(E)-2-methyl-6-phenyl-3-hexene | 96025-23-9

• 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)-2-methyl-6-phenyl-3-hexene
• 英文别名: [(E)-5-methylhex-3-enyl]benzene
• CAS: 96025-23-9
• 化学式: C₁₃H₁₈
• 分子量: 174.286
• InChiKey: LFTFTZLRJZVVBF-SOFGYWHQSA-N

物化性质

• 沸点：
  236.4±10.0 °C(Predicted)
• 密度：
  0.876±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 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：

  (E)-2-methyl-6-phenyl-3-hexene 在 tetrafluoroboric acid 、 bis(pyridine)iodonium tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 生成 (5-Fluoro-3-iodo-5-methyl-hexyl)-benzene
  参考文献：
  名称：

  Stereoselective synthesis of tetralins using cationic cyclisations

  摘要：

  Tetralins, including the terpene calamenene, were prepared by 6-endo cationic cyclisations, effected by addition of an l(l) reagent to alkenylarenes, followed by reductive deiodination. An activating group on the arene was required for efficient cationic cyclisation. Good diastereoselectivity, relative to a chiral centre in the chain linking the alkene to the arene, was observed, with Z-alkenes giving predominantly 1,4-cis disubstituted tetralins, and E-alkenes giving predominantly 1,4-trans derivatives. Analogous 6-exo cationic cyclisations proved very limited in scope. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.08.033
• 作为产物：
  描述：

  5-(2-甲基丙烷-1-磺酰基)-1-苯基-1H-四唑 、 苯丙醛 在 18-冠醚-6 、 双(三甲基硅烷基)氨基钾 作用下， 以 甲苯 为溶剂， 反应 0.51h， 以87%的产率得到(E)-2-methyl-6-phenyl-3-hexene
  参考文献：
  名称：

  Simple protocol for enhanced (E)-selectivity in Julia–Kocienski reaction

  摘要：

  A short and efficient Julia-Kocienski olefination protocol, based upon the use of chelating agents (18-crown-6 or TDA-1 for K(+); 12-crown-4 or HMPA for Li(+)), was developed. This protocol enhances the (E)selectivity of the reaction and the desired olefins are obtained generally with >10:1 (E/Z)-selectivity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.02.086

文献信息

• Superbase-promoted rearrangement of oxiranes to cyclopropanes
  作者：Alessandro Mordini、Daniela Peruzzi、Francesco Russo、Michela Valacchi、Gianna Reginato、Alberto Brandi

  DOI：10.1016/j.tet.2005.01.102

  日期：2005.3

  Aryl- and alkenyl substituted oxiranes, when submitted to treatment with superbasic reagents, undergo a highly regio- and stereoselective rearrangement leading to cyclopropylmethanol derivatives. The process can also be applied to mono- and dihydroxy substituted substrates thus leading to polyhydroxylated cyclopropanes.

  芳基和烯基取代的环氧乙烷，当用超碱性试剂处理时，会发生高度的区域和立体选择性重排，从而生成环丙基甲醇衍生物。该方法也可以应用于单和二羟基取代的底物，从而产生多羟基化的环丙烷。
• Remote Arylative Substitution of Alkenes Possessing an Acetoxy Group via β‐Acetoxy Elimination
  作者：Kazuma Muto、Takaaki Kumagai、Fumitoshi Kakiuchi、Takuya Kochi

  DOI：10.1002/anie.202111396

  日期：2021.11.8

  Palladium-catalyzed remote arylative substitution was achieved for the reaction of arylboronic acids with alkenes possessing a distant acetoxy group via nondissociative chain walking and β-acetoxy elimination.

  芳基硼酸与具有远距离乙酰氧基的烯烃通过非离解链行走和β-乙酰氧基消除反应，实现了钯催化的远程芳基化取代。
• Molybdenum-Catalyzed Stereospecific Deoxygenation of Epoxides to Alkenes
  作者：Sobi Asako、Takahisa Sakae、Masahito Murai、Kazuhiko Takai

  DOI：10.1002/adsc.201600840

  日期：2016.12.22

  Mild and simple catalytic systems consisting of molybdenum(VI) dichloride dioxide [MoO2Cl2] as a catalyst and a phosphine as reductant have been developed for the stereospecific deoxygenation of epoxides to alkenes. The reactions using 1,2‐bis(diphenylphosphino)ethane (dppe) and triphenylphosphine (PPh3) proceed with retention and inversion of stereochemistry, respectively. The mild reaction tolerates

  已经开发了一种温和而简单的催化体系，该体系由二氧化钼（VI）二氧化钼（MoO 2 Cl 2）作为催化剂和膦作为还原剂组成，用于环氧化物的立体定向脱氧成烯烃。使用1,2-双（二苯基膦基）乙烷（dppe）和三苯基膦（PPh 3）的反应分别进行立体化学的保留和转化。温和的反应可容忍各种官能团的存在，并以良好的收率提供立体确定的取代的烯烃。
• Cromble, Leslie; Fernando, Candida E. C., Journal of Chemical Research, Miniprint, 1998, # 7, p. 1519 - 1537
  作者：Cromble, Leslie、Fernando, Candida E. C.

  DOI：——

  日期：——
• TAMARU, Y.;HIOKI, T.;YOSHIDA, Z., TETRAHEDERON LETT., 1984, 25, N 50, 5793-5796
  作者：TAMARU, Y.、HIOKI, T.、YOSHIDA, Z.

  DOI：——

  日期：——