2-methyl-6-phenyl-3-hexene-2-ol

• 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: 2-methyl-6-phenyl-3-hexene-2-ol
• 英文别名: (E)-2-methyl-6-phenylhex-3-en-2-ol
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: ZHLWCPCOLRSCPK-YRNVUSSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-methyl-6-phenyl-3-hexene-2-ol 在 间氯过氧苯甲酸 作用下， 以 乙醚 为溶剂， 反应 72.0h， 以67%的产率得到2-methyl-6-phenyl-3,4-epoxyhexane-2-ol
  参考文献：
  名称：

  Enantioselective epoxidation of tertiary allylic alcohols by chiral dihydroperoxides

  摘要：

  gem-Dihydroperoxides were successfully used for the enantioselective epoxidation of tertiary and primary allylic alcohols. Epoxides derived from tertiary alcohols were obtained in yields up to 71% with ee's up to 52%. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.032
• 作为产物：
  描述：

  甲基碘化镁 、 ethyl (2E)-5-phenylpent-2-enoate 以 乙醚 为溶剂， 反应 2.5h， 以48%的产率得到2-methyl-6-phenyl-3-hexene-2-ol
  参考文献：
  名称：

  Enantioselective epoxidation of tertiary allylic alcohols by chiral dihydroperoxides

  摘要：

  gem-Dihydroperoxides were successfully used for the enantioselective epoxidation of tertiary and primary allylic alcohols. Epoxides derived from tertiary alcohols were obtained in yields up to 71% with ee's up to 52%. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.032

文献信息

• Two Enabling Strategies for the Stereoselective Conversion of Internal Alkynes into Trisubstituted Alkenes
  作者：Nikolas Huwyler、Karin Radkowski、Stephan M. Rummelt、Alois Fürstner

  DOI：10.1002/chem.201702470

  日期：2017.9.7

  An expedient method for the C‐methylation of alkenylstannanes with formation of trisubstituted alkenes is described, which relies on the use of MeI in combination with copper thiophene‐2‐carboxylate (CuTC) as promotor and tetra‐n‐butylammonium diphenylphosphinate as an effective tin scavenger; in some cases, it proved beneficial to further supplement the mixture with catalytic amounts of Pd(PPh3)4

  描述了一种便捷的方法，用于链烯基锡烷的C-甲基化并形成三取代的烯烃，该方法依赖于将MeI与噻吩-2-羧酸铜（CuTC）结合使用作为促进剂，并将四苯基正膦酸四正丁铵铵作为有效的锡清道夫; 在某些情况下，进一步添加催化量的Pd（PPh 3）4混合物是有益的。在这些条件下，该反应牢固，高收率且与许多官能团相容，这些官能团在用于C-烷基化有机锡衍生物的更传统条件下可能不存在。对反应曲线的定性分析表明，反应性有机铜中间体的原位形成及其被MeI的截获仅快于同一烷基化剂对次膦酸酯添加剂的O-甲基化。为了保证高收率并防止发生净原型脱锡，必须优化反应方案，以使这些竞争过程适当地解偶联。新方法特别适合（E的立体选择性制备）存在于众多天然产物中的-2-甲基丁-2-烯-1-醇基序 或者，可以从α-羟基烯基硅氧烷前体开始访问此特定目标结构，该前体在被认为是Brook重排/烷基化序列的情况下，在暴露于CuI / LiO
• Asymmetric dihydroxylation of tertiary allylic alcohols
  作者：Zhi-Min Wang、K.Barry Sharpless

  DOI：10.1016/s0040-4039(00)61396-5

  日期：1993.12

  The asymmetric dihydroxylation (AD) of tertiary allylic alcohols is examined. Good to excellent ee's are obtained with trans-di- and tri-substituted tertiary allylic alcohols of different substitution patterns except for a trisubstituted case where the tertiary carbinol substituent is on the disubstituted olefinic carbon.

  检查了叔烯丙醇的不对称二羟基化（AD）。用具有不同取代方式的反式二取代和三取代的叔烯丙基醇获得良好至优异的ee，除了叔甲醇取代基在二取代的烯烃碳上的三取代的情况外。
• LAROCK, RICHARD C.;LEUNG, WAI-YEE, J. ORG. CHEM., 55,(1990) N6, C. 6244-6245
  作者：LAROCK, RICHARD C.、LEUNG, WAI-YEE

  DOI：——

  日期：——
• TAKEDA, TAKESHI;INOUE, TOMOYA;FUJIWARA, TOORU, CHEM. LETT.,(1988) N 6, 985-988
  作者：TAKEDA, TAKESHI、INOUE, TOMOYA、FUJIWARA, TOORU

  DOI：——

  日期：——
• Enantioselective epoxidation of tertiary allylic alcohols by chiral dihydroperoxides
  作者：Alexander Bunge、Hans-Jürgen Hamann、Dennis Dietz、Jürgen Liebscher

  DOI：10.1016/j.tet.2013.01.032

  日期：2013.3

  gem-Dihydroperoxides were successfully used for the enantioselective epoxidation of tertiary and primary allylic alcohols. Epoxides derived from tertiary alcohols were obtained in yields up to 71% with ee's up to 52%. (c) 2013 Elsevier Ltd. All rights reserved.