(S)-α-cyano-α-fluoro-p-tolylacetyl chloride | 677300-31-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-α-cyano-α-fluoro-p-tolylacetyl chloride
• 英文别名: (2S)-2-cyano-2-fluoro-2-(4-methylphenyl)acetyl chloride
• CAS: 677300-31-1
• 化学式: C₁₀H₇ClFNO
• 分子量: 211.623
• InChiKey: LJECHHODJUJDHI-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-(+)-1-苯基乙醇 、 (S)-α-cyano-α-fluoro-p-tolylacetyl chloride 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  通过IR确认溶液中CFTA酯的优选构象：手性醇立体化学分配的高度可靠的标准。

  摘要：

  通过检查红外光谱首次首次直接确认了衍生自溶液中的手性仲醇和手性衍生剂的非对映体酯的优选构象，这对于可靠地基于NMR的醇绝对立体化学分配至关重要CFTA酯的光谱。

  DOI：

  10.1039/b926793j
• 作为产物：
  描述：

  ethyl 2-cyano-2-(p-tolyl)acetate 在 吡啶 、 lithium hydroxide 、 草酰氯 、 sodium hydride 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 11.41h， 生成 (S)-α-cyano-α-fluoro-p-tolylacetyl chloride
  参考文献：
  名称：

  通过1H NMR光谱测定手性仲醇绝对构型的非常可靠的方法。

  摘要：

  令人惊奇的是，CFTA酯的稳定的平面上构象异构体使我们开发出一种新的且非常可靠的方法，用于分配具有最小结构差异的仲醇（例如手性二氢苯酚和α-单十二烷基苄醇）的绝对构型。

  DOI：

  10.1021/ol0479489

文献信息

• The CFTA Method: A Reliable Procedure for the Determination of the Absolute Configuration of Chiral Primary Amines by1H NMR Spectroscopic Analysis
  作者：Yoshio Takeuchi、Masaru Segawa、Hidehito Fujisawa、Kenji Omata、Siegfried N. Lodwig、Clifford J. Unkefer

  DOI：10.1002/anie.200600157

  日期：2006.7.10
• Reliable assignment of absolute configuration of chiral amines based on the analysis of 1H NMR spectra of their CFTA amide diastereomers
  作者：Tomoya Fujiwara、Masaru Segawa、Hidehito Fujisawa、Taiki Murai、Tamiko Takahashi、Kenji Omata、Kuninobu Kabuto、Siegfried N. Lodwig、Clifford J. Unkefer、Yoshio Takeuchi

  DOI：10.1016/j.tetasy.2008.03.003

  日期：2008.4

  Applications of the CFTA method, a new and reliable procedure for the determination of the absolute configuration of chiral primary amines, are described in detail. In addition to the very high reactivity of CFTA chloride, the stable anti-periplanar conformers of CFTA amides, associated with the chiral structure of fluorine atom on a stereogenic center, are the key factors that make the technique of using H-1 NMR analysis of the CFTA diastereomers very reliable. In particular, this method is useful for the determination of the absolute stereochemistry of isotopically multi-labeled amino acid derivatives. (C) 2008 Elsevier Ltd. All rights reserved.
• An efficient procedure for the resolution of α-cyano-α-fluoro-p-tolylacetic acid (CFTA) via the diastereomeric N-carbobenzyloxy-cis-1-amino-2-indanol esters
  作者：Tomoya Fujiwara、Masaki Sasaki、Kenji Omata、Chizuko Kabuto、Kuninobu Kabuto、Yoshio Takeuchi

  DOI：10.1016/j.tetasy.2003.12.024

  日期：2004.2

  Development of a new, efficient resolution method of alpha-cyano-alpha-fluoro-p-tolylacetic acid (CFTA) 2a has been successfully achieved, which has been troublesome to obtain by conventional methods, in spite of its outstanding ability as an NMR chiral derivatizing agent. Fractional recrystallization of a mixture of the diastereomeric CFTA esters prepared from racemic CFTA chloride and (1R,2S)-N-carbobenzyloxy-cis-1-amino-2-indanol (-)-B afforded the less-soluble diastereomer, which was hydrolyzed to give (S)-2a. It has also been demonstrated that optically active N-acetyl-cis-1-amino-2-indanol is effective for the chromatographic resolution of alpha-arylacetic acids including ibuprofen and naproxen. (C) 2003 Elsevier Ltd. All rights reserved.
• A Very Reliable Method for Determination of Absolute Configuration of Chiral Secondary Alcohols by ¹H NMR Spectroscopy
  作者：Yoshio Takeuchi、Hidehito Fujisawa、Ryoji Noyori

  DOI：10.1021/ol0479489

  日期：2004.11.1

  Surprisingly stable synperiplanar conformers of CFTA esters have led us to develop a new and very reliable method for assigning absolute configurations of even secondary alcohols having minimal structural differences, such as chiral benzhydrols and alpha-monodeuterated benzyl alcohols.

  令人惊奇的是，CFTA酯的稳定的平面上构象异构体使我们开发出一种新的且非常可靠的方法，用于分配具有最小结构差异的仲醇（例如手性二氢苯酚和α-单十二烷基苄醇）的绝对构型。
• Confirmation by IR of the preferred conformations of CFTA esters in solution: a highly reliable criterion for the stereochemistry assignment of chiral alcohols
  作者：Kenji Omata、Kohsuke Kotani、Kuninobu Kabuto、Tomoya Fujiwara、Yoshio Takeuchi

  DOI：10.1039/b926793j

  日期：——

  Direct confirmation of the preferred conformation of diastereomeric esters derived from a chiral secondary alcohol and a chiral derivatizing agent in solution, which is crucial for reliable NMR-based assignment of absolute stereochemistry of the alcohol, has been attained for the first time by examination of IR spectra of the CFTA esters.

  通过检查红外光谱首次首次直接确认了衍生自溶液中的手性仲醇和手性衍生剂的非对映体酯的优选构象，这对于可靠地基于NMR的醇绝对立体化学分配至关重要CFTA酯的光谱。