(2E,4E)-2,4-decadiene | 62947-49-3

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: (2E,4E)-2,4-decadiene
• 英文别名: (E,E)-2,4-decadiene；deca-2,4-diene；deca-2t,4t-diene；2,4-decadiene；(E,E)-Deca-2,4-dien；trans-2,trans-4-Decadiene；(2E,4E)-deca-2,4-diene
• CAS: 62947-49-3
• 化学式: C₁₀H₁₈
• 分子量: 138.253
• InChiKey: RMWHYWJWLBDARH-WJDMQLPWSA-N

物化性质

• 沸点：
  178.1±7.0 °C(Predicted)
• 密度：
  0.764±0.06 g/cm3(Predicted)
• 保留指数：
  1040.5

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  (E)-hexa-1,4-dien-3-ol 在 copper(l) iodide 作用下， 以 乙醚 为溶剂， 生成 (2E,4E)-2,4-decadiene
  参考文献：
  名称：

  Alkylation of allylic derivatives. 17. Cross-coupling reactions of diallylic pivalates with butyl- and phenylcopper reagents

  摘要：

  Cross coupling (Z)-1-phenyl-1,4-pentadien-3-yl pivalate (cis-1-OPiv) with LiCuBu2, LiCu(CN)Bu, LiCuPh2, and LiCu(CN)Ph gives only the fully conjugated gamma-coupling product. With LiCuBu2, substantial loss of double-bond configuration occurs to give primarily the all-trans coupling product. With other cuprates, no detectable loss of double-bond configuration was observed. Cross coupling (Z)-3-(2-phenylethenyl)2-cyclohexen-1-yl pivalate (cis-18-OPiv) with LiCuBu2, LiCuPh2, and LiCu(CN) ph gives only alpha-coupling product; with LiCu(CN)Bu, a mixture of alpha, gamma, and epsilon coupling product was obtained. Cross coupling with LiCuBu2, results in loss of double-bond configuration in the alpha-alkylation product. With the other cuprates, no loss of double-bond configuration was detected in the alpha and gamma coupling product. These results have profound mechanistic implications, which are discussed. The relationship between structure and reactivity was also investigated. A variety of diallylic pivalates (1-5 OPiv) were prepared and cross coupled with LiCuBu2, LiCu(CN)Bu, LiCuPh2, and LiCu(CN)Ph. Generally, coupