2-chloro-1-cyclohexylethanol | 90202-27-0

• 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: 2-chloro-1-cyclohexylethanol
• 英文别名: 2-Chloro-1-cyclohexylethan-1-ol
• CAS: 90202-27-0
• 化学式: C₈H₁₅ClO
• 分子量: 162.66
• InChiKey: AGWIKTWYCHQYTC-UHFFFAOYSA-N

物化性质

• 沸点：
  83-86 °C(Press: 3.3 Torr)
• 密度：
  1.077±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  10
• 可旋转键数：
  2
• 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

反应信息

• 作为反应物：
  描述：

  2-chloro-1-cyclohexylethanol 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 2-环己基环氧乙烷
  参考文献：
  名称：

  Dynamic Kinetic Resolution of Racemic β-Haloalcohols: Direct Access to Enantioenriched Epoxides

  摘要：

  The direct chemo-enzymatic DKR of racemic beta-haloalcohols is reported, yielding the corresponding optically active epoxides in a single step. The mutant haloalcohol dehalogenase HheC Cys153Ser Trp249Phe is used for the asymmetric ring closure, whereas racemization of the remaining enantiomer of the haloalcohol is achieved using the new iridacycle 3, one of the most effective racemization catalysts to date for beta-haloalcohols.

  DOI：

  10.1021/ja805128x
• 作为产物：
  描述：

  2-chloro-1-cyclohexyl-1-ethanone 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 以68 %的产率得到2-chloro-1-cyclohexylethanol
  参考文献：
  名称：

  结合金和氧化还原酶催化获得有价值的富含对映体的脂肪族 β-氯醇

  摘要：

  富含对映体的 β-氯醇的合成因其作为有机合成中的构建单元的相关性而极具吸引力。然而，由于难以获得 α-氯酮前体，因此接近脂肪族衍生物特别具有挑战性。在此，我们提出了一种直接且可扩展的方法，通过水合-生物还原级联以并发方式结合金 ( I ) 和氧化还原酶催化。总共获得了九种带有不同官能团的脂肪族 β-氯代醇，具有非常高的产率 (63–88%) 和立体选择性 (>99% ee)。

  DOI：

  10.1039/d2ob01953a

文献信息

• A New Entry of Highly Selective and Nucleophilic BrH ₂ C‐ and ClH ₂ C‐Titanium Complexes for Carbonyl Coupling
  作者：Tu Hsin Yan、Bakthavachalam Ananthan、Su Haur Chang

  DOI：10.1002/ejoc.201801438

  日期：2019.1.31

  carbinols is presented. High chemoselectivity is illustrated by the TiCl4‐Mg‐promoted selective coupling of CH2Br2 or CH2Cl2 with an aldehyde in the presence of ketone and selective transfer of CH2Br or CH2Cl to saturated carbonyl moiety. This protocol is also suitable for sterically hindered and enolizable carbonyl compounds.

  提出了一种用于构建溴甲基或氯甲基甲醇的有效方法。高化学选择性通过的TiCl所示4 CH的-Mg促进的选择性耦合2溴2或CH 2氯2与酮和CH的选择性转移的存在下用醛2 Br或CH 2 CI至饱和羰基部分。该方案也适用于空间受阻和可烯醇化的羰基化合物。
• Efficient synthesis of chlorohydrins using ClCH2MgCl·LiCl
  作者：Rodolfo H.V. Nishimura、Fabiano T. Toledo、João L.C. Lopes、Giuliano C. Clososki

  DOI：10.1016/j.tetlet.2012.10.132

  日期：2013.1

  The mixed lithium-magnesium carbenoid ClCH2MgCl center dot LiCl was easily generated in THF through the reaction of chloroiodomethane with i-PrMgCl-LiCl at -78 degrees C. This reagent reacts well with a number of aldehydes to give the corresponding chlorohydrins in good yields. (C) 2012 Elsevier Ltd. All rights reserved.
• Empirical method for predicting enantioselectivity in catalytic reactions: demonstration with lipase and oxazaborolidine
  作者：Tadashi Ema、Norichika Ura、Masataka Yoshii、Toshinobu Korenaga、Takashi Sakai

  DOI：10.1016/j.tet.2009.09.058

  日期：2009.11

  We derived a novel equation capable of predicting the degree of enantioselectivity in a catalytic reaction without any knowledge of the reaction mechanism and/or the transition-state structure. and tested the validity of this equation by changing substrates systematically in the lipase or oxazaborolidine-catalyzed reactions A good correlation was observed between the predicted and observed E values, and the stereochemistry of the products Could be predicted correctly in most cases (28 out of 30) (C) 2009 Elsevier Ltd All rights reserved
• Aminophenylethanols and Related Compounds
  作者：Seymour L. Shapiro、Harold Soloway、Louis Freedman

  DOI：10.1021/ja01555a042

  日期：1958.11
• PROCESS FOR PREPARING DIVINYLARENE DIOXIDES
  申请人：Ripplinger Eric B.

  公开号：US20130123521A1

  公开（公告）日：2013-05-16

  A process for preparing a divinylarene dioxide including (a) reacting at least one divinylarene with hypochlorous acid to form a chlorohydrin; and (b) treating the chlorohydrin formed in step (a) with at least one base, under conditions to form a divinylarene dioxide product.