(Z)-((hex-2-en-1-yloxy)methyl)benzene | 146330-82-7

• 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)-((hex-2-en-1-yloxy)methyl)benzene
• 英文别名: (Z)-[(hex-2-en-1-yloxy)methyl]benzene；cis-1-(benzyloxy)-2-hexene；(Z)-1-benzyloxy-2-hexene；[(Z)-hex-2-enoxy]methylbenzene
• CAS: 146330-82-7
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: AZFAFWIJYLJVFY-YWEYNIOJSA-N

物化性质

• 沸点：
  261.6±9.0 °C(Predicted)
• 密度：
  0.929±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-((hex-2-en-1-yloxy)methyl)benzene 在 sodium azide 、 magnesium(II) perchlorate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 64.0h， 生成 (2R,3R)-2-azido-1-phenylmethoxyhexan-3-ol
  参考文献：
  名称：

  Regiochemical control of the ring opening of 1,2-epoxides by means of chelating processes. 5. Synthesis and reactions of some 2,3-epoxy-1-alkanol derivatives

  摘要：

  In order to study the effect of a remote polar functionality on the regiochemistry of the ring opening of aliphatic epoxides, the synthesis and some nucleophilic additions (methanolysis, azidolysis, and aminolysis) of suitable 2,3-epoxy-1-alkanol derivatives (epoxides trans-1a-d and cis-2) were carried out. The C-3 selectivity commonly observed when nonchelating ring opening conditions are used is lower than when the epoxides are allowed to react in the presence of metal ions (Li+, Mg2+, Zn2+) due to the probable intervention of bidentate-chelated intermediates in the latter case, and in some instances an almost complete C-3 regioselection is obtained. Under identical conditions involving chelation control, trans epoxide la shows higher C-3 selectivity than cis isomer 2. A free hydroxyl functionality is not necessary in order to observe chelation-controlled regioselectivity in the epoxides that we examined.

  DOI：

  10.1021/jo00057a040
• 作为产物：
  描述：

  顺-4-苄氧基-2-丁烯-1-醇 在 甲基磺酰氯 、 lithium chloride 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 (Z)-((hex-2-en-1-yloxy)methyl)benzene
  参考文献：
  名称：

  Yadav, J. S.; Reddy, P. Satyanarayana, Synthetic Communications, 1986, vol. 16, # 9, p. 1119 - 1132

  摘要：

  DOI：

文献信息

• Supported gold nanoparticles catalyzed cis-selective semihydrogenation of alkynes using ammonium formate as the reductant
  作者：Shengzong Liang、Gerald B. Hammond、Bo Xu

  DOI：10.1039/c6cc01318j

  日期：——

  nanoparticles with low loading (0.5 mol %) are able to semihydrogenate non-fluorinated and gem-difluorinated alkynes to cis-alkenes with high selectivity, using cost-effective and easy-to-handle ammonium formate as...

  TiO2负载的金纳米粒子具有较低的负载量（0.5 mol％），能够使用经济高效且易于处理的甲酸铵作为原料，以高选择性将非氟化和宝石二氟化炔烃半氢化为顺式烯烃。
• PROCESS FOR THE SYNTHESIS OF KETONES FROM INTERNAL ALKENES
  申请人：CALIFORNIA INSTITUTE OF TECHNOLOGY

  公开号：US20140194604A1

  公开（公告）日：2014-07-10

  The present invention is directed to methods for oxidizing internal olefins to ketones. In various embodiments, each method comprising contacting an organic substrate, having an initial internal olefin, with a mixture of (a) a biscationic palladium salt; and (b) an oxidizing agent; dissolved or dispersed in a solvent system to form a reaction mixture, said solvent system comprising at least one C 2-6 carbon nitrile and optionally at least one secondary alkyl amide, said method conducted under conditions sufficient to convert at least 50 mol % of the initial internal olefin to a ketone, said ketone positioned on a carbon of the initial internal olefin. The transformation occurs at room temperature and shows wide substrate scope. Applications to the oxidation of seed oil derivatives and a bioactive natural product are described.

