1-chloro-4-(hexa-1,5-dien-2-yl)benzene | 65912-75-6

• 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-chloro-4-(hexa-1,5-dien-2-yl)benzene
• 英文别名: 1-Chloro-4-hexa-1,5-dien-2-ylbenzene
• CAS: 65912-75-6
• 化学式: C₁₂H₁₃Cl
• 分子量: 192.688
• InChiKey: DZPGRIMQAOYYMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 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-chloro-4-(hexa-1,5-dien-2-yl)benzene 在 (-)-bis(neomenthylindenyl)zirconium dichloride 、 氧气 作用下， 以 二氯甲烷 为溶剂， 反应 97.0h， 生成 ((1R,3R)-1-(4-chlorophenyl)-3-ethylcyclopentyl)methanol
  参考文献：
  名称：

  锆催化双碳铝催化不对称合成具有全碳四元立体中心的手性环戊烷

  摘要：

  全碳四元立体中心：各种未活化的1,5-二烯经锆催化的双碳铝键合可通过形成两个新的C-C键，有效地利用两个立体中心（包括一个全碳四元立体中心）有效地接触手性环戊烷作为具有高非对映选择性和对映选择性的C-Al键。

  DOI：

  10.1002/anie.201706198
• 作为产物：
  描述：

  4-氯苯甲酰氯 在 copper(l) iodide 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 1-chloro-4-(hexa-1,5-dien-2-yl)benzene
  参考文献：
  名称：

  钯催化1,5-二烯的羰基化环化

  摘要：

  已经开发了一种新颖的，原子经济的钯催化的1,5-二烯到2-亚烷基环戊烷酮的异构化-羰基化环化反应，它为具有高立体选择性的2-亚烷基环戊烷酮提供了一种快速而直接的方法。发现该反应通过烯烃异构化和选择性的烃基化环化进行，以产生具有高选择性的2-亚烷基环戊酮。

  DOI：

  10.1021/acs.orglett.9b02230

文献信息

• Halogenation Reagents Initiating Ring Opening of Vinylidenecyclopropanes: Easy Access to Halogenated Tetrahydropyrans
  作者：Min Shi、Wei Yuan

  DOI：10.1055/s-0030-1259715

  日期：2011.4

  A novel synthetic protocol that uses halogenation reagents (NBS, NIS and selectfluor) to initiate intramolecular ring-opening reactions of diarylvinylidenecyclopropanes (VDCPs) connected to alcohol-bearing chains has been developed. The approach provides a variety of halogenated tetrahydropyran derivatives in moderate to good yields under mild conditions. Plausible reaction mechanisms are proposed on the basis of previous literature and the substrate scope has been carefully examined.

  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。
• 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）。
• Rates of the Cope rearrangement of some 2-aryl-1,5-hexadienes
  作者：Elliot N. Marvell、Thomas H. C. Li

  DOI：10.1021/ja00471a037

  日期：1978.2
• Rhodium(I)-Catalyzed Intramolecular Ene Reaction of Vinylidenecyclopropanes and Alkenes for the Formation of Bicyclo[5.1.0]octylenes
  作者：Wei Li、Wei Yuan、Min Shi、Erik Hernandez、Guigen Li

  DOI：10.1021/ol902505p

  日期：2010.1.1

  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.
• 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.