3-Oxo-cyclohex-1-enecarboxylic acid benzyl ester | 124693-24-9

• 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: 3-Oxo-cyclohex-1-enecarboxylic acid benzyl ester
• 英文别名: Benzyl 3-oxocyclohexene-1-carboxylate
• CAS: 124693-24-9
• 化学式: C₁₄H₁₄O₃
• 分子量: 230.263
• InChiKey: UZQFGWAZWLHFCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  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：
  0.29
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Oxo-cyclohex-1-enecarboxylic acid benzyl ester 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium hydride 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 11.0h， 生成 benzyl 3-cycloheptenecarboxylate
  参考文献：
  名称：

  Ring expansion reactionsvia endocyclic cleavage of cyclopropylcarbinyl radicals

  摘要：

  Ring expansion reactions via endocyclic cleavage of cyclopropylcarbinyl radicals are described. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00507-9
• 作为产物：
  描述：

  3-(tert-Butyl-dimethyl-silanyloxy)-cyclohexa-1,3-dienecarboxylic acid benzyl ester 在 四丁基氟化铵 作用下， 生成 3-Oxo-cyclohex-1-enecarboxylic acid benzyl ester
  参考文献：
  名称：

  Ring expansion reactionsvia endocyclic cleavage of cyclopropylcarbinyl radicals

  摘要：

  Ring expansion reactions via endocyclic cleavage of cyclopropylcarbinyl radicals are described. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00507-9

文献信息

• (+)-Camphor Derivative Induced Asymmetric [2 + 2] Photoaddition Reaction
  作者：Guolei Zhao、Chao Yang、Hongnan Sun、Run Lin、Wujiong Xia

  DOI：10.1021/ol203314y

  日期：2012.2.3

  An efficient approach to construct an enantiomerically pure cyclobutane skeleton by means of the chiral auxiliary induced [2 + 2] photoaddition reactions has been described. This asymmetric photoreaction exhibited high diastereoselectivity and provided the photoadducts in excellent yields.

  已经描述了通过手性助剂诱导的[2 + 2]光加成反应构建对映体纯的环丁烷骨架的有效方法。这种不对称的光反应表现出高的非对映选择性，并以优异的产率提供了光加合物。
• Regiospecific synthesis of a bridgehead-functionalized bicyclo[2.2.2]octenone
  作者：Andrew S. Kende、Jiong Lan、Dorit Arad

  DOI：10.1016/s0040-4039(02)01065-1

  日期：2002.7

  Three independent strategies are tested toward the synthesis of the protected 1-aminobicyclo[2.2.2]octene ketodiester 1. One of these three is found to be completely regioselective. It proceeds by Diels-Alder addition of dimethyl acetylenedicarboxylate to the silyl enol ether of 3-benzyloxycarbonyl-2-cyclohexenone, followed by a chemoselective Curtius rearrangement. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Ring expansion reactionsvia endocyclic cleavage of cyclopropylcarbinyl radicals
  作者：Phil Ho Lee、Byungcheol Lee、Jukyoung Lee、Seung Ki Park

  DOI：10.1016/s0040-4039(99)00507-9

  日期：1999.4

  Ring expansion reactions via endocyclic cleavage of cyclopropylcarbinyl radicals are described. (C) 1999 Elsevier Science Ltd. All rights reserved.