4-氯苯甲酸环己酯 | 58435-20-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-氯苯甲酸环己酯
• 英文名称: cyclohexyl 4-chlorobenzoate
• CAS: 58435-20-4
• 化学式: C₁₃H₁₅ClO₂
• 分子量: 238.714
• InChiKey: XYZQVOFIZXZLFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-氯苯甲酸环己酯 在 甲基(三氟甲基)-1,3-二环氧丙烷 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以40%的产率得到4-Chloro-benzoic acid 3-oxo-cyclohexyl ester
  参考文献：
  名称：

  Oxyfunctionalization of Aliphatic Esters by Methyl(trifluoromethyl)dioxirane

  摘要：

  The oxidation of lineal, cyclic, and bicyclic aliphatic p-chlorobenzoic and p-chorobenzenesulfonic acid esters 2 with methyl(trifluoromethyl)dioxirane (TFDO) (1) occurs at positions in the hydrocarbon chain distant from the directing group with a significant degree of selectivity to give the corresponding keto or hydroxy esters. Compounds 2 are relatively deactivated with respect to this oxidation due to the electron-withdrawing nature of the ester moiety. Methylene C-alpha-H and C-beta-H bonds remain unchanged in all cases, but tertiary C-beta-H bonds undergo oxidation with TFDO (1). Stereoelectronic factors are used to explain the faster reaction rate in competition experiments for the oxidation of endo-norbornyl ester 2h than for its exo-isomer 2g.

  DOI：

  10.1021/jo9604189
• 作为产物：
  描述：

  4-氯苯甲酸酐 以18%的产率得到
  参考文献：
  名称：

  KUDO TADAHIRO; NOSE ATSUKO, YAKUGAKU DZASSI, YAKUGAKU ZASSNI, J. PHARM. SOS. JAR. , 1975, 95+

  摘要：

  DOI：

文献信息

• Generally applicable and efficient esterification of aldehydes with alcohols catalyzed by cyclopalladated ferrocenylimine
  作者：Gaizhi Ma、Yuting Leng、Huijie Qiao、Fan Yang、Shiwei Wang、Yangjie Wu

  DOI：10.1002/aoc.3069

  日期：2014.1

  The palladacycle‐catalyzed esterification of a variety of aldehydes with alcohols was developed. This reaction allows formation of esters in moderate to excellent yields not only for various aldehydes but also alcohols. In addition, the esterification could proceed well under mild conditions with a low catalyst loading of 0.0625 mol%. Copyright © 2013 John Wiley & Sons, Ltd.

  开发了由palladacycle催化的各种醛与醇的酯化反应。该反应使得不仅对于各种醛而且对于醇，都以中等至优异的产率形成酯。另外，在0.0625mol％的低催化剂负载下，酯化可以在温和的条件下很好地进行。版权所有©2013 John Wiley＆Sons，Ltd.
• Aerobic oxidative esterification and thioesterification of aldehydes using dibromoisocyanuric acid under mild conditions: no metal catalysts required
  作者：Young-Do Kwon、Minh Thanh La、Hee-Kwon Kim

  DOI：10.1039/c8nj01085d

  日期：——

  thioesters were synthesized by oxidative esterification and thioesterification via in situ generated acyl bromide intermediates, which were used to react with various alcohols and thiols. The esterification and thioesterification were readily performed in the presence of dibromoisocyanuric acid in dichloromethane, without any metal catalysts and under mild conditions. By using this reaction protocol

  描述了一种从醛直接制备酯和硫代酯的实用直接方法。通过原位产生的酰基溴中间体通过氧化酯化和硫酯化反应合成酯和硫代酯，这些中间体可与各种醇和硫醇反应。酯化和硫代酯化反应很容易在二氯甲烷中存在二溴异氰尿酸的情况下进行，无需任何金属催化剂，并且在温和的条件下进行。通过使用该反应方案，可以高收率制备各种酯和硫代酯。这种有效的方法为醛的简便酯化和硫酯化提供了一种有希望的方法。
• Studies of the Electronic Effects of Zinc Cluster Catalysts and Their Application to the Transesterification of β‐Keto Esters
  作者：Kazushi Agura、Yukiko Hayashi、Mari Wada、Daiki Nakatake、Kazushi Mashima、Takashi Ohshima

