1,3-二氯-1,3-二苯基丙烷 | 180847-73-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 中文名称: 1,3-二氯-1,3-二苯基丙烷
• 英文名称: 1,3-Dichloro-1,3-diphenylpropane
• 英文别名: Benzene, 1,1'-(1,3-dichloro-1,3-propanediyl)bis-；(1,3-dichloro-3-phenylpropyl)benzene
• CAS: 180847-73-8
• 化学式: C₁₅H₁₄Cl₂
• 分子量: 265.182
• InChiKey: MWJZAXFDXAXVBL-UHFFFAOYSA-N

物化性质

• 沸点：
  359.2±37.0 °C(Predicted)
• 密度：
  1.185±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  1,3-二氯-1,3-二苯基丙烷 以 various solvent(s) 为溶剂， 生成
  参考文献：
  名称：

  Flash Photolysis of 1,3-Dichloro-1,3-diphenylpropane in Polar Solvents:  Generation of a Stabilized γ-Chloropropyl Cation, Subsequent Formation of a Propenyl Cation, and Nucleophilic Trapping of Both Cations

  摘要：

  Photolysis of 1,3-dichloro-1,3-diphenylpropane (1) in 2,2,2-trifluoroethanol at 266 nm leads to a gamma-chloropropyl cation (2a) following loss of chloride ion. Kinetic evidence has been obtained for the interconversion between the open chain cation and the corresponding cyclic chloronium ion (2b); thermal loss of hydrogen chloride gives the 1,3-diphenyl-2-propenyl cation (3). The formation of this species occurs through a monophotonic process; the involvement of a two-photon process in the photoheterolysis of dihalide 1 has been ruled ou-e by studying the formation of cation 3 from 1 at different laser intensities. The lack of power dependence implies that 3-chloro-1,3-diphenylpropene (4) is not an intermediate in the photoheterolysis of dihalide 1. The reaction of both cationic intermediates (2 and 3) with different nucleophiles has also been examined. Finally, two-laser two-photon experiments have allowed the study of the photoisomerization of E,E-3 into Z,E-3.

  DOI：

  10.1021/jp9814449
• 作为产物：
  描述：

  (反式)-1,1'-(1,2-环丙烷二基)二苯 在 亚硝酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以82%的产率得到3,5-二苯基-2-异恶唑啉
  参考文献：
  名称：

  由芳基环丙烷和亚硝基氯合成4,5-二氢异恶唑

  摘要：

  Arylcyclopropanes readily react with nitrosyl chloride in liquid sulfur dioxide to give the corresponding 5-aryl-4,5-dihydroisoxazoles in good yield. The reaction is most selective at -40 to -50degreesC; at higher temperature, the contribution of side processes becomes appreciable. The complete conversion of arylcyclopropanes containing donor substituents is attained with the use of 1.5 equiv of nitrosyl chloride, while the rate of the transformation of compounds with nonactivated aromatic rings considerably increases on raising the molar ratio NOCl-arylcyclopropane.

  DOI：

  10.1023/b:rujo.0000003196.89457.a4

文献信息

• Lamp versus laser photolysis of 1,3-dichloro-1,3-diphenylpropane in cyclohexane. Direct observation of 1,3-diphenylpropenyl radical
  作者：Julia Pérez-Prieto、Miguel Angel Miranda、Enrique Font-Sanchis、Klára Kónya、J.C. Scaiano

  DOI：10.1016/0040-4039(96)00987-2

  日期：1996.7

  Laser photolysis of the title compound leads to two-photon processes indicating the involvement of the 1,3-diphenylpropanediyl biradical (12) and the 1,3-diphenylallyl radical (10).

  标题化合物的激光光解导致出现两个光子过程，表明存在1,3-二苯基丙烷二基双自由基（12）和1,3-二苯基烯丙基（10）。
• Lewis Acid Mediated Reactions of Aldehydes with Styrene Derivatives:  Synthesis of 1,3-Dihalo-1,3-diarylpropanes and 3-Chloro-1,3-diarylpropanols
  作者：George W. Kabalka、Zhongzhi Wu、Yuhong Ju、Min-Liang Yao

  DOI：10.1021/jo051298k

  日期：2005.12.1

  The reactions of aryl aldehydes with styrene derivatives, mediated by various boron Lewis acids, were investigated. 1,3-Dihalo-1,3-diarylpropanes were obtained in high yields with boron trihalides, while 3-chloro-1,3-diarylpropanols were obtained in good to excellent yields with phenylboron dichloride. Reactions involving nonenolizable aliphatic aldehydes, trans-cinnamaldehyde, and β-substituted styrenes

  研究了各种硼路易斯酸介导的芳基醛与苯乙烯衍生物的反应。用三卤化硼以高收率得到1,3-二卤代-1,3-二芳基丙烷，而用二氯化苯硼以高收率得到3-氯-1,3-二芳基丙醇。还首次研究了涉及不可烯化的脂族醛，反式肉桂醛和β-取代的苯乙烯的反应。
• A New Convenient, Efficient, and Regioselective Synthesis of 1,3-Diaryl- 1,3-dihalopropanes
  作者：George Kabalka、Zhongzhi Wu、Yuhong Ju

  DOI：10.1055/s-2004-829191

  日期：——

  Reactions of aryl aldehydes with styrenes in the presence of boron trihalides produce 1,3-diaryl-1,3-dihalopropanes in excellent yields.

  芳基醛与苯乙烯在三卤化硼存在下反应，生成1,3-二芳基-1,3-二卤丙烷，产率极高。
• Microwave-assisted cyclocondensation of hydrazine derivatives with alkyl dihalides or ditosylates in aqueous media: syntheses of pyrazole, pyrazolidine and phthalazine derivatives
  作者：Yuhong Ju、Rajender S. Varma

  DOI：10.1016/j.tetlet.2005.07.018

  日期：2005.9

  Direct syntheses of 4,5-dihydro-pyrazole, pyrazolidine, and 1,2-dihydro-phthalazine derivatives via double-alkylation of hydrazines by alkyl dihalides or ditosylates were accomplished in aqueous media under microwave irradiation conditions; the environmentally friendlier chemical transformation occurred in a single step and eliminated the use of expensive metal catalysts in building two C–N bonds.

  在微波辐射条件下，在含水介质中，通过烷基二卤化物或二甲苯磺酸盐对肼的双烷基化反应，直接合成4，5-二氢吡唑，吡唑烷和1，2-二氢邻苯二甲酰肼衍生物。有利于环境的化学转化过程一步完成，消除了使用昂贵的金属催化剂来构建两个C–N键的过程。
• Boron trihalide-promoted addition of aryl aldehydes to styrenes. A new convenient and highly efficient synthesis of 1,3-dihalo-1,3-diarylpropanes
  作者：George W Kabalka、Zhongzhi Wu、Yuhong Ju

  DOI：10.1016/s0040-4039(01)01125-x

  日期：2001.8

  Reactions of aryl aldehydes with styrenes in the presence of boron trichloride in CH2Cl2 at 0°C produce 1,3-dichloro-1,3-diarylpropanes in excellent yields. Reactions carried out using boron tribromide generate the corresponding 1,3-dibromo-1,3-diarylpropane in good yields.

  芳基醛与苯乙烯在三氯化硼的存在下于0°C于CH 2 Cl 2中反应可生成1,3-二氯-1,3-二芳基丙烷，产率极高。使用三溴化硼进行的反应以良好的产率产生相应的1，3-二溴-1，3-二芳基丙烷。