(R)-(+)-1,1-dichloro-2-(2-chlorophenyl)-2-(4-chlorophenyl)ethane | 164203-73-0

• 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: (R)-(+)-1,1-dichloro-2-(2-chlorophenyl)-2-(4-chlorophenyl)ethane
• 英文别名: Mitotane, (R)-；1-chloro-2-[(1R)-2,2-dichloro-1-(4-chlorophenyl)ethyl]benzene
• CAS: 164203-73-0
• 化学式: C₁₄H₁₀Cl₄
• 分子量: 320.045
• InChiKey: JWBOIMRXGHLCPP-CYBMUJFWSA-N

物化性质

• 沸点：
  398.9±37.0 °C(Predicted)
• 密度：
  1.372±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  米托坦 在 Daicel Chiralcel OJ-H column 作用下， 生成 (R)-(+)-1,1-dichloro-2-(2-chlorophenyl)-2-(4-chlorophenyl)ethane 、 (S)-(-)-1,1-dichloro-2-(2-chlorophenyl)-2-(4-chlorophenyl)ethane
  参考文献：
  名称：

  通过o，p' - DDT和o，p' - DDD的圆二色性中独特的分子内激子偶联确定绝对构型。实验与理论研究相结合†

  摘要：

  所述的圆形dichroisms（CDS）ø，p '的1,1,1-三氯和1,1-二氯-2,2-双（氯苯基） -异构体乙烷（DDT和DDD）进行了实验和理论研究。在这些持久性有机污染物的CD光谱中，观察到了一系列强烈的棉花效应峰，这些峰以特征性的负-负-正-负模式或镜像模式出现。SAC-CI / B95（d）和RI-CC2 / def2-TZVPP水平的理论CD光谱很好地再现了实验光谱，使我们能够明确地将（+）- DDT和（-）- DDD的绝对构型指定为小号。

  DOI：

  10.1039/c6pp00438e

文献信息

• Isomer-selective and enantiomer-selective determination of DDT and related compounds using chiral high-resolution gas chromatography/mass spectrometry and chiral HPLC.
  作者：Hans-Rudolf. Buser、Markus D. Mueller

  DOI：10.1021/ac00111a030

  日期：1995.8.1

  The composition of technical DDT was investigated using achiral and chiral high-resolution gas chromatography (HRGC) and electron-ionization mass spectrometry (EI-MS), 2,4'-DDT and 2,4'-DDD, two important components of technical DDT, were enantiomerically resolved by chiral HRGC with silylated beta-cyclodextrin and by chiral highperformance chromatography (HPLC) with permethylated gamma-cyclodextrin as chiral selectors, The (+)- and (-)-enantiomers were assigned by chiral HPLC using chiroptical measurements, Enantiopure isolates were then used to identify these enantiomers in chiral HRGC analyses, Previous data indicated (+)- and (-)-2,4'-DDT to have S- and R-configuration, respectively, brat the absolute configurations for (+)- and (-)-2,4'-DDD were hitherto unknown, They were now assigned via the reductive dechlorination of the individual 2,4'-DDT enantiomers which proceeded stereoselectively to the corresponding 2,4'-DDD enantiomers, The results showed (+)- and (-)-2,4'-DDD to have R- and S-configuration, respectively, The enantiomers of 2,4'-DDD thus have reversed signs of rotation for polarized light compared to the enantiomers of 2,4'-DDT with the same configuration, The enantiomer resolution of several additional chiral compounds in technical DDT is reported; enantiomeric ratios of approximate to 1.0 indicated all chiral compounds to be present as racemates in the technical and in the synthetic reference materials, We report the first enantioselective determinations of technical DDT; the methods presented should also be applicable to the analysis of environmental and biological samples.
• Absolute configuration determination through the unique intramolecular excitonic coupling in the circular dichroisms of o,p′-DDT and o,p′-DDD. A combined experimental and theoretical study
  作者：Hiroki Tanaka、Yoshihisa Inoue、Takeshi Nakano、Tadashi Mori

  DOI：10.1039/c6pp00438e

  日期：2017.4

  Circular dichroisms (CDs) of the o,p′-isomers of 1,1,1-trichloro- and 1,1-dichloro-2,2-bis(chlorophenyl)ethanes (DDT and DDD) were investigated experimentally and theoretically. A series of strong Cotton effect peaks in a characteristic negative–negative–positive–negative, or its mirror-imaged, pattern were observed in the CD spectra of these persistent organic pollutants. The theoretical CD spectra

  所述的圆形dichroisms（CDS）ø，p '的1,1,1-三氯和1,1-二氯-2,2-双（氯苯基） -异构体乙烷（DDT和DDD）进行了实验和理论研究。在这些持久性有机污染物的CD光谱中，观察到了一系列强烈的棉花效应峰，这些峰以特征性的负-负-正-负模式或镜像模式出现。SAC-CI / B95（d）和RI-CC2 / def2-TZVPP水平的理论CD光谱很好地再现了实验光谱，使我们能够明确地将（+）- DDT和（-）- DDD的绝对构型指定为小号。