cyclohexa-1,5-dienylmethyl benzoate

• 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: cyclohexa-1,5-dienylmethyl benzoate
• 英文别名: 2-(benzoyloxymethyl)-1,3-cyclohexadiene；Cyclohexa-1,5-dien-1-ylmethyl benzoate；cyclohexa-1,5-dien-1-ylmethyl benzoate
• 化学式: C₁₄H₁₄O₂
• 分子量: 214.264
• InChiKey: FULLNKFMBXXSDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  苯甲酰氯 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 cyclohexa-1,5-dienylmethyl benzoate
  参考文献：
  名称：

  2-SUBSTITUTED-1,3-CYCLOHEXADIENES BY INTERMOLECULAR, METHYLENE-FREE TANDEM ENYNE METATHESIS

  摘要：

  DOI：

  10.15227/orgsyn.083.0200

文献信息

• Cyclodimerization of Alkynes with Phosphine-Free Ruthenium Carbene Complexes:  Carbene Consumption by a Shunted Alkyne Oligomerization
  作者：Steven T. Diver、Amol A. Kulkarni、Daniel A. Clark、Brian P. Peppers

  DOI：10.1021/ja0705689

  日期：2007.5.1

  A new cyclodimerization of ruthenium carbenes and alkynes is reported. The cyclodimerization produces substituted cyclopentadienes and consumes the carbene complex. Cyclodimerization of alkynes is predominant at low alkene concentrations and was found to be competitive with enyne metathesis. The presence of the ortho alkyl ether in the ruthenium carbene complex appears to be a critical determinant

  报道了一种新的钌卡宾和炔烃的环二聚反应。环二聚反应产生取代的环戊二烯并消耗卡宾配合物。炔烃的环二聚在低烯烃浓度下占主导地位，并且发现与烯炔复分解具有竞争性。钌卡宾配合物中邻烷基醚的存在似乎是形成环戊二烯的关键决定因素。在较高的烯烃浓度下，观察到的环二聚反应可以被抑制，有利于烯炔复分解。
• Tandem dienyne cross-metathesis/ring-closing metathesis
  作者：Jason A Smulik、Steven T Diver

  DOI：10.1016/s0040-4039(00)01922-5

  日期：2001.1

  Tandem enyne cross-metathesis/ring-closing metathesis between terminal alkynes and 1,5-hexadiene has been demonstrated using the 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene-substituted ruthenium benzylidene complex. Synthesis of 2-substituted 1,3-cyclohexadienes using this one step tandem reaction is reported. In addition, metathesis products were subjected to [4+2] cycloaddition with N-methylmaleimide

  末端炔烃和1,5-己二烯之间的串联烯炔交叉复分解/闭环易位反应已使用1,3-二甲磺酰基-4,5-二氢咪唑-2-亚烷基取代的钌亚苄基络合物进行了证明。报道了使用这一一步串联反应合成2-取代的1，3-环己二烯。此外，在一个合成步骤中，将易位产物与N-甲基马来酰亚胺进行[4 + 2]环加成反应，得到相应的环加合物。
• Ring Synthesis by Stereoselective, Methylene-Free Enyne Cross Metathesis
  作者：Amol A. Kulkarni、Steven T. Diver

  DOI：10.1021/ja0476922

  日期：2004.7.1

  Tandem enyne metathesis between 1-alkynes and 1,5-cyclooctadiene or all-cis-1,4-polybutadiene resulted in a direct, one-step ring synthesis of cyclohexadienes by methylene-free metathesis. The use of methylene-free metathesis conditions provided apparent Z-selectivity in the intermolecular enyne metathesis step.
• Synthesis of 1,3-cyclohexadienes by tandem diene–alkyne metathesis: improved procedure
  作者：Mark D. Middleton、Steven T. Diver

  DOI：10.1016/j.tetlet.2005.04.017

  日期：2005.6

  A practical synthesis of 2-substituted 1,3-cyclohexadienes by the cross enyne metathesis between alkynes and 1,5-hexadiene is reported. The isolation of the 1,3-cyclohexadienes has been hampered by the formation of an inseparable triene by-product. The use of a second consecutive cross alkene metathesis to give water-soluble products allowed removal of this by-product. Using this one-pot procedure, a synthesis of cyclohexadienes from simple starting materials was developed. The procedure was used in a three-step synthesis of a functionalized tetrahydroquinoline using Pd(II)-catalyzed chloroacetoxyiation (Backvall reaction) for cyclohexadiene functionalization. (c) 2005 Elsevier Ltd. All rights reserved.