(Z)-hept-2-en-2-ylbenzene | 83021-59-4

• 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)-hept-2-en-2-ylbenzene
• 英文别名: [(1Z)-1-methyl-1-hexenyl]benzene；[(Z)-hept-2-en-2-yl]benzene
• CAS: 83021-59-4
• 化学式: C₁₃H₁₈
• 分子量: 174.286
• InChiKey: QXMFUURXCNDYJZ-XFXZXTDPSA-N

物化性质

• 沸点：
  244.0±7.0 °C(Predicted)
• 密度：
  0.872±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：
  0.38
• 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)-hept-2-en-2-ylbenzene 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到3-butyl-2-methyl-2-phenyloxirane
  参考文献：
  名称：

  Isomerization of Terminal Epoxides by a [Pd–H] Catalyst: A Combined Experimental and Theoretical Mechanistic Study

  摘要：

  An unusual palladium hydride complex has been shown to be a competent catalyst in the isomerization of a variety of terminal and internal epoxides. The reaction displayed broad scope and synthetic utility. Experimental and theoretical evidence are provided for an unprecedented hydride mechanism characterized by two distinct enantio-determining steps. These results hold promise for the development of an enantioselective variant of the reaction.

  DOI：

  10.1021/ja400325w
• 作为产物：
  描述：

  (1R_P*,3′S*,4′R*)-3′-buthyl-4′-methyl-1,4′-diphenyl-1H-spiro[2,1-benzazaphosphole-1,2′-[1,2]oxaphosphetan]-3(2H)-one 以 氘代二甲亚砜 为溶剂， 反应 12.0h， 以94%的产率得到(Z)-hept-2-en-2-ylbenzene
  参考文献：
  名称：

  不稳定和半稳定的磷叶立德衍生物的螺[1,2]氧杂磷杂环戊烷：它们的合成，动力学和计算研究

  摘要：

  通过稳定的一系列三和四取代的螺- oxaphosphetanes的邻-苯甲酰胺（Ò BA）和ñ -甲基邻-苯甲酰胺（M ö BA）配位体已经由C的反应，合成α，C邻-dilithiated磷腈与醛和酮。它们包括对映体纯产物和在环的C 3处具有苯基取代基的分离的氧杂膦烷的第一个实例。对它们的热分解的动力学研究表明，在电子，[1,2]，[1,3]空间和溶剂效应的影响下，该过程通过极性过渡态（ρ= -0.22）不可逆地发生，C3 / P- [1,2]相互作用是对Δ的最大贡献ģ ⧧烯的。在许多情况下已经观察到通过立体突变使磷构型反转。DFT计算表明，o BA衍生物通过分离的（N，O）（Ph，C 6 H 4，C）氧代磷杂环戊烷（通道A）烯化，而M o BA化合物则通过异构体（C 6 H 4，O）分解得更快由涉及M B2的P-立体突变形成的（C，N，Ph）排列机制（渠道B）。P-异构化的能垒低于烯化的

  DOI：

  10.1021/acs.joc.0c01270

文献信息

• Cobalt-Catalyzed Regioselective Dehydrohalogenation of Alkyl Halides with Dimethylphenylsilylmethylmagnesium Chloride
  作者：Tsuneyuki Kobayashi、Hirohisa Ohmiya、Hideki Yorimitsu、Koichiro Oshima

  DOI：10.1021/ja804277x

  日期：2008.8.27

  dimethylphenylsilylmethylmagnesium chloride result in highly regioselective dehydrohalogenation. The reaction does not follow the conventional E2 elimination mechanism but includes beta-hydride elimination from the corresponding alkylcobalt intermediate. The interesting reaction mechanism of the cobalt-catalyzed dehydrohalogenation offered unique transformations that are otherwise difficult to attain.

  卤代烷烃与二甲基苯基甲硅烷基甲基氯化镁的钴催化反应导致高度区域选择性的脱卤化氢。该反应不遵循传统的 E2 消除机制，但包括从相应的烷基钴中间体中消除 β-氢化物。钴催化脱卤化氢的有趣反应机制提供了否则难以实现的独特转化。
• Polymer-bound palladium-catalyzed cross-coupling of organoboron compounds with organic halides and organic triflates
  作者：Su-Bum Jang

  DOI：10.1016/s0040-4039(97)00171-8

  日期：1997.3

  The polymer-bound palladium-catalyzed cross-coupling reaction of electrophiles(i.e., halides and triflates) with organoboron compounds to form carbon-carbon bonds was achieved at mild conditions with very high activity in the Suzuki coupling reaction. The polymeric catalyst can be easily separated from a reaction mixture and reused more than 10 times with no decrease in activity

  亲电子试剂（即卤化物和三氟甲磺酸酯）与有机硼化合物形成碳-碳键的聚合物结合的钯催化的交叉偶联反应在Suzuki偶联反应中在温和条件下具有很高的活性实现。可以容易地从反应混合物中分离出聚合物催化剂，并重复使用超过10次，而不会降低活性
• Stereo- and Regiospecific Synthesis of Trisubstituted Alkenes via the Palladium-catalyzed Cross-coupling Reaction of Diisopropyl (<i>E</i>)-(1-Alkyl-1-alkenyl)boronates with Organic Halides
  作者：Makoto Satoh、Norio Miyaura、Akira Suzuki

  DOI：10.1246/cl.1986.1329

  日期：1986.8.5

  The reaction of diisopropyl (Z)-(1-bromo-1-alkenyl)boronates readily obtainable, with organolithiums and bases takes place readily to give (E)-(1-organo-1-alkenyl)boronates, the cross-coupling of which with various organic halides proceeds smoothly in the presence of Pd-catalyst and base to afford stereodefined trisubstituted alkenes in good yields.

  容易获得的二异丙基 (Z)-(1-溴-1-烯基) 硼酸酯与有机锂和碱的反应很容易得到 (E)-(1-有机-1-烯基) 硼酸酯，它与各种有机卤化物在钯催化剂和碱的存在下顺利进行，以良好的收率提供立体定义的三取代烯烃。
• Palladium-catalyzed cross-coupling reaction of organoboron compounds with organic triflates
  作者：Takayuki Ohe、Norio Miyaura、Akira Suzuki

  DOI：10.1021/jo00060a041

  日期：1993.4

  The cross-coupling reaction of 9-alkyl-9-borabicyclo[3.3.1]nonane (9-R-9-BBN), 1-alkenyl-1,3,2-benzodioxaborole, or aryl boronic acid with 1-alkenyl or aryl triflates in the presence of K3PO4 (1.5 equiv) and a catalytic amount of Pd(PPh3)4 or Cl2Pd(dppf) resulted in high yields. The reaction conditions are sufficiently mild so that a variety of functionalized alkenes, alkadienes, and arenes are readily obtained. The utility of the present reaction was demonstrated by the cyclization of omega-alkenyl triflates leading to a benzo-fused cycloalkene and bicyclic alkene via a hydroboration-intramolecular coupling sequence.
• Molybdenum metalloazines. New reagents for carbon-carbon double bond formation by an organometallic analog of the Wittig reaction
  作者：John A. Smegal、Ingrid K. Meier、Jeffrey. Schwartz

  DOI：10.1021/ja00266a047

  日期：1986.3