1,2-diphenylcyclohexa-1,4-diene | 17351-29-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,2-diphenylcyclohexa-1,4-diene
• 英文别名: (2-Phenylcyclohexa-1,4-dien-1-yl)benzene
• CAS: 17351-29-0
• 化学式: C₁₈H₁₆
• 分子量: 232.325
• InChiKey: IURVNQRMBGAZRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,2-diphenylcyclohexa-1,4-diene 在 溶剂黄146 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 反应 0.5h， 以86%的产率得到邻三联苯
  参考文献：
  名称：

  Novel Ene Trimerization of 1-Phenylcyclopropene

  摘要：

  1-Phenylcyclopropene (1) was synthesized by treatment of 1,1,2-tribromo-2-phenylcyclopropane (2) with 2.5 equiv of methyllithium followed by protonation. Compound 1 underwent ene dimerization to form ene dimer 5 followed by ene reaction with monomer 1 (enophile) to give an ene trimer 6. Both of these two ene reactions derived endo transition states. In the meantime, the [2+2] adduct, trans1,2-diphenylbicyclo[3.1.0.0(2,4)]hexane (7), was also formed. When the adduct 7 was heated at THF refluxing temperature, 1,2-diphenylcyclohexa-1,4-diene (8) was obtained. Compound 8 was treated with DDQ to yield o-diphenylbenzene.

  DOI：

  10.1021/jo048889f
• 作为产物：
  描述：

  2-苯基-1-乙炔硼酸频那醇酯 在 Grubbs catalyst first generation 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 正丁基锂 、 二氯二茂锆 、 三丁基膦 、 sodium hydroxide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 27.0h， 生成 1,2-diphenylcyclohexa-1,4-diene
  参考文献：
  名称：

  Synthesis of Cyclic 1-Alkenylboronates via Zr-Mediated Double Functionalization of Alkynylboronates and Sequential Ru-Catalyzed Ring-Closing Olefin Metathesis

  摘要：

  Synthesis of novel cyclic 1-alkenylboronates is accomplished through the zirconium-mediated regio- and stereoselective double functionalization of 1-alkynylboronates and the subsequent ruthenium-catalyzed ring-closing metathesis (RCM). The obtained substituted cyclic 1-alkenylboronates are transformed into o-terphenyl and triphenylene derivatives.

  DOI：

  10.1021/ol400896u

文献信息

• Stereoselective construction of 3a-methylhydrindanes starting from 2,7-enynol derivatives based on Ti(II)-mediated cyclization and Ru-catalyzed ring-closing metathesis
  作者：Mutsumi Ohkubo、Wataru Uchikawa、Hitomi Matsushita、Aiko Nakano、Takayuki Shirato、Sentaro Okamoto

  DOI：10.1016/j.tetlet.2006.05.030

  日期：2006.7

  The Ti(II)-mediated cyclization of 3-methyloct-2-en-7-yn-l-ol derivatives 2 proceeded stereoselectively to afford 1-methyl-2-(1-alkylbut-3-enylidene)-1-vinylcyclopentanes 3 after treatment of the resulting alkenyltitaniums with allylbromide in the presence of CuCN, which was readily converted to 3a-methyl-2,3,3a,6-tetrahydro-1H-indenes 1 by the Ru-catalyzed ring-closing metathesis. (c) 2006 Elsevier Ltd. All rights reserved.
• Novel Ene Trimerization of 1-Phenylcyclopropene
  作者：Gon-Ann Lee、Chih-Yi Chang

  DOI：10.1021/jo048889f

  日期：2004.12.1

  1-Phenylcyclopropene (1) was synthesized by treatment of 1,1,2-tribromo-2-phenylcyclopropane (2) with 2.5 equiv of methyllithium followed by protonation. Compound 1 underwent ene dimerization to form ene dimer 5 followed by ene reaction with monomer 1 (enophile) to give an ene trimer 6. Both of these two ene reactions derived endo transition states. In the meantime, the [2+2] adduct, trans1,2-diphenylbicyclo[3.1.0.0(2,4)]hexane (7), was also formed. When the adduct 7 was heated at THF refluxing temperature, 1,2-diphenylcyclohexa-1,4-diene (8) was obtained. Compound 8 was treated with DDQ to yield o-diphenylbenzene.
• Oligomerization catalysts. III. Cyclocodimerization of conjugated dienes with acetylenic hydrocarbons catalyzed by iron(0) complexes. Synthesis of 1,2-diphenyl-1,4-cyclohexadiene
  作者：Antonio Carbonaro、Alberto Greco、Gino Dall'Asta

  DOI：10.1021/jo01274a061

  日期：1968.10
• 2,7-Diphenyloxepin
  作者：Michael J. McManus、Glenn A. Berchtold、Derek R. Boyd、Deirdre A. Kennedy、John Malone

  DOI：10.1021/jo00364a031

  日期：1986.7
• MCMANUS M. J.; BERCHTOLD G. A.; BOYD D. R.; KENNEDY D. A.; MALONE J. F., J. ORG. CHEM., 51,(1986) N 14, 2784-2787
  作者：MCMANUS M. J.、 BERCHTOLD G. A.、 BOYD D. R.、 KENNEDY D. A.、 MALONE J. F.

  DOI：——

  日期：——