2-(3-bromophenyl)-2-chloropropane | 41937-72-8

• 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: 2-(3-bromophenyl)-2-chloropropane
• 英文别名: 1-bromo-3-(α-chloro-isopropyl)-benzene；1-Brom-3-(α-chlor-isopropyl)-benzol；1-Bromo-3-(2-chloropropan-2-yl)benzene；1-bromo-3-(2-chloropropan-2-yl)benzene
• CAS: 41937-72-8
• 化学式: C₉H₁₀BrCl
• 分子量: 233.535
• InChiKey: GHMZRRYDVJMAPK-UHFFFAOYSA-N

物化性质

• 沸点：
  244.0±15.0 °C(Predicted)
• 密度：
  1.396±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-(3-bromophenyl)-2-chloropropane 在 盐酸 、 正丁基锂 作用下， 以 二氯甲烷 为溶剂， 生成 2-<3-(N,N-dimethylcarbamoyl)-phenyl>-2-chloropropane
  参考文献：
  名称：

  Variable electronic properties of the CSNMe2 thioamide group

  摘要：

  The sigma-I value for the CSNMe2 group has been determined and the value of 0.23 indicates that this group is inductively electron withdrawing. The effect of the p-CSNMe2 group on the solvolysis rate of cumyl chloride has also been determined and, relative to the p-H analogue, this group has a negligible effect on rate. p-CSNMe2 substitution slows the hydrolysis rate of substituted benzaldehyde dimethyl acetals. p-CSNMe2 substitution enhances the solvolysis rate of ArCH(OMs)PO(OEt)2. These variable rate effects on reactions involving cationic intermediates have been interpreted in terms of variable electronic properties of the CSNMe2 group. This group can be cation stabilizing, electroneutral, or cation destabilizing, depending on the charge demands of specific cations. This is a result of a conjugative interaction of CSNMe2 with a cationic center and resultant delocalization of positive charge onto sulfur. The importance of such conjugation is a function of the amount of transition-state charge developed on the carbon bearing the CSNMe2 group. The electronic effects of the amphielectronic p-CSNMe2 group are compared to the more conventional effects of CONMe2 and the m-CSNMe2 analogues.

  DOI：

  10.1021/jo00013a038
• 作为产物：
  描述：

  2-羟基-2-(3-溴苯基)丙烷 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 生成 2-(3-bromophenyl)-2-chloropropane
  参考文献：
  名称：

  Variable electronic properties of the CSNMe2 thioamide group

  摘要：

  The sigma-I value for the CSNMe2 group has been determined and the value of 0.23 indicates that this group is inductively electron withdrawing. The effect of the p-CSNMe2 group on the solvolysis rate of cumyl chloride has also been determined and, relative to the p-H analogue, this group has a negligible effect on rate. p-CSNMe2 substitution slows the hydrolysis rate of substituted benzaldehyde dimethyl acetals. p-CSNMe2 substitution enhances the solvolysis rate of ArCH(OMs)PO(OEt)2. These variable rate effects on reactions involving cationic intermediates have been interpreted in terms of variable electronic properties of the CSNMe2 group. This group can be cation stabilizing, electroneutral, or cation destabilizing, depending on the charge demands of specific cations. This is a result of a conjugative interaction of CSNMe2 with a cationic center and resultant delocalization of positive charge onto sulfur. The importance of such conjugation is a function of the amount of transition-state charge developed on the carbon bearing the CSNMe2 group. The electronic effects of the amphielectronic p-CSNMe2 group are compared to the more conventional effects of CONMe2 and the m-CSNMe2 analogues.

  DOI：

  10.1021/jo00013a038

文献信息

• [EN] PROCESS FOR PREPARING N-(5-CHLORO-2-ISOPROPYLBENZYL)CYCLOPROPANAMINE<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION DE N-(5-CHLORO-2-ISOPROPYLBENZYL)CYCLOPROPANAMINE
  申请人：BAYER CROPSCIENCE AG

  公开号：WO2013160387A1

  公开（公告）日：2013-10-31

  The present invention relates to a process for preparing N-(5-chloro-2-isopropylbenzyl)cyclopropanamine by hydrogenation of N-[(5-chloro-2-isopropylphenyl)methylene]cyclopropanamine over specific platinum catalysts.

  本发明涉及一种通过在特定铂催化剂上对N-[(5-氯-2-异丙基苯基)亚甲基]环丙胺进行氢化制备N-(5-氯-2-异丙基苯基)环丙胺的方法。
• Rates of Solvolysis of the Halophenyldimethylcarbinyl Chlorides. The Effect of Halogen Substituents upon the Rates of Electrophilic Reactions^1-3
  作者：Herbert C. Brown、Y. Okamoto、George Ham

  DOI：10.1021/ja01565a037

  日期：1957.4
• PROCESS FOR PREPARING N-(5-CHLORO-2-ISOPROPYLBENZYL)CYCLOPROPANAMINE
  申请人：Bayer CropScience AG

  公开号：EP2841413A1

  公开（公告）日：2015-03-04
• Access to “Friedel–Crafts-Restricted” <i>tert</i>-Alkyl Aromatics by Activation/Methylation of Tertiary Benzylic Alcohols
  作者：Joshua A. Hartsel、Derek T. Craft、Qiao-Hong Chen、Ming Ma、Paul R. Carlier

  DOI：10.1021/jo202371c

  日期：2012.4.6

  Herein we describe a two-step protocol to prepare m-tert-alkylbenzenes. The appropriate tertiary benzylic alcohols are activated with SOCl2 or concentrated HCl and then treated with trimethylaluminum, affording the desired products in 68-97% yields (22 examples). This reaction sequence is successful in the presence of a variety of functional groups, including acid-sensitive and Lewis-basic groups. In addition to t-Bu groups, 1,1-dimethylpropyl and 1-ethyl-1-methylpropyl groups can also be installed using this method.
• Variable electronic properties of the CSNMe2 thioamide group
  作者：Xavier Creary、Timothy Aldridge

  DOI：10.1021/jo00013a038

  日期：1991.6

  The sigma-I value for the CSNMe2 group has been determined and the value of 0.23 indicates that this group is inductively electron withdrawing. The effect of the p-CSNMe2 group on the solvolysis rate of cumyl chloride has also been determined and, relative to the p-H analogue, this group has a negligible effect on rate. p-CSNMe2 substitution slows the hydrolysis rate of substituted benzaldehyde dimethyl acetals. p-CSNMe2 substitution enhances the solvolysis rate of ArCH(OMs)PO(OEt)2. These variable rate effects on reactions involving cationic intermediates have been interpreted in terms of variable electronic properties of the CSNMe2 group. This group can be cation stabilizing, electroneutral, or cation destabilizing, depending on the charge demands of specific cations. This is a result of a conjugative interaction of CSNMe2 with a cationic center and resultant delocalization of positive charge onto sulfur. The importance of such conjugation is a function of the amount of transition-state charge developed on the carbon bearing the CSNMe2 group. The electronic effects of the amphielectronic p-CSNMe2 group are compared to the more conventional effects of CONMe2 and the m-CSNMe2 analogues.