2,3-二氯-2,3-二甲基丁烷 | 594-85-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氯化物
• 中文名称: 2,3-二氯-2,3-二甲基丁烷
• 英文名称: 2,3-dichloro-2,3-dimethylbutane
• 英文别名: 2,3-Dichlor-2,3-dimethyl-butan
• CAS: 594-85-4
• 化学式: C₆H₁₂Cl₂
• 分子量: 155.067
• InChiKey: SJBPUCQFQDUICP-UHFFFAOYSA-N

物化性质

• 熔点：
  159-160 °C
• 沸点：
  142.4±8.0 °C(Predicted)
• 密度：
  1.030±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  2,3-二氯-2,3-二甲基丁烷 在 溴 、 potassium carbonate 、 Petroleum ether 作用下， 生成 3,4-二溴-2,3-二甲基-丁-1-烯
  参考文献：
  名称：

  Kondakow, Journal fur praktische Chemie (Leipzig 1954), 1900, vol. <2>62, p. 171

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯-2,3-二甲基-3-亚硝基丁烷 在 苯 作用下， 生成 2,3-二氯-2,3-二甲基丁烷
  参考文献：
  名称：

  Hammick; Lister, Journal of the Chemical Society, 1937, p. 490

  摘要：

  DOI：

文献信息

• Flash vacuum pyrolysis over magnesium. Part 1. Pyrolysis of benzylic, other aryl/alkyl and aliphatic halides
  作者：R. Alan Aitken、Philip K. G. Hodgson、John J. Morrison、Adebayo O. Oyewale

  DOI：10.1039/b108663d

  日期：2002.1.23

  Flash vacuum pyrolysis over a bed of freshly sublimed magnesium on glass wool results in efficient coupling of benzyl halides to give the corresponding bibenzyls. Where an ortho halogen substituent is present further dehalogenation gives some dihydroanthracene and anthracene. Efficient coupling is also observed for halomethylnaphthalenes and halodiphenylmethanes while chlorotriphenylmethane gives 4,4′-bis(diphenylmethyl)biphenyl. By using α,α′-dihalo-o-xylenes, benzocyclobutenes are obtained in good yield, while the isomeric α,α′-dihalo-p-xylenes give a range of high thermal stability polymers by polymerisation of the initially formed p-xylylenes. Other haloalkylbenzenes undergo largely dehydrohalogenation where this is possible, in some cases resulting in cyclisation. Deoxygenation is also observed with haloalkyl phenyl ketones to give phenylalkynes as well as other products. With simple alkyl halides there is efficient elimination of HCl or HBr to give alkenes. For aliphatic dihalides this also occurs to give dienes but there is also cyclisation to give cycloalkanes and dehalogenation with hydrogen atom transfer to give alkenes in some cases. For 5-bromopent-1-ene the products are those expected from a radical pathway but for 6-bromohex-1-ene they are clearly not. For 2,2-dichloropropane and 1,1-dichloropropane elimination of HCl occurs but for 1,1-dichlorobutane, -pentane and -hexane partial hydrolysis followed by elimination of HCl gives E,E-, E,Z- and Z,Z- isomers of the dialk-1-enyl ethers and fully assigned 13C NMR data are presented for these. With 6-chlorohex-1-yne and 7-chlorohept-1-yne there is cyclisation to give methylenecycloalkanes and -cycloalkynes. The behaviour of 1,2-dibromocyclohexane and 1,2-dichlorocyclooctane under these conditions is also examined. Various pieces of evidence are presented that suggest that these processes do not involve generation of free gas-phase radicals but rather surface-adsorbed organometallic species.

