(E,E)-(6-methylhepta-1,3,5-trienyl)benzene | 132430-97-8

• 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,E)-(6-methylhepta-1,3,5-trienyl)benzene
• 英文别名: [(1E,3E)-6-methylhepta-1,3,5-trienyl]benzene
• CAS: 132430-97-8
• 化学式: C₁₄H₁₆
• 分子量: 184.281
• InChiKey: QURBCJRDBHXGOK-YBRHCDHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  (3-methylbut-2-en-1-yl)diphenylphosphine oxide 在 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.58h， 生成 (E,E)-(6-methylhepta-1,3,5-trienyl)benzene
  参考文献：
  名称：

  Baudin, J. B.; Hareau, G.; Julia, S. A., Bulletin de la Societe Chimique de France, 1993, vol. 130, p. 856 - 878

  摘要：

  DOI：

文献信息

• Stereoselective synthesis of substituted 1,3,5-hexatrienes from diallylic sulfones
  作者：Xiao-Ping Cao、Tze-Lock Chan、Hak-Fun Chow、Jingren Tu

  DOI：10.1039/c39950001297

  日期：——

  Substituted 1,3,5-hexatrienes 7 can be prepared in excellent yields and with good stereoselectivity from diallylic sulfones 6 employing a modified Ramberg–Bäcklund reaction.

  利用改良的 Ramberg-Bäcklund 反应，可以从二烯丙基砜 6 中制备取代的 1,3,5-己三烯 7，产量极高，且具有良好的立体选择性。
• Use of Samarium Diiodide as an Alternative to Sodium/Mercury Amalgam in the Julia-Lythgoe Olefination
  作者：Gary E. Keck、Kenneth A. Savin、Michael A. Weglarz

  DOI：10.1021/jo00115a041

  日期：1995.5

  Studies into the use of samarium diiodide (SmI2) in the reductive elimination of 1,2-acetoxy sulfones and the reductive cleavage of vinyl sulfones are reported. Parallel investigations with sodium/mercury amalgam (Na/Hg) revealed over-reduction in several cases in which the desired products were heavily conjugated or conjugated to an aromatic moiety. A mechanistic study revealed some of the intricacies of the SmI2-promoted Julia-Lythgoe olefination. The classical Na/Hg reductive method was also examined, and an alternative mechanism is proposed. Observations described herein provide important insights into the mechanism and synthetic utility of these methods. The optimum protocol developed utilizes SmI2 reduction of vinyl sulfones in the presence of DMPU and MeOH and gives generally high yields with good to excellent E stereoselectivity.
• Trans-Selective Olefination of Carbonyl Compounds by Low-Valent Titanium-Mediated Dehydroxybenzotriazolylation
  作者：Alan R. Katritzky、Dai Cheng、Scott A. Henderson、Jianqing Li

  DOI：10.1021/jo980616v

  日期：1998.9.1

  Lithiation with n-butyllithium of a variety of benzotriazole derivatives 1a-f and 5a-d, all containing a proton alpha to the benzotriazolyl moiety, gave anions which underwent addition to aliphatic, aromatic, and alpha,beta-unsaturated aldehydes and cyclic and acyclic ketones. The resultant N-(beta-hydroxyalkyl)benzotriazole derivatives 3a-m, 6a-g, 9a-d, and 10a were dehydroxybenzotriazolylated when treated with low-valent titanium to give alkenes 4a-m, dienes 7a-j, and triene 11a, with selectivity for the trans isomers without separation of diastereoisomeric intermediates. This method offers an alternative to the three most frequently used methods for the formation of alkenes from carbonyl compounds-the Wittig, Peterson, and Julia reactions-especially in the formation of tri- and tetrasubstituted alkenes.
• An improved variant of the julia olefin synthesis: reductive elimination of β-hydroxy imidazolyl sulfones by samarium dhodide
  作者：Andrew S. Kende、José S. Mendoza

  DOI：10.1016/s0040-4039(00)97252-6

  日期：——
• KENDE, ANDREW S.;MENDOZA, JOSE S., TETRAHEDRON LETT., 31,(1990) N9, C. 7105-7108
  作者：KENDE, ANDREW S.、MENDOZA, JOSE S.

  DOI：——

  日期：——