2,2,2-三氯-1-氰基-1-苯基乙醇 | 86797-12-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2,2,2-三氯-1-氰基-1-苯基乙醇
• 英文名称: 2,2,2-trichloro-1-cyano-1-phenylethanol
• 英文别名: 3,3,3-Trichloro-2-hydroxy-2-phenylpropanenitrile
• CAS: 86797-12-8；86797-13-9；113815-86-4
• 化学式: C₉H₆Cl₃NO
• 分子量: 250.512
• InChiKey: RZTOXQBFEVOILN-UHFFFAOYSA-N

物化性质

• 沸点：
  340.5±9.0 °C(Predicted)
• 密度：
  1.520±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2,2-三氯-1-氰基-1-苯基乙醇 在 吡啶 、 jones' reagent 、 草酰氯 、 二乙胺基三氟化硫 、 二异丁基氢化铝 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 、 苯 为溶剂， 反应 6.0h， 生成 1-phenylethyl α-fluoro-α-(trichloromethyl)phenylacetate
  参考文献：
  名称：

  Chemistry of novel compounds with multifunctional carbon structure. 9. Molecular design, synthetic studies, and NMR investigation of several efficient chiral derivatizing reagents which give very large 19F NMR .DELTA..delta. values in enantiomeric excess determination

  摘要：

  In order to develop efficient ee-determining reagents potentially superior to MTPA (1), some multifunctional compounds 2-5 were rationally designed. From NMR investigations of the analogous diastereomeric derivatives it was found that the chemical shift differences for each pair of diastereomers (DELTAdelta values) for CFPA derivatives 5d-f were approximately five times greater in F-19 NMR spectra and two times greater in H-1 NMR spectra than those of 1d-f. Synthesis of the optically pure CFPA, (-)-5a and (+)-5a, was achieved by nitrosation of each diastereomer of the optically active N-(1-phenylethyl)amides, 5f(M) and 5f(L), followed by thermal decomposition. Various derivatives were prepared by the condensation of 5b and lb with alcohol and amine nucleophiles, and both DELTAdelta(F) and DELTAdelta(H) Values were obtained for each compound. The CFPA derivatives 5d-m have proven to be significantly superior for ee determinations when compared to the corresponding MTPA derivatives 1d-m, particularly in compounds having remotely disposed chiral centers.

  DOI：

  10.1021/jo00059a036
• 作为产物：
  描述：

  三甲基氰硅烷 、 2,2,2-三氯苯乙酮 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 2,2,2-三氯-1-氰基-1-苯基乙醇
  参考文献：
  名称：

  Chemistry of novel compounds with multifunctional carbon structure. 9. Molecular design, synthetic studies, and NMR investigation of several efficient chiral derivatizing reagents which give very large 19F NMR .DELTA..delta. values in enantiomeric excess determination

  摘要：

  In order to develop efficient ee-determining reagents potentially superior to MTPA (1), some multifunctional compounds 2-5 were rationally designed. From NMR investigations of the analogous diastereomeric derivatives it was found that the chemical shift differences for each pair of diastereomers (DELTAdelta values) for CFPA derivatives 5d-f were approximately five times greater in F-19 NMR spectra and two times greater in H-1 NMR spectra than those of 1d-f. Synthesis of the optically pure CFPA, (-)-5a and (+)-5a, was achieved by nitrosation of each diastereomer of the optically active N-(1-phenylethyl)amides, 5f(M) and 5f(L), followed by thermal decomposition. Various derivatives were prepared by the condensation of 5b and lb with alcohol and amine nucleophiles, and both DELTAdelta(F) and DELTAdelta(H) Values were obtained for each compound. The CFPA derivatives 5d-m have proven to be significantly superior for ee determinations when compared to the corresponding MTPA derivatives 1d-m, particularly in compounds having remotely disposed chiral centers.

  DOI：

  10.1021/jo00059a036

文献信息

• A Novel Host Compound with High Inclusion Ability,<i>N</i>,<i>N</i>,<i>N</i>′,<i>N</i>′-Tetracyclohexyl-2,2′-biphenyldicarboxamide, and Crystal Structure of Its 1:1 Phenol Complex
  作者：Fumio Toda、Akihiro Kai、Yasunori Tagami、Thomas C. W. Mak

  DOI：10.1246/cl.1987.1393

  日期：1987.7.5

  The title host compound forms crystalline inclusion complexes with a wide variety of organic guest molecules. X-Ray analysis of its 1:1 complex with phenol shows that the two molecular components are held together by a O–H···O hydrogen bond of length 2.59(1) Å.

  标题宿主化合物与多种有机客体分子形成结晶包合物复合物。对其与苯酚的1:1复合物进行X射线分析显示，两个分子成分通过一个长度为2.59(1) Å 的O–H···O氢键相互结合。
• US7414078B2
  申请人：——

  公开号：US7414078B2

  公开（公告）日：2008-08-19