  在玻璃棉上覆盖一层新升华的镁,进行闪式真空热解,能有效促使苄基卤化物耦合生成相应的联苄。当有邻位卤素取代基存在时,进一步脱卤生成部分二氢蒽和蒽。卤甲基萘和二苯基甲烷也能高效耦合,而三苯基氯甲烷则生成4,4′-双(二苯甲基)联苯。用α,α′-二卤代邻二甲苯可以获得较高产率的苯并环丁烯,而异构的α,α′-二卤代对二甲苯,通过形成的对二甲苯的聚合,可以得到一系列高热稳定性的聚合物。其他卤代烃苯大体上会脱卤化氢,某些情况下能产生环化反应。同样可以观察到,苯基卤代烷烃脱去羰基生成苯乙炔以及其他产物。简单的烷基卤化物则高效地脱去HCl或HBr生成烯烃。脂肪族二卤化物也会发生这一反应生成二烯,但不发生环化反应生成环烷烃,或在某些情况下发生氢原子转移的脱卤反应生成烯烃。5-溴戊-1-烯的产物符合自由基途径的预期,但6-溴己-1-烯并不符合。2,2-二氯丙烷和1,1-二氯丙烷能脱去HCl,但1,1-二氯丁烷、戊烷和己烷则能部分水解,随后脱去HCl,生成E,E-, E,Z-和Z,Z-异构体二烷-1-烯基醚,并且得到了这些物质的13C NMR全归属数据。6-氯己-1-炔和7-氯庚-1-炔能发生环化反应生成亚甲基环烷烃和环炔烃。本文还考察了1,2-二溴环己烷和1,2-二氯环辛烷在上述条件下的行为。本文给出了众多种证据,表明这些反应过程不涉及气相自由基的形成,而是表面吸附的金属有机物种。
• The cis chlorination of alkenes using selenium reagents
  作者：Angelo M. Morella、A.David Ward

  DOI：10.1016/s0040-4039(01)91559-x

  日期：——

  The phenylselenenyl chloride adduct from alkenes can be oxidised and the selenomoiety can be displaced by chloride to give high yields of dichlorides with cis geometry.

  来自烯烃的苯基硒烯基氯加合物可以被氧化，并且硒基可以被氯取代，从而得到高产率的具有顺式几何形状的二氯化物。
• Restricted 9-cis-retinoids
  申请人：American Cyanamid Company

  公开号：EP0718285A2

  公开（公告）日：1996-06-26

  The invention is novel analogs of 9-cis-retinoic acid which are useful for the treatment and prevention of coronary artery disease and to protect against premature atherosclerosis by increasing HDL levels. The invention includes processes for preparing the novel 9-cis-retinoic acid analogs.

  本发明是新型 9-顺式维甲酸类似物，可用于治疗和预防冠状动脉疾病，并通过提高高密度脂蛋白水平防止动脉粥样硬化过早发生。本发明包括制备新型 9-顺式维甲酸类似物的工艺。
• Restricted 9-cis retenoids
  申请人：American Cyanamid Company

  公开号：EP0997455A1

  公开（公告）日：2000-05-03

  The invention is novel analogs of 9-cis-retinoic acid which are useful for the treatment and prevention of coronary artery disease and to protect against premature atherosclerosis by increasing HDL levels. The invention includes processes for preparing the novel 9-cis-retinoic acid analogs.

  本发明是新型 9-顺式维甲酸类似物，可用于治疗和预防冠状动脉疾病，并通过提高高密度脂蛋白水平防止动脉粥样硬化过早发生。本发明包括制备新型 9-顺式维甲酸类似物的工艺。
• Reaction of Aromatic and Unsaturated Compounds with the Potassium Permanganate/HCl (HBr) Acetonitrile Reagent
  作者：Lilian Kao Liu、Ching-Shan Lin

  DOI：10.1002/jccs.199600010

  日期：1996.2

  AbstractAddition of hydrochloric or hydrobromic acid to a solution of potassium permanganate in acetonitrile produced a homogeneous mixture, which is suitable for laboratory chlorination or bromination, respectively. Aromatic compounds more reactive than alkylbenzenes can be chlorinated or brominated without additional catalyst. Alkenes and alkynes give the corresponding vicinal dihaloalkanes and vinyl halides. All reactions complete within two hours under mild condition (25‐60 °C) with excellent to moderate yields.