(cyclohexen-1-yl)methyl benzoyl ester

• 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: (cyclohexen-1-yl)methyl benzoyl ester
• 英文别名: cyclohex-1-en-1-ylmethyl benzoate；Cyclohexen-1-ylmethyl benzoate
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: GEVHDSVITZRIJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (+/-)-trans-N-(2-hydroxy)cyclohexylmethyl benzoate 在 6-氯嘌呤 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到(cyclohexen-1-yl)methyl benzoyl ester
  参考文献：
  名称：

  1,2-Disubstituted cyclohexane nucleosides: comparative study for the synthesis of cis and trans adenosine analogues

  摘要：

  A new class of adenosine analogues with 1,2-disubstituted carbocycles (with cis and trans stereochemistry) have been synthesized. Construction of the base on the amino group of (+/-)-cis-(2-aminocyclohexyl)methanol was more efficient than the Mitsunobu condensation between the purine base and protected (+/-)-trans-(2-hydroxymethyl)cyclohexanol. The latter strategy gave the final compound with cis stereochemistry in a short number of steps with the overall yield depending on the nature of the protecting group on the hydroxymethyl group of the diol. However, Mitsunobu condensation between a purine base and the protected (+/-)-cis-(2-hydroxymethyl)cyclohexanol is not an ideal method to obtain trans purine derivatives because the elimination reaction is faster than the substitution reaction. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.10.076

文献信息

• Tandem Catalysis: Transforming Alcohols to Alkenes by Oxidative Dehydroxymethylation
  作者：Xuesong Wu、Faben A. Cruz、Alexander Lu、Vy M. Dong

  DOI：10.1021/jacs.8b06069

  日期：2018.8.15

  a Rh-catalyst for accessing olefins from primary alcohols by a C-C bond cleavage that results in dehomologation. This functional group interconversion proceeds by an oxidation-dehydroformylation enabled by N, N-dimethylacrylamide as a sacrificial acceptor of hydrogen gas. Alcohols with diverse functionality and structure undergo oxidative dehydroxymethylation to access the corresponding olefins. Our

  我们报道了一种 Rh 催化剂，用于通过 CC 键断裂从伯醇中获取烯烃，从而导致脱同系反应。这种官能团互变通过 N,N-二甲基丙烯酰胺作为氢气的牺牲受体实现的氧化-脱氢甲酰化进行。具有不同官能度和结构的醇经过氧化脱羟甲基反应得到相应的烯烃。我们的催化剂方案能够实现 (+)-育亨苯酮的两步半合成和原料烯烃的脱同系。
• Normal Alpha Olefin Synthesis Using Dehydroformylation or Dehydroxymethylation
  申请人：Chevron Phillips Chemical Company LP

  公开号：US20190263729A1

  公开（公告）日：2019-08-29

  The present invention discloses processes for producing normal alpha olefins, such as 1-hexene, 1-octene, 1-decene, and 1-dodecene in a multistep synthesis scheme from another normal alpha olefin. Also disclosed are reactions for converting aldehydes, primary alcohols, and terminal vicinal diols into normal alpha olefins.

  本发明公开了一种从另一种正构α烯烃中通过多步合成方案生产正构α烯烃（如1-己烯、1-辛烯、1-癸烯和1-十二烯）的工艺。还公开了将醛、初级醇和末端邻二醇转化为正构α烯烃的反应。
• Oxidative Dehydroxymethylation of Alcohols to Produce Olefins
  申请人：The Regents of the University of California

  公开号：US20190262819A1

  公开（公告）日：2019-08-29

  Catalyst compositions for the conversion of aldehyde compounds and primary alcohol compounds to olefins are disclosed herein. Reactions include oxidative dehydroxymethylation processes and oxidative dehydroformylation methods, which are beneficially conducted in the presence of a sacrificial acceptor of H 2 gas, such as N,N-dimethylacrylamide.

  本文揭示了用于将醛类化合物和一次醇类化合物转化为烯烃的催化剂组合物。反应包括氧化脱羟甲基化过程和氧化脱甲基醛化方法，在存在H2气体的牺牲性受体（如N,N-二甲基丙烯酰胺）的情况下有益地进行。
• Copper-catalyzed regioselective allylic oxidation of olefins via C–H activation
  作者：Nengbo Zhu、Bo Qian、Haigen Xiong、Hongli Bao

  DOI：10.1016/j.tetlet.2017.09.047

  日期：2017.10

  A regioselective oxidation of allylic C–H bond to C–O bond catalyzed by copper (I) was developed with diacyl peroxides as oxidants. The oxidation of allylic C–H bond was accomplished with good yield and regioselectivity under mild reaction conditions. This method has a broad substrate scope including cyclic olefins, terminal and internal acyclic olefins and allyl benzene compounds. The reaction proceeds

  以二酰基过氧化物为氧化剂，开发了由铜（I）催化的烯丙基CH键至CH键的区域选择性氧化。在温和的反应条件下，烯丙基CH键的氧化反应具有良好的收率和区域选择性。该方法具有广泛的底物范围，包括环烯烃，末端和内部无环烯烃以及烯丙基苯化合物。如自旋俘获实验所建议的，反应是通过自由基机理进行的。
• Normal alpha olefin synthesis using dehydroformylation or dehydroxymethylation
  申请人：Chevron Phillips Chemical Company LP

  公开号：US10723672B2

  公开（公告）日：2020-07-28

  The present invention discloses processes for producing normal alpha olefins, such as 1-hexene, 1-octene, 1-decene, and 1-dodecene in a multistep synthesis scheme from another normal alpha olefin. Also disclosed are reactions for converting aldehydes, primary alcohols, and terminal vicinal diols into normal alpha olefins.

  本发明公开了以多步骤合成方案从另一种正α烯烃生产正α烯烃（如 1-己烯、1-辛烯、1-癸烯和 1-十二烯）的工艺。此外，还公开了将醛、伯醇和末端邻位二元醇转化为正常α-烯烃的反应。