1-(2-(2-(but-3-enyl)-2-phenylcyclopropylidene)-1-(4-chlorophenyl)vinyl)-4-chlorobenzene | 1201909-59-2

• 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: 1-(2-(2-(but-3-enyl)-2-phenylcyclopropylidene)-1-(4-chlorophenyl)vinyl)-4-chlorobenzene
• CAS: 1201909-59-2
• 化学式: C₂₇H₂₂Cl₂
• 分子量: 417.378
• InChiKey: JWIFYCPATCFILY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 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-(2-(but-3-enyl)-2-phenylcyclopropylidene)-1-(4-chlorophenyl)vinyl)-4-chlorobenzene 在 di(rhodium)tetracarbonyl dichloride 、 一氧化碳 作用下， 以 甲苯 、 乙腈 为溶剂， 100.0 ℃ 、101.33 kPa 条件下， 反应 2.0h， 以75%的产率得到6-(bis(4-chlorophenyl)methylene)-1-phenylbicyclo[5.1.0]oct-3-ene
  参考文献：
  名称：

  Rhodium(I)-Catalyzed Intramolecular Ene Reaction of Vinylidenecyclopropanes and Alkenes for the Formation of Bicyclo[5.1.0]octylenes

  摘要：

  An efficient catalytic system for the intramolecular ene reaction of allene and alkene of diarylvinylidenecyclopropanes has been established. The reaction was achieved by using [RhCl(CO)(2)](2) as the catalyst In co-solvents of toluene and acetonitrile. MeCN was found to play a crucial role in controlling the reaction toward formation of bicyclo[5.1.0]octylene derivatives. An alternative system consisting of [RhCl(CO)(2)](2) and toluene in the absence of MeCN was found to give [2 + 2] cycloaddition adducts. The structures have been unambiguously determined by X-ray structural analysis. Deuterium labeling experiments were conducted to confirm the mechanism hypothesis.

  DOI：

  10.1021/ol902505p
• 作为产物：
  描述：

  1-氯-4-[1-(4-氯苯基)乙烯基]苯 在 potassium tert-butylate 、 四丁基硫酸氢铵 、 sodium hydroxide 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 36.0h， 生成 1-(2-(2-(but-3-enyl)-2-phenylcyclopropylidene)-1-(4-chlorophenyl)vinyl)-4-chlorobenzene
  参考文献：
  名称：

  Halogenation Reagents Initiating Ring Opening of Vinylidenecyclopropanes: Easy Access to Halogenated Tetrahydropyrans

  摘要：

  一种新的合成策略被开发出来，使用卤素化试剂（NBS、NIS和selectfluor）来启动与含有醇基链的二芳基乙烯基环丙烷（VDCPs）相关的环内开环反应。该方法在温和条件下提供了多种卤化四氢呱衍生物，产率中等至良好。基于先前的文献，提出了合理的反应机制，并仔细研究了底物范围。

  DOI：

  10.1055/s-0030-1259715

文献信息

• Reactions of Vinylidenecyclopropanes with Diphenyl Diselenide in the Presence of AIBN and Thermally-Induced Further Transformations
  作者：Wei Yuan、Yin Wei、Min Shi、Yuxue Li

  DOI：10.1002/chem.201103461

  日期：2012.1.27

  vinylidenecyclopropanes with diphenyl diselenide in the presence of AIBN and upon heating gives the corresponding bicyclo[3.1.0]hexane derivatives in good yields. These compounds undergo thermal‐induced radical 1,4‐hydrogen shifts through a ring‐opening pathway of allylic cyclopropane to give the corresponding cyclohexene derivatives stereoselectively in good yields at 200 °C (see scheme).

  自由基变换器：在AIBN存在下并加热后，将亚乙烯基环丙烷与二苯二硒化物化学转化，得到高收率的相应双环[3.1.0]己烷衍生物。这些化合物通过烯丙基环丙烷的开环途径经历热诱导的自由基1,4-氢转移，从而在200°C下以良好的产率立体选择性地生成相应的环己烯衍生物（参见方案）。
• Au/Ag-Catalyzed Intramolecular Ring-Opening of Vinylidene-cyclopropanes (VDCPs): An Easy Access to Functional Tetrahydropyrans
  作者：Wei Li、Wei Yuan、Surech Pindi、Min Shi、Guigen Li

  DOI：10.1021/ol902832s

  日期：2010.3.5

  An intramolecular ring-opening of vinylidenecyclopropanes (VDCPs) tethered with alcohol chains has been established. A series of transition metal catalysts and their combinations have been screened under mild conditions, and a cocatalyst system consisting of [(Ph3PAu)(3)O]BF4 (4 mol %) and AgOTf (4 mol %) was found to catalyze the reaction to completion within 10-30 min in 1,4-dioxane at 60 degrees C to give allene-functionalized tetrahydropyrans.