1,1,1-三氯-3,3,3-三氟-2-甲基丙烷-2-醇 | 145938-91-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1,1,1-三氯-3,3,3-三氟-2-甲基丙烷-2-醇
• 英文名称: 3,3,3-trifluoro-2-hydroxy-2-methyl-1,1,1-trichloropropane
• 英文别名: 2-Propanol, 1,1,1-trichloro-3,3,3-trifluoro-2-methyl-；1,1,1-trichloro-3,3,3-trifluoro-2-methylpropan-2-ol
• CAS: 145938-91-6
• 化学式: C₄H₄Cl₃F₃O
• 分子量: 231.429
• InChiKey: WUNCYUIIHPDUNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  11
• 可旋转键数：
  0
• 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：
  4

反应信息

• 作为反应物：
  描述：

  1,1,1-三氯-3,3,3-三氟-2-甲基丙烷-2-醇 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.33h， 以81%的产率得到2,2-Dichloro-3-methyl-3-trifluoromethyl-oxirane
  参考文献：
  名称：

  Trichloromethylation of fluoroketones

  摘要：

  The nucleophilic trichloromethylation of fluoroketones was carried out by the reductive addition of CCl4 in the presence of aluminum or by the reaction of trichloroacetic acid in HMPTA. The trichloromethylcarbinols obtained were used in the synthesis of perfluorinated tertiary alcohols and trifluoromethylated 1,1-dichlorooxiranes.

  DOI：

  10.1007/bf00869539
• 作为产物：
  描述：

  四氯化碳 、 1,1,1-三氟丙酮 在 氢化铝 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 以58%的产率得到1,1,1-三氯-3,3,3-三氟-2-甲基丙烷-2-醇
  参考文献：
  名称：

  Trichloromethylation of fluoroketones

  摘要：

  The nucleophilic trichloromethylation of fluoroketones was carried out by the reductive addition of CCl4 in the presence of aluminum or by the reaction of trichloroacetic acid in HMPTA. The trichloromethylcarbinols obtained were used in the synthesis of perfluorinated tertiary alcohols and trifluoromethylated 1,1-dichlorooxiranes.

  DOI：

  10.1007/bf00869539

文献信息

• Synthetic application of 3,3-dichloro-1,1,1-trifluoroacetone (DCTFA) and 3,3,3-trichloro-1,1,1-trifluoroacetone (TCTFA) for trifluorolactic acid derivatives
  作者：Akihiro Ishii、Masatomi Kanai、Manabu Yasumoto、Kenjin Inomiya、Yokusu Kuriyama、Yutaka Katsuhara

  DOI：10.1016/j.jfluchem.2003.11.030

  日期：2004.4

  the other hand, α-substituted trifluorolactic acid derivatives, such as α-methyltrifluorolactic acid and Mosher’s acid, were obtained by addition reaction between TCTFA and carbon nucleophiles, followed by subsequent transformation of trichloromethyl group.

  描述了3,3-二氯-1,1,1-三氟丙酮（DCTFA）和3,3,3-三氯-1,1,1-三氟丙酮（TCTFA）在工业上重要的三氟乳酸衍生物的合成应用。通过在碱性条件下水解DCTFA获得三氟乳酸。另一方面，通过TCTFA与碳亲核试剂之间的加成反应，随后进行三氯甲基的转化，获得了α-取代的三氟乳酸衍生物，例如α-甲基三氟乳酸和莫舍尔酸。
• JP2005/194227
  申请人：——

  公开号：——

  公开（公告）日：——
• Chirality-dependent sublimation of -(trifluoromethyl)-lactic acid: Relative vapor pressures of racemic, eutectic, and enantiomerically pure forms, and vibrational spectroscopy of isolated (S,S) and (S,R) dimers
  作者：Merwe Albrecht、Vadim A. Soloshonok、Lena Schrader、Manabu Yasumoto、Martin A. Suhm

  DOI：10.1016/j.jfluchem.2009.11.015

  日期：2010.4

  A mass-spectrometric determination of the sublimation pressure diagram of alpha-(trifluoromethyl)-lactic acid as a function of its enantiomeric composition at 293 K shows that the racemic crystals have a 38 +/- 15% higher volatility than the enantiomerically pure crystals and the sublimation eutectic has a 55 +/- 10% higher vapor pressure. These data indicate a possibility for thermodynamically controlled enantiomeric enrichment of the residual material via sublimation of samples of higher than 35 +/- 10% ee. The vibrational spectroscopy of isolated (S,S) and (S,R) dimers in supersonic jets shows that chirality recognition effects are restricted to larger clusters. This is a consequence of the rigid planar carboxylic acid binding motif. (C) 2009 Elsevier B.V. All rights reserved.