  本发明涉及将内烯烃氧化为酮的方法。在各种实施方式中，每种方法包括将具有初始内烯烃的有机底物与（a）双阳离子钯盐的混合物；和（b）氧化剂接触，溶解或分散在溶剂体系中形成反应混合物，所述溶剂体系包括至少一种C2-6碳腈和可选地至少一种次烷基酰胺，所述方法在足以将初始内烯烃的至少50摩尔％转化为酮的条件下进行，所述酮位于初始内烯烃的碳上。该转化在室温下发生，并显示出广泛的底物范围。描述了将其应用于种子油衍生物和生物活性天然产物的氧化。
• Diastereoselective Borocyclopropanation of Allylic Ethers Using a Boromethylzinc Carbenoid
  作者：Guillaume Benoit、André B. Charette

  DOI：10.1021/jacs.6b09090

  日期：2017.2.1

  borocyclopropanation of (E)- and (Z)-allylic ethers and styrene derivatives via the Simmons-Smith reaction using a novel boromethylzinc carbenoid is described. The carbenoid precursor is prepared via a 3-step sequence from inexpensive and commercially available starting materials. This methodology allows for the preparation of 1,2,3-substituted borocyclopropanes in high yields and diastereoselectivities

  描述了 (E)-和 (Z)-烯丙基醚和苯乙烯衍生物通过 Simmons-Smith 反应使用新型硼甲基锌卡宾进行硼环丙烷化。卡宾前体是通过 3 步序列从廉价且市售的起始材料制备的。这种方法允许以高产率和非对映选择性制备 1,2,3-取代的硼环丙烷。还进行了几个后功能化反应来说明这些构建块的多功能性。
• First Evidence for the Formation of a Geminal Dizinc Carbenoid:  A Highly Stereoselective Synthesis of 1,2,3-Substituted Cyclopropanes
  作者：André B. Charette、Alexandre Gagnon、Jean-François Fournier

  DOI：10.1021/ja017230d

  日期：2002.1.1

  Significant amounts of novel gem-dizinc carbenoids (RZnCHIZnR) are formed when diethylzinc is mixed with iodoform in CH2Cl2 at 0 degrees C. This reagent was shown to be effective in the cyclopropanation of butenediol derivatives to generate a cyclopropylzinc intermediate that could be trapped with a variety of electrophiles. 1,2,3-Substituted cyclopropane derivatives are formed with excellent diastereoselectivities

  当二乙基锌与碘仿在 0 摄氏度的 CH2Cl2 中混合时，会形成大量的新型 gem-dizinc carbenoids (RZnCHIZnR)。该试剂被证明在丁烯二醇衍生物的环丙烷化中有效，生成环丙基锌中间体，该中间体可以用各种亲电试剂。1,2,3-取代的环丙烷衍生物通过使用这种简单的方法形成，具有优异的非对映选择性。
• <i>Z</i>-Selective alkyne semi-hydrogenation catalysed by piano-stool <i>N</i>-heterocyclic carbene iron complexes
  作者：Chloe Johnson、Martin Albrecht

  DOI：10.1039/c8cy00681d

  日期：——

  NHC iron(II) piano-stool complexes catalyse the selective semi-hydrogenation of alkynes to alkenes using silanes as reducing agents. Aromatic terminal alkynes are converted to styrenes without over-reduction to ethylbenzene derivatives. Furthermore, internal aryl alkynes afford cis-alkenes with excellent Z-selectivity.

  NHC铁（II）钢琴凳配合物使用硅烷作为还原剂，催化炔烃选择性地半氢化为烯烃。芳族末端炔烃可转化为苯乙烯，而不会过度还原为乙苯衍生物。此外，内部芳基炔烃可提供具有出色Z选择性的顺式烯烃。