(E)-((hex-2-en-1-yloxy)methyl)benzene | 146330-81-6

• 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: (E)-((hex-2-en-1-yloxy)methyl)benzene
• 英文别名: (E)-((hex-2-enyloxy)methyl)benzene；trans-1-(benzyloxy)-2-hexene；trans-2-hexenyl benzyl ether；(E)-1-(benzyloxy)-2-hexene；(E)-1-benzyloxy-2-hexene；[(E)-hex-2-enoxy]methylbenzene
• CAS: 146330-81-6
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: AZFAFWIJYLJVFY-XBXARRHUSA-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：

  (E)-((hex-2-en-1-yloxy)methyl)benzene 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以91%的产率得到噁丙环,2-[(苯基甲氧基)甲基]-3-丙基-,(2R,3S)-rel-
  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：

  反式-2-己烯酸乙酯 在 sodium hydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 (E)-((hex-2-en-1-yloxy)methyl)benzene
  参考文献：
  名称：

  无环烯丙基醚与有机锂试剂的不对称烯丙基烷基化

  摘要：

  报道了用有机锂试剂对烯丙基醚进行的高效，区域和对映选择性的Cu I /亚磷酰胺催化的不对称烯丙基烷基化反应（参见方案）。由于与不同的路易斯酸具有相容性，因此使用有机锂试剂对于这种催化的CC键形成至关重要。（S）-戊二酸的最短合成证明了烯丙基醚在铜催化的条件下与有机锂试剂的多功能性。

  DOI：

  10.1002/chem.201202251

文献信息

• Allylic Etherification via Ir(I)/Zn(II) Bimetallic Catalysis
  作者：Justin P. Roberts、Chulbom Lee

  DOI：10.1021/ol0508328

  日期：2005.6.1

  [reaction: see text] An efficient allylic etherification of aliphatic alcohols with allylic carbonates has been achieved by an iridium catalysis using stoichiometric zinc alkoxides or a two-component bimetallic catalytic system where the Ir(I) catalyst acts on allylic carbonates to generate electrophiles while aliphatic alcohols are separately activated by Zn(II) coordination to function as nucleophilies

  [反应：见正文]通过使用化学计量的醇锌或二组分双金属催化体系的铱催化，实现了脂肪族醇与碳酸烯丙酯的有效烯丙基醚化反应，其中Ir（I）催化剂作用于碳酸烯丙酯以生成亲电子试剂，而脂族醇通过Zn（II）配位分别激活，以发挥亲核作用。该反应具有完全的区域特异性，并且可以耐受各种官能团。
• Arabinose-Derived Ketones as Catalysts for Asymmetric Epoxidation of Alkenes
  作者：Tony K. M. Shing、Gulice Y. C. Leung、To Luk

  DOI：10.1021/jo050928f

  日期：2005.9.1

  Readily available arabinose-derived ketones, containing a tunable butane-2,3-diacetal as the steric blocker, displayed increasing enantioselectivity (up to 90% ee) with the size of the acetal alkyl group in catalytic asymmetric epoxidation of trans-disubstituted and trisubstituted alkenes. The stereochemical communication between our ketone catalysts and the alkene substrates is mainly due to steric

  现成的阿拉伯糖衍生的酮，包含可调节的2,3-丁烷作为空间阻滞剂，在反式-二取代和三取代的催化不对称环氧化反应中，随着乙缩醛烷基大小的增加，对映选择性增加（最多90％ee）。烯烃。我们的酮催化剂与烯烃底物之间的立体化学连通主要是由于空间效应，而涉及底物和催化剂的苯基之间的π-π相互作用的电子效应在我们的系统中似乎不起作用。
• 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。
• Iridium-Catalyzed Regio- and Enantioselective Hydroarylation of Alkenyl Ethers by Olefin Isomerization
  作者：Yusuke Ebe、Mitsuki Onoda、Takahiro Nishimura、Hideki Yorimitsu

  DOI：10.1002/anie.201702286

  日期：2017.5.8

  Iridium‐catalyzed hydroarylation of alkenyl ethers, such as allylic and homoallylic ethers, by C−H bond activation gave high yields of the corresponding addition products, where the aryl groups were selectively installed at the α‐carbon atom to the alkoxy group. The reaction involves an isomerization of the alkenyl ethers into the corresponding 1‐alkenyl ethers, which then undergo the regio‐ and enantioselective

  烯基醚（如烯丙基和均烯丙基醚）的铱催化的C-H键活化产生高产率的相应加成产物，其中芳基被选择性地安装在烷氧基的α-碳原子上。该反应涉及烯基醚异构化为相应的1-烯基醚，然后进行区域和对映选择性的氢芳基化。
• <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。