1-氯-1-甲基环己烷 | 931-78-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 中文名称: 1-氯-1-甲基环己烷
• 中文别名: 2-甲基吲哚嗪-6-碳酰氯
• 英文名称: 1-chloro-1-methylcyclohexane
• 英文别名: 1-Chlor-1-methylcyclohexan；1-Methylcyclohexylchlorid；1-methyl-1-chlorocyclohexane；1-Methyl-1-chlorcyclohexan；2-methyl-2-chlorocyclohexane
• CAS: 931-78-2
• 化学式: C₇H₁₃Cl
• mdl: MFCD00110789
• 分子量: 132.633
• InChiKey: OGYBTPYJHQSBBR-UHFFFAOYSA-N

物化性质

• 沸点：
  152 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  8
• 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

安全信息

• 海关编码：
  2903890090

反应信息

• 作为反应物：
  描述：

  1-氯-1-甲基环己烷 在 3,5-bis(4-methoxyphenyl)-1-phenylverdazyl 作用下， 以 环己烷 为溶剂， 生成 3-甲基-1-环己烯
  参考文献：
  名称：

  Kinetics and mechanism of unimolecular heterolysis of cage-like compounds: XIX. Effect of the nucleofuge nature on the activation parameters of heterolysis of 1-halo-1-methylcyclohexanes in cyclohexane. Heterolysis rate ratio in aprotic and protic solvents

  摘要：

  Heterolysis of 1-bromo-1-methylcyclohexane in cyclohexane (E1 reaction) involves solvation of the transition state (Delta S-not equal = -81 J mol(-1)K(-1)), while heterolysis of 1-chloro-1-methylcyclohexane is characterized by desolvation of the transition state (Delta S-not equal = 92 J mol(-1)K(-1)). The probability for the formation of transition state (interaction between cationoid intermediate and solvent cavity) increases in the first case due to enhanced stability of the solvated intermediate, and in the second, due to reduction in its size. The bromide/chloride heterolysis rate ratio decreases as the ionizing power of aprotic solvent decreases and that of protic solvent increases.

  DOI：

  10.1134/s1070428007010046
• 作为产物：
  描述：

  3-甲基-1-环己烯 在 盐酸 、 N,N-二甲基丙烯基脲 、 溶剂黄146 作用下， 以87%的产率得到1-氯-1-甲基环己烷
  参考文献：
  名称：

  Metal-free regioselective hydrochlorination of unactivated alkenesviaa combined acid catalytic system

  摘要：

  一个结合了盐酸/HCl、DMPU和乙酸的催化体系被用于对一系列未活化的烯烃进行氯化反应。

  DOI：

  10.1039/c7gc03665e
• 作为试剂：
  描述：

  3,4-二氢-2,4,6-三苯基-1,2,4,5-四嗪-1(2H)-基 在 1-氯-1-甲基环己烷 作用下， 以 正己烷 为溶剂， 生成 triphenylverdazylium chloride 、 2,4,6-三苯基-1,3-二氢-1,2,4,5-四嗪
  参考文献：
  名称：

  摘要：

  The kinetics of heterolysis of 1-chloro-1-methylcyclohexane in 9 protic and 25 aprotic solvents at 25degreesC were studied by the verdazyl method. The kinetic equation is nu = k[RCl] (El mechanism). The heterolysis rate of 1-chloro-1-methylcyclohexane in protic solvents is two orders of magnitude lower than that of 1-chloro-l-methylcyclopentane, whereas in low-polarity and nonpolar aprotic solvents the rates are close. A correlation analysis was made to reveal the solvation effects in heterolysis of both chlorides in a set of 9 protic and 25 aprotic solvents, and separately in protic and aprotic solvents.

  DOI：

  10.1023/a:1025112703599

文献信息

• [EN] ALANINE-BASED MODULATORS OF PROTEOLYSIS AND ASSOCIATED METHODS OF USE<br/>[FR] MODULATEURS DE PROTÉOLYSE À BASE D'ALANINE ET PROCÉDÉS D'UTILISATION ASSOCIÉS
  申请人：ARVINAS INC

  公开号：WO2017011590A1

  公开（公告）日：2017-01-19

  The description relates to inhibitors of Apoptosis Proteins (TAPs) binding compounds, including Afunctional compounds comprising the same, which find utility as modulators of targeted ubiquitination, especially inhibitors of a variety of polypeptides and other proteins which are degraded and/or otherwise inhibited by bifunctional compounds according to the present invention. In particular, the description provides compounds, which contain on one end a ligand which binds to the IAP E3 ubiquitin ligase and on the other end a moiety which binds a target protein such that the target protein is placed in proximity to the ubiquitin ligase to effect degradation (and inhibition) of that protein. Compounds can be synthesized that exhibit a broad range of pharmacological activities consistent with the degradation/inhibition of targeted polypeptides of nearly any type.

