化学性质： 这是一种无色液体，相对密度为1.130，折光率为nD20 1.4880。

用途： 主要用于有机合成中间体，并用于合成低毒高效杀螨剂——克螨特。

生产方法： 环己烯与次氯酸溶液在15-20℃下激烈搅拌反应，直至用碘化钾和稀盐酸试验反应液不产生碘的颜色。随后加入第二份次氯酸溶液并重复上述反应操作和试验。当反应完成时，反应物会沉降出油层，并使用碘化钾检测应有少许过量的次氯酸存在。生成的2-氯环己醇可通过蒸馏方法分离出来。

反应信息

• 作为反应物：
  描述：

  (1S,2S)-2-氯环己烷-1-醇 、 甲氧基-三氟甲基苯 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Enzymatic preparation of (1S,2R)- and (1R,2S)-stereoisomers of 2-halocycloalkanols

  摘要：

  The stereoisomers of cis-2-halocycloalkanols were resolved by a kinetically controlled transesterification with vinyl acetate in the presence of lipases in organic media. High enantioselectivities (ee >98%) and good isolated yields were obtained for all substrates using the appropriate lipase. Burkholderia cepacia lipase was the most efficient enzyme for the resolution of these substrates. The enantiomeric purities of the compounds were defined by derivatization with Mosher's acid and the absolute configurations were determined by chemical correlation. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.11.011
• 作为产物：
  描述：

  2-氯环己酮 在 甲醇 、 sodium tetrahydroborate 、 Burkholderia cepacia Amano PS lipase 、 potassium carbonate 作用下， 以 甲醇 、 甲基叔丁基醚 为溶剂， 反应 16.0h， 生成 (1S,2S)-2-氯环己烷-1-醇
  参考文献：
  名称：

  Enzymatic preparation of (1S,2R)- and (1R,2S)-stereoisomers of 2-halocycloalkanols

  摘要：

  The stereoisomers of cis-2-halocycloalkanols were resolved by a kinetically controlled transesterification with vinyl acetate in the presence of lipases in organic media. High enantioselectivities (ee >98%) and good isolated yields were obtained for all substrates using the appropriate lipase. Burkholderia cepacia lipase was the most efficient enzyme for the resolution of these substrates. The enantiomeric purities of the compounds were defined by derivatization with Mosher's acid and the absolute configurations were determined by chemical correlation. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.11.011

文献信息

• Enantioselective Synthesis of Vicinal Halohydrins via Dynamic Kinetic Resolution
  作者：Abel Ros、Antonio Magriz、Hansjörg Dietrich、Rosario Fernández、Eleuterio Alvarez、José M. Lassaletta

  DOI：10.1021/ol052821k

  日期：2006.1.1

  [reaction: see text] Expanding the scope of enantioselective catalysis via DKR, transfer hydrogenation of a variety of cyclic alpha-halo ketones was accomplished using the Noyori/Ikariya (R,R)- or (S,S)-I catalysts and either HCO(2)H/Et(3)N or HCO(2)Na/n-Bu(4)NBr in H(2)O/CH(2)Cl(2) as the hydrogen sources. Good yields of vicinal bromo-, chloro-, and fluorohydrins with excellent de and ee levels were

  [反应：见正文]使用Noyori / Ikariya（R，R）-或（S，S）-I催化剂，通过DKR扩大了对映选择性催化的范围，转移了各种环状α-卤代酮的氢化反应HCO（2）H / Et（3）N或H（2）O / CH（2）Cl（2）中的HCO（2）Na / n-Bu（4）NBr作为氢源。在大多数情况下，只需简单调整反应条件，即可获得具有优良de和ee水平的邻位溴代，氯代和氟代醇的良好收率。
• Advanced Insights into Catalytic and Structural Features of the Zinc‐Dependent Alcohol Dehydrogenase from <i>Thauera aromatica</i>
  作者：Frances Stark、Christoph Loderer、Mark Petchey、Gideon Grogan、Marion B. Ansorge‐Schumacher

  DOI：10.1002/cbic.202200149

  日期：2022.8.3

  The zinc-dependent MDR−ADH (medium chain dehydrogenase/reductase−alcohol dehydrogenase) from Thauera aromatica has a unique substrate preference for sterically demanding α-substituted linear cyclic carbonyl compounds and a remarkable thermal, pH and solvent stability. Based on high-resolution structures from X-ray analysis, structural determinants for the enzyme's special features are introduced.

  来自Thauera 芳香族a的锌依赖性 MDR-ADH（中链脱氢酶/还原酶-醇脱氢酶）对空间要求高的 α-取代的线性环状羰基化合物具有独特的底物偏好，并且具有显着的热稳定性、pH 和溶剂稳定性。基于 X 射线分析的高分辨率结构，介绍了酶的特殊功能的结构决定因素。
• NARUSE, YUJI;ESAKI, TORU;YAMAMOTO, HISASHI, TETRAHEDRON, 44,(1988) N 15, C. 4747-4756
  作者：NARUSE, YUJI、ESAKI, TORU、YAMAMOTO, HISASHI

  DOI：——

  日期：——
• Enzymatic preparation of (1S,2R)- and (1R,2S)-stereoisomers of 2-halocycloalkanols
  作者：Olga O. Kolodiazhna、Anastasy O. Kolodiazhna、Oleg I. Kolodiazhnyi

  DOI：10.1016/j.tetasy.2012.11.011

  日期：2013.1

  The stereoisomers of cis-2-halocycloalkanols were resolved by a kinetically controlled transesterification with vinyl acetate in the presence of lipases in organic media. High enantioselectivities (ee >98%) and good isolated yields were obtained for all substrates using the appropriate lipase. Burkholderia cepacia lipase was the most efficient enzyme for the resolution of these substrates. The enantiomeric purities of the compounds were defined by derivatization with Mosher's acid and the absolute configurations were determined by chemical correlation. (C) 2012 Elsevier Ltd. All rights reserved.

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