6-phenyl-cyclohexa-1,3-dienecarboxylic acid methyl ester | 86601-60-7

• 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: 6-phenyl-cyclohexa-1,3-dienecarboxylic acid methyl ester
• 英文别名: methyl 6-phenylcyclohexa-1,3-dienecarboxylate；methyl 1,6-dihydro-[1,1'-biphenyl]-2-carboxylate；methyl 6-phenylcyclohexa-1,3-diene-1-carboxylate
• CAS: 86601-60-7
• 化学式: C₁₄H₁₄O₂
• 分子量: 214.264
• InChiKey: JPINZLVQISJFMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 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：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  苯甲醛 在 potassium tert-butylate 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 0.5h， 生成 6-phenyl-cyclohexa-1,3-dienecarboxylic acid methyl ester
  参考文献：
  名称：

  Oxygenative and Dehydrogenative [3 + 3] Benzannulation Reactions of α,β-Unsaturated Aldehydes and γ-Phosphonyl Crotonates Mediated by Air: Regioselective Synthesis of 4-Hydroxybiaryl-2-carboxylates

  摘要：

  Regioselective synthesis of 4-hydroxybiphenyl-2-carboxylates via the base-mediated oxygenative [3 + 3] benzannulation reaction of alpha,beta-unsaturated aldehydes and gamma-phosphonyl crotonates is reported. A hydroxyl group is installed in the final product on the originally phosphorus-bound carbon via a novel oxygenative and dehydrogenative transformation. The reaction proceeds rapidly in an open flask, uses atmospheric oxygen as an oxidant, and affords good yields of substituted biaryl phenols.

  DOI：

  10.1021/acs.orglett.6b00016

文献信息

• Tandem Michael addition/ylide olefination reaction for the synthesis of highly functionalized cyclohexadiene derivatives
  作者：Long-Wu Ye、Xun Han、Xiu-Li Sun、Yong Tang

  DOI：10.1016/j.tet.2008.06.048

  日期：2008.8

  A tandem Michael addition/ylide olefination for the rapid creation of highly functionalized cyclohexadiene is developed. The tandem annulation reactions afford versatile cyclohexadienes in good to excellent isolated yields. This method has been successfully applied to the synthesis of three biologically active molecules.

  开发了用于快速生成高度官能化环己二烯的串联迈克尔加成/叶立德烯化。串联环化反应以良好至优异的分离产率提供多功能环己二烯。该方法已成功应用于三种生物活性分子的合成。
• Regioselective synthesis of substituted cyclohexa-1,3-dienes via the base-mediated cyclisation of α,β-unsaturated carbonyl compounds and γ-phosphonylcrotonates
  作者：Prabhakar R. Joshi、Rajesh Chandra、Rajeev S. Menon

  DOI：10.1016/j.tetlet.2020.152380

  日期：2020.9

  The base-mediated reaction of α,β-unsaturated carbonyl compounds and γ-phosphonylcrotonates under an argon atmosphere readily furnishes substituted cyclohexa-1,3-dienes. The cyclisation proceeds with complete regioselectivity to afford products that are readily amenable to further redox manipulations. The presented method allows the rapid and regioselective syntheses of six-membered carbocycles at

  在氩气氛下，α，β-不饱和羰基化合物与γ-膦酰基巴豆酸酯的碱介导反应很容易提供取代的环己-1,3-二烯。环化以完全的区域选择性进行，以提供易于进行进一步的氧化还原操纵的产物。所提出的方法允许在三个不同的氧化水平下快速和区域选择性地合成六元碳环。
• OIDA, TATSUO;TANIMOTO, SHIGEO;IKEHIRA, HIDEYUKI;OKANO, MASAYA, BULL. INST. CHEM. RES. KYOTO UNIV., 1982, 60, N 5-6, 336-341
  作者：OIDA, TATSUO、TANIMOTO, SHIGEO、IKEHIRA, HIDEYUKI、OKANO, MASAYA

  DOI：——

  日期：——