  描述涉及抑制凋亡蛋白（TAPs）结合化合物，包括包含相同的A功能化合物，这些化合物作为靶向泛素化的调节剂发挥作用，特别是根据本发明的双功能化合物抑制各种多肽和其他蛋白质的化合物。具体而言，描述提供了一端含有结合到IAP E3泛素连接酶的配体，另一端含有结合到靶蛋白的基团的化合物，使得靶蛋白靠近泛素连接酶以促使该蛋白的降解（和抑制）。可以合成化合物，表现出与几乎任何类型的靶向多肽的降解/抑制一致的广泛药理活性。
• The reaction between acyl halides and alcohols: Alkyl halide vs. Ester formation
  作者：Paolo Strazzolini、Angelo G. Giumanini、Giancarlo Verardo

  DOI：10.1016/s0040-4020(01)80747-x

  日期：1994.4

  therefore, ester formation practically confined to a triggering role. But, in those cases where the cation is less easily formed, ester formation was favoured and, consequently, became the necessary elementary step towards alkyl halide formation. This final product, on the other hand, might be extremely slow to form in an SN2 reaction between the protonated ester function and the halide ion. In these hnstances

  在酰基卤和醇之间的反应中，热力学上有利的产物是游离羧酸和烷基卤。最初的反应通常是形成酯和HHal。当该醇非常容易被HHal质子化时产生烷基阳离子时，形成的H 2 O表现出超活性，并且与该醇成功竞争了酰基卤的制备，因此，酯的形成实际上局限于触发作用。但是，在那些阳离子不易形成的情况下，有利于酯的形成，因此成为形成卤代烷的必要的基本步骤。另一方面，最终产品在S N中的形成速度可能非常慢2质子化的酯官能团与卤离子之间的反应。因此，在这些情况下，以及在碱性溶剂竞争HHal质子的情况下，酯都是最终产物。α-羟基，α-苯基苯乙酸（2y）给出了上述虚线所示的一个显着例外，它似乎通过季中间体（E）进行了直接的氯-羟基交换，最后塌陷为α-氯- α-苯基苯乙酸（4y）。在严格相似的条件下，使用CH 2 Cl 2作为溶剂比较了不同的系统。测试了约28种不同的底物与AcCl（1a）的反应，而八种酰基卤（1）对（R
• Reactivity of bismuth(III) halides towards alcohols. A tentative to mechanistic investigation
  作者：El Mehdi Keramane、Bernard Boyer、Jean-Pierre Roque

  DOI：10.1016/s0040-4020(01)00013-8

  日期：2001.3

  bismuth(III) halides (BiX3; X=Cl, Br and I) towards a series of alcohols has been investigated. Three different reactions have been studied, namely: halogenation, dehydration and etherification. The behaviour of these bismuth derivatives was found to depend on the nature of the halide bonded to the bismuth atom. Their reactivities can be interpreted on the basis of the Hard and Soft Acids and Bases

  研究了卤化铋（III）（BiX 3； X = Cl，Br和I）对一系列醇的反应性。已经研究了三种不同的反应，即：卤化，脱水和醚化。发现这些铋衍生物的行为取决于结合到铋原子上的卤化物的性质。它们的反应性可以根据硬酸和软酸和碱（HSAB）原理进行解释。提出了一种机制，该机制涉及形成醇与Bi（III）的复合物。
• Silica gel-mediated hydrohalogenation of unactivated alkenes using hydrohalogenic acids under organic solvent-free conditions
  作者：Kiyoshi Tanemura

  DOI：10.1016/j.tetlet.2018.10.043

  日期：2018.12

  Silica gel-mediated hydrochlorination of unactivated alkenes using 35% hydrochloric acid under organic solvent-free conditions proceeded to give the corresponding chlorides in good yields. Hydrobromination or hydriodination using 47% hydrobromic acid or 55% hydriodic acid afforded the corresponding halides, respectively. Silica gel could be recycled five times without any significant loss of activities

  在无有机溶剂的条件下，使用35％盐酸进行硅胶介导的未活化烯烃的氢氯化反应，得到了相应的氯化物，收率很高。使用47％氢溴酸或55％氢碘酸进行氢溴化或氢碘化分别得到相应的卤化物。硅胶可以循环使用五次，而不会造成任何明显的活性损失。
• Efficient coupling of tertiary alkyl halides with dialkylzinc and titanium compounds
  作者：Manfred T. Reetz、Bernd Wenderoth、Roland Peter、Rainer Steinbach、J�rgen Westermann

  DOI：10.1039/c39800001202

  日期：——

  Dialkylzinc compounds react with tertiary alkyl halides to afford the corresponding coupling products containing a quaternary carbon atom, thereby making geminal dialkylation of ketones or hydroalkylation of olefins possible.

  二烷基锌化合物与叔烷基卤化物反应，得到相应的含有季碳原子的偶联产物，从而使酮的双二烷基化或烯烃的加氢烷基化成为可能。