cyclohex-2-en-1-yl 3-methoxybenzoate | 1390625-62-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: cyclohex-2-en-1-yl 3-methoxybenzoate
• CAS: 1390625-62-3
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: BNUDZDUHAVKMJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  环己烷 、 3-甲氧基苯甲酸 在 (tetraphenylporphyrin)copper(II) 、 二叔丁基过氧化物 作用下， 反应 12.0h， 以89%的产率得到cyclohex-2-en-1-yl 3-methoxybenzoate
  参考文献：
  名称：

  铜卟啉催化烷烃与羧酸的交叉脱氢偶联：酯化和脱羧双途径

  摘要：

  首次报道了羧酸与烷烃的双功能铜卟啉催化交叉脱氢偶联（CDC）。根据羧酸底物，该反应产生烯丙基酯或烷基烯烃。铜卟啉催化CDC法具有反应时间短、官能团耐受性好、无碱、无溶剂、原子经济地生产目标产物等优点。

  DOI：

  10.1016/j.tet.2021.132377

文献信息

• Copper porphyrin as efficient catalysts for esterification of allyl sp3 C H bond with carboxylic acid
  作者：Ming-Feng Xiong、Atif Ali、Waseem Akram、Hao Zhang、Li-Ping Si、Hai-Yang Liu

  DOI：10.1016/j.catcom.2019.04.001

  日期：2019.5

  We described that copper 5,10,15,20-tetrakis (ethoxycarbonyl)porphyrin (TECP) catalyzed oxidative cross dehydrogenative coupling of allyl sp3 CH bond with acid for the synthesis of allyl esters in a homogeneous system. This reaction proceeded with broad substrate scope and good functional group tolerance. In the gram-level test, the turnover number (TON) reached to 8100 at 0.01 mol% catalyst loading

  我们描述了5,10,15,20-四（乙氧基羰基）卟啉铜（TECP）催化烯丙基sp 3 C H键与酸的氧化交叉脱氢偶联，用于在均相系统中合成烯丙基酯。该反应在宽的底物范围和良好的官能团耐受性下进行。在克级测试中，在催化剂负载量为0.01 mol％时，周转率（TON）达到8100，产率为81％。
• Copper Porphyrin Catalyzed C(sp3)–H Activation via Cross-Dehydrogenative Coupling: Facile Transformation of Aldehydes to Esters
  作者：Hai-Yang Liu、Gao-Qing Yuan、Zi-Wei Shan、Xiao-Yan Chen、Hao Zhang

  DOI：10.1055/a-1813-4235

  日期：2022.7

  catalyzed alkane C–H bond functionalization with aldehydes via cross-dehydrogenative coupling (CDC) using DTBP oxidant has been firstly described in nonsolvents or nonadditives system. Different aryl/heteroaryl carboxylic esters were obtained in good to excellent yields depending on the aldehyde derivatives. This CDC reaction catalyzed by copper porphyrin has the advantages of shorter reaction time, lower reaction

  铜卟啉通过使用 DTBP 氧化剂的交叉脱氢偶联 (CDC) 催化烷烃 C-H 键功能化与醛类首次在非溶剂或非添加剂体系中得到描述。取决于醛衍生物，以良好至优异的产率获得了不同的芳基/杂芳基羧酸酯。这种铜卟啉催化的CDC反应具有反应时间短、反应温度低、催化剂负载量小、反应气氛好氧等优点。
• Cu(II)/TBAI-Catalyzed Esterification of Acid Hydrazides via C(sp3)–H Oxidative Coupling
  作者：Guifeng Liu、Can Jin、Guomin Wu

  DOI：10.1055/s-0034-1379478

  日期：——

  A Cu2+/TBAI-cocatalyzed allylic ester synthesis was developed, which allows a direct coupling of acid hydrazides and cycloalkanes. This process makes use of commercially available, inexpensive, and abundant starting materials. Based on the extensive experimental data, a plausible radical mechanism was suggested.
• Cu-Catalyzed C(sp³)–H Bond Activation Reaction for Direct Preparation of Cycloallyl Esters from Cycloalkanes and Aromatic Aldehydes
  作者：Jincan Zhao、Hong Fang、Jianlin Han、Yi Pan

  DOI：10.1021/ol5009119

  日期：2014.5.2

  Cu-catalyzed dehydrogenation-olefination and esterification of C(sp(3))-H bonds of cycloalkanes with TBHP as an oxidant has been developed. The reaction involves four C-H bond activations and gives cycloallyl ester products directly from cycloalkanes and aromatic aldehydes.