(Z)-1-(4-chlorophenyl)-1-hexene | 144758-47-4

• 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: (Z)-1-(4-chlorophenyl)-1-hexene
• 英文别名: 1-chloro-4-[(Z)-hex-1-enyl]benzene
• CAS: 144758-47-4
• 化学式: C₁₂H₁₅Cl
• 分子量: 194.704
• InChiKey: XIMFWOHZHWFFOG-WAYWQWQTSA-N

物化性质

• 沸点：
  272.8±9.0 °C(Predicted)
• 密度：
  1.014±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  (Z)-1-(4-chlorophenyl)-1-hexene 在 Hoveyda-Grubbs catalyst second generation 、 sodium formate 作用下， 以 甲苯 为溶剂， 以65%的产率得到(E)-1-chloro-4-(hex-1-en-1-yl)benzene
  参考文献：
  名称：

  From trials on rosuvastatin production waste valorization to development of new catalytic methods for Z → E isomerization of alkenes

  摘要：

  A convenient method for Z → E geometry isomerization of aryl–aryl (stilbenes), alkyl–aryl, and alkyl–alkyl alkenes was developed.

  DOI：

  10.1039/d3nj05865d
• 作为产物：
  描述：

  4-氯苯乙炔 在 sodium hydroxide 、 碲化氢 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 26.25h， 生成 (Z)-1-(4-chlorophenyl)-1-hexene
  参考文献：
  名称：

  Tellurium in Organic Synthesis. Preparation of Z-Vinylic Cuprates from Z-Vinylic Tellurides and Their Reaction with Enones and Epoxides

  摘要：

  Z-Vinylic tellurides, obtained with 100% stereoselectivity by the hydrotelluration of acetylenes, are easily transformed into Z-vinylic higher order cyanocuprates by reaction with preformed Me(2)Cu(CN)Li-2, n-Bu(2)Cu(CN)Li-2, or n-Bu(2-Th)Cu(CN)Li-2, with total retention of the double-bond configuration. The resulting vinylic higher order cyanocuprates react with unhindered enones to give the corresponding 1,4-addition products in good yields. Reaction of the vinylic higher order cyanocuprates with monosubstituted epoxides at 0 degrees C gives the homoallylic alcohols resulting from the attack to the less-substituted carbon atom, while the disubstituted epoxides failed to react. Allylic epoxides react at -78 degrees C with the vinylic higher order cyanocuprates to give mixtures of 1,2- and 1,4-opening products, the 1,4-product predominating. In all cases the double-bond configuration of the original vinylic telluride was preserved. The vinylic cuprates derived from simple vinylic tellurides and conjugated 1-telluroenynes react with epoxides at 0 degrees C, while vinylic cuprates derived from conjugated 1-tellurodienes required the addition of 1 equiv of BF3 . Et(2)O to give the homoallylic alcohols on reaction with epoxides. The opening of optically pure epoxides through tellurium/copper transmetalation is stereospecific, giving one single stereoisomer of the corresponding homoallylic alcohol.

  DOI：

  10.1021/jo951547c

文献信息

• 1-Methyl-1H-tetrazol-5-yl (MT) sulfones in the Julia-Kocienski olefination: Comparison with the PT and the TBT sulfones
  作者：Kaori Ando、Daiki Kawano、Daiki Takama、Yutaka Semii

  DOI：10.1016/j.tetlet.2019.05.007

  日期：2019.6

  n-pentyl 1-methyl-1H-tetrazol-5-yl (MT) sulfone 1a in the Julia-Kocienski reactions were compared with those of the PT sulfone 1b and the TBT sulfone 1c. The improved stability of the anion derived from the n-pentyl MT sulfone 1a enhanced the efficiency of the olefination reactions and gave higher yields of the product alkenes 3 compared with the PT sulfone 1b. Especially high E-selectivity and high

  比较了新制备的正戊基1-甲基-1 H-四唑-5-基（MT）砜1a在Julia-Kocienski反应中的稳定性和立体选择性，与PT砜1b和TBT砜1c的稳定性和立体选择性进行了比较。与PT砜1b相比，由正戊基MT砜1a衍生的阴离子的稳定性提高，提高了烯化反应的效率，并提高了烯烃3的产率。从与芳族醛和α，β-不饱和醛的反应中获得特别高的E-选择性和高产率。的选择性与PT砜1b相比，1a对碱抗衡离子的变化不太敏感。具有乙基或更长烷基链的MT砜的反应也以高收率选择性地产生了E-烯烃。
• Influence of the gegenion in the transmetalation reaction of vinylic tellurides with higher order cyanocuprates
  作者：André Chieffi、João V. Comasseto

  DOI：10.1016/s0040-4039(00)73112-1

  日期：1994.6

  Dilithium cyanocuprates R2LCu(CN)Li2 (L=2-Th, Me) react with vinylic tellurides of Z configuration, RCHCHTeR1 to give higher order vinylic cyanocuprates, [(RCHCH)LCu(CN)Li2]. By changing the gegenion from lithium to magnesium [R2LCu(CN)LiMgBr or R2LCu(CN)(MgBr)2] the reaction gives cross - coupling products of Z configuration, RCHCHR2 in good yields.

  二锂cyanocuprates - [R 2 LCU（CN）栗2（L = 2-Th时，Me）的具有乙烯型碲化物反应Ž配置，RCHCHTeR 1得到高阶乙烯基cyanocuprates，[（RCHCH）LCU（CN）栗2 ]。通过将锗酸根离子从锂变为镁[R 2 LCu（CN）LiMgBr或R 2 LCu（CN）（MgBr）2 ]，该反应以良好的收率得到了Z构型的交联产物RCH = CHR 2。
• Ir-Catalyzed Distal Branch-Selective Hydroarylation of Unactivated Internal Alkenes with Benzanilides via C–H Activation along with Consecutive Isomerization
  作者：King Hung Nigel Tang、Ryo Tokutake、Mamoru Ito、Takanori Shibata

  DOI：10.1021/acs.orglett.3c01619

  日期：2023.7.21

  We herein report a synergistic strategy of C–H activation and consecutive isomerization catalyzed by an Ir catalyst to selectively obtain branched isomers as C–H alkylated products of benzanilide derivatives. A well-tuned ligand and a directing group are crucial to achieve this selectivity. The scope of this reaction is demonstrated by the use of a variety of substituents and complex molecules.

  我们在此报告了一种由Ir催化剂催化的C-H活化和连续异构化的协同策略，以选择性地获得支化异构体作为苯甲酰苯胺衍生物的C-H烷基化产物。良好调节的配体和导向基团对于实现这种选择性至关重要。该反应的范围通过使用各种取代基和复杂分子来证明。
• Higher order vinyl cyanocuprates from vinylic tellurides
  作者：Fábio C. Tucci、André Chieffi、João V. Comasseto

  DOI：10.1016/0040-4039(92)89015-5

  日期：1992.9

  Bis-vinylic tellurides, 1-tellurodienes, 1-telluroenynes and vinyl thienyl tellurides react with higher order cyanocuprates giving the corresponding higher order vinyl cyanocuprates with retention of the olefine geometry.