α-(trichloromethyl)cyclohexanemethanol | 57741-12-5

• 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: α-(trichloromethyl)cyclohexanemethanol
• 英文别名: 1,1,1-trichloro-2-cyclohexylethan-2-ol；2,2,2-trichloro-1-cyclohexyl-ethanol；cyclohexyl (trichloromethyl)carbinol；2,2,2-trichloro-1-cyclohexylethanol；(+/-)-(2.2.2-Trichlor-1-hydroxy-aethyl)-cyclohexan；2,2,2-Trichlor-1-cyclohexyl-aethanol；1-Cyclohexyl-2,2,2-trichloroethanol
• CAS: 57741-12-5
• 化学式: C₈H₁₃Cl₃O
• 分子量: 231.55
• InChiKey: YNQHTZHOPABBGP-UHFFFAOYSA-N

物化性质

• 沸点：
  119-121 °C(Press: 15 Torr)
• 密度：
  1.2839 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  12
• 可旋转键数：
  1
• 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：

  α-(trichloromethyl)cyclohexanemethanol 在 锂硼氢 、 sodium hydroxide 作用下， 以 异丙醇 为溶剂， 以86%的产率得到2-环己基乙醇
  参考文献：
  名称：

  伯醇的单碳认证和涉及 Jocic 型反应的醛的还原认证

  摘要：

  （三氯甲基）甲醇在一次操作中由醇或醛形成，可在涉及 LiBH4 的 Jocic 型反应中转化为伯醇。最终结果是方便的两步，伯醇的单碳同源或醛的还原性单碳同源，具有广泛的底物范围。该方法是步骤经济的，它很好地补充了已建立的单碳同源策略。

  DOI：

  10.1002/ejoc.201501089
• 作为产物：
  描述：

  三甲基(2,2,2-三氯-1-环己基乙氧基)硅烷 在 四丁基氟化铵 、 溶剂黄146 、 potassium carbonate 作用下， 以 四氢呋喃 、 2-甲基四氢呋喃 、 水 为溶剂， 反应 0.67h， 以94%的产率得到α-(trichloromethyl)cyclohexanemethanol
  参考文献：
  名称：

  One-Pot in Situ Formation and Reaction of Trimethyl(trichloromethyl)silane: Application to the Synthesis of 2,2,2-Trichloromethylcarbinols

  摘要：

  2,2,2-Trichloromethylcarbinols are 1 are valuable synthetic intermediates with a multitude of uses. A scalable procedure for the synthesis of TMS-protected-2,2,2-trichloromethylcarbinols and 2,2,2-trichloromethylcarbinols 1 was developed that employs the in situ generation and reaction of trimethyl(trichloromethyl)silane (CCl3-TMS). The procedure avoids the exposure of the carbonyl compounds to the strongly basic conditions typically used for this transformation and also avoids isolation of the difficult-to-handle CCl3-TMS. This procedure was applied to diastereoselective trichloromethyl additions to 2-substituted 4-piperidinones and to reactions with a variety of structurally diverse aldehydes and ketones.

  DOI：

  10.1021/jo3001063

文献信息

• Trichloromethyl ketones: asymmetric transfer hydrogenation and subsequent Jocic-type reactions with amines
  作者：Michael S. Perryman、Matthew E. Harris、Jade L. Foster、Anushka Joshi、Guy J. Clarkson、David J. Fox

  DOI：10.1039/c3cc46070c

  日期：——

  Amino-amides are important pharmaceutical building-blocks. The enantioselective reduction of trichloromethyl ketones using ruthenium transfer hydrogenation catalysts is reported. The products react in a range of Jocic-type reactions to give enantiomerically enriched amino-amides.

  氨基酰胺是重要的药物构建模块。报道了使用钌转移氢化催化剂对三氯甲基酮进行的不对称还原反应。产物在多种Jocic型反应中得到转化，产生手性富集的氨基酰胺。
• One-Pot Synthesis of Trichloromethyl Carbinols from Primary Alcohols
  作者：Manoj K. Gupta、Zhexi Li、Timothy S. Snowden

  DOI：10.1021/jo300725v

  日期：2012.5.18

  Versatile trichloromethyl carbinols can be prepared in one pot from primary alcohols by treatment with Dess–Martin periodinane (DMP) in CHCl3 followed by introduction of commercially available 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD). A modification of the method was used to convert chiral primary alcohol (R)-(−)-2,2-dimethyl-1,3-dioxolane-4-methanol to the corresponding trichloromethyl carbinol with

  可以通过用Dess-Martin高碘烷（DMP）在CHCl 3中处理，然后引入市售的1,5,7-三氮杂双环[4.4.0] dec-5-ene（TBD ），在一锅中由伯醇制备多功能的三氯甲基甲醇。）。方法的一种改进是将手性伯醇（R）-（-）-2,2-二甲基-1,3-二氧戊环-4-甲醇转化为相应的具有完全立体化学保真度的三氯甲基甲醇，尽管反应物通过碱敏感的醛中间体。
• General and Practical Conversion of Aldehydes to Homologated Carboxylic Acids
  作者：Lauren R. Cafiero、Timothy S. Snowden

  DOI：10.1021/ol8016484

  日期：2008.9.1

  under basic conditions affords homologated carboxylic acids in high yields. This operationally simple procedure provides a practical, efficient alternative to other homologation protocols. The approach is compatible with sensitive aldehydes including enals and enolizable aldehydes. It also offers convenient access to alpha-monodeuterated carboxylic acids.

  在碱性条件下，醛与三氯甲基甲烷，然后与硼氢化钠或苯基硒基（三乙基）硼酸钠反应，可以高收率得到同系羧酸。该操作简单的过程为其他认证协议提供了一种实用，有效的替代方法。该方法与敏感的醛兼容，包括烯醛和可烯化的醛。它还提供了方便的获取α-单十二烷基羧酸的途径。
• A new and practical synthesis of vinyl dichlorides via a non-Wittig-type approach
  作者：Zhe Wang、Silvio Campagna、Guoyou Xu、Michael E Pierce、Joseph M Fortunak、Pat N Confalone

  DOI：10.1016/s0040-4039(00)00547-5

  日期：2000.5

  A practical approach for the conversion of aldehydes to vinyl dichlorides has been developed. These are three-step, one-pot reactions involving the formation of trichlorocarbinol by treatment of aldehydes with trichloroacetic acid and sodium trichloroacetate followed by in situ protection and elimination reactions to form the desired vinyl dichlorides in 85 to 95% yields.

  已经开发了一种将醛转化为二氯乙烯的实用方法。这些是三步一锅法反应，包括通过用三氯乙酸和三氯乙酸钠处理醛来形成三氯甲醇，然后进行原位保护和消除反应，以85至95％的收率形成所需的二氯乙烯。
• Two effective procedures for the synthesis of trichloromethyl ketones, useful precursors of chiral α-amino and α-hydroxy acids
  作者：E.J. Corey、John O. Link、Yang Shao

  DOI：10.1016/s0040-4039(00)92656-x

  日期：1992.6

  Trichloroacetic acid can been converted to trichloromethyl ketones in good yield by two practical new procedures, one involving the catalyzed reaction of trichloroacetic acid with aldehydes at 23 °C followed by oxidation and the other utilizing the coupling of organozinc intermediates with trichloroacetyl chloride

  可以通过两种实用的新方法将三氯乙酸以高收率转化为三氯甲基酮，一种涉及三氯乙酸与醛在23°C的催化反应，然后进行氧化，另一种利用有机锌中间体与三氯乙酰氯的偶联