  DOI：10.1002/asia.201600062

  日期：2016.5.20

  The electronic effects of tetranuclear zinc cluster catalysts on transesterification were investigated by changing the carboxylate ligands in the clusters. High catalyst activity crucially depended on the balance between Lewis acidity and Brønsted basicity of the catalyst; this was consistent with the dual activation of both the electrophile and nucleophile by the cooperative zinc centers. In addition

  通过改变簇中的羧酸根配体，研究了四核锌簇催化剂对酯交换反应的电子效应。催化剂的高活性关键取决于路易斯酸度和布朗斯台德碱度之间的平衡。这与锌配合中心对亲电试剂和亲核试剂的双重激活是一致的。此外，四核锌簇催化剂实现了β-酮酯的酯交换，具有前所未有的广泛的底物通用性，其中新开发的五氟丙酸酯桥连的锌簇和4-二甲基氨基吡啶添加剂极大地提高了空间拥挤的α-和α的反应性， α-二取代的β-酮酸酯。
• Synthesis and NMR spectroscopic conformational analysis of benzoic acid esters of mono- and 1,4-dihydroxycyclohexane, 4-hydroxycyclohexanone and the -ene analogue – The more polar the molecule the more stable the axial conformer
  作者：Erich Kleinpeter、Peter Werner、Torsten Linker

  DOI：10.1016/j.tet.2017.04.029

  日期：2017.7

  para-Substituted benzoic acid esters of cyclohexanol, 1,4-dihydroxycyclohexane, 4-hydroxy-cyclohexanone and of the corresponding exo-methylene derivative were synthesized and the conformational equilibria of the cyclohexane skeleton studied by low temperature 1H and 13C NMR spectroscopy. The geometry optimized structures of the axial/equatorial chair conformers were computed at the DFT level of theory

  合成了环己醇，1，4-二羟基环己烷，4-羟基-环己酮和相应的外亚甲基衍生物的对位取代的苯甲酸酯，并通过低温1 H和13 C NMR光谱研究了环己烷骨架的构象平衡。在理论的DFT级别上计算了轴向/赤道座椅贴合器的几何优化结构。分别对于轴向和赤道构象异构体仅获得酯基的一种优选构象。轴向含量构象子随6-元环部分极性的增加而增加；因此，此外，严格评估了sp 2杂交/ C（4）= O / C（4）= CH 2的极性对当前构象平衡的影响。可以首次研究这种化合物的另一种动态过程。
• On the understanding of BF₃·Et₂O-promoted intra- and intermolecular amination and oxygenation of unfunctionalized olefins
  作者：Chun-Hua Yang、Wen-Wen Fan、Gong-Qing Liu、Lili Duan、Lin Li、Yue-Ming Li

  DOI：10.1039/c5ra10513g

  日期：——

  for both intra- and intermolecular amination and oxygenation of unfunctionalized olefins. In the presence of 3 equiv. of BF3·Et2O, intramolecular hydroamination of N-(pent-4-enyl)-p-toluenesulfonamides, N-(hex-5-enyl)-p-toluenesulfonamides, intermolecular hydroamination between sulfonamides and cyclohexene, norbornene or styrene, lactonization of pent-4-enoic acid or hex-5-enoic acid compounds and esterification

  发现BF 3 ·Et 2 O对于未官能化的烯烃的分子内和分子间胺化和氧合都是有效的。在3当量的存在下。BF 3 ·Et 2 O的合成，N-（戊-4-烯基）-对甲苯磺酰胺，N-（六-5-烯基）-p的分子内加氢胺化-甲苯磺酰胺，磺酰胺与环己烯，降冰片烯或苯乙烯之间的分子间加氢胺化，戊-4-烯酸或六-5-烯酸化合物的内酯化以及环己烯与不同羧酸的酯化反应均很容易进行，从而导致相应的胺化或氧化产物高达99％的孤立产量。初步的NMR实验和DFT计算表明，分子内加氢氨化反应是通过磺酰亚胺酸中间体（NS-OH）进行的，形成布朗斯台德酸HF或HBF 4的可能性较小。