1,2-二氯环辛烷 | 26601-20-7

• 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: 1,2-二氯环辛烷
• 英文名称: 1,2-dichlorocyclooctane
• 英文别名: 1,2-dichloro-cyclooctane；1,2-Dichlor-cyclooctan
• CAS: 26601-20-7
• 化学式: C₈H₁₄Cl₂
• 分子量: 181.105
• InChiKey: KHSNPEAMNSUMAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• 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：

  1,2-二氯环辛烷 在 lithium amalgam 、 potassium tert-butylate 作用下， 以 乙醚 为溶剂， 生成 环辛炔
  参考文献：
  名称：

  Wittig,G.; Pohlke,R., Chemische Berichte, 1961, vol. 94, p. 3276 - 3286

  摘要：

  DOI：
• 作为产物：
  描述：

  氧化环辛烯 在 COCl₂ 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1,2-二氯环辛烷
  参考文献：
  名称：

  Ziegenbein,W.; Hornung,K.H., Chemische Berichte, 1962, vol. 95, p. 2976 - 2983

  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。
• <i>vic</i>-Dichlorination of Olefins with Sodium Chlorite, Mn(acac)₃, and Moist Alumina in Dichloromethane
  作者：Shigetaka Yakabe、Masao Hirano、Takashi Morimoto

  DOI：10.1080/00397919808007018

  日期：1998.5

  Abstract Aliphatic, alicyclic, and aromatic alkenes underwent smooth vic-dichlorination upon treatment with a reagent combination of NaClO2, Mn(acac)3 catalyst, and chromatographic neutral alumina preloaded with a small amount of water in dichloromethane under mild conditions.

  摘要 脂肪族、脂环族和芳香族烯烃在温和的条件下，在氯化钠溶液、Mn(acac)3 催化剂和预载少量水的二氯甲烷中的色谱中性氧化铝的试剂组合处理后，经历了平滑的二氯化反应。
• Simple and practical halogenation of arenes, alkenes and alkynes with hydrohalic acid/H2O2 (or TBHP)
  作者：Nivrutti B. Barhate、Anil S. Gajare、Radhika D. Wakharkar、Ashutosh V. Bedekar

  DOI：10.1016/s0040-4020(99)00628-6

  日期：1999.9

  hydrogen peroxide (34 %) or tert-butylhydroperoxide (70 %) and hydrohalic acid is presented. A similar procedure of oxyhalogenation involving the in situ generation of positive halogen reagents is applied for the preparation of vicinal trans-dibromoalkanes and dichloroalkanes from alkenes. The reaction of alkenes with a combination of hydrochloric acid and hydrobromic acid with hydrogen peroxide gave a

  提出了使用过氧化氢水溶液（34％）或叔丁基氢过氧化物（70％）和氢卤酸的组合物来卤代芳烃的简单方案。涉及原位产生正卤素试剂的类似的氧卤化方法可用于由烯烃制备邻位的反式-二溴代烷烃和二氯烷烃。烯烃与盐酸和氢溴酸的组合与过氧化氢的反应得到了1-溴2-氯烷烃和1,2-二溴烷烃的混合物。也有类似条件下炔烃的氧化溴化。
• Chlorination of alkenes by manganese(III) chloride species
  作者：K.D. Donnelly、W.E. Fristad、B.J. Gellerman、J.R. Peterson、B.J. Selle

  DOI：10.1016/s0040-4039(00)99950-7

  日期：1984.1

  Several manganese(III) chloride species have been prepared in situ and used as effective chlorinating agents of alkenes.

  已经就地制备了几种氯化锰（III），并用作烯烃的有效氯化剂。
• Chlorination of Alkenes with MnO₂-MnCl₂-Acetyl Chloride in Dimethyl Formamide
  作者：Franco Bellesia、Franco Ghelfi、Ugo M. Pagnoni、Adriano Pinetti

  DOI：10.1080/00397919108016774

  日期：1991.2

  Abstract Chlorination of alkenes was achieved in high yields by MnO2-MnCl2-Acetyl Chloride in dimethylformamide. A Mn(III) intermediate and a ligand-transfer process are suggested.

  摘要 MnO2-MnCl2-乙酰氯在二甲基甲酰胺中以高收率实现了烯烃的氯化。建议使用 Mn(III) 中间体和配体转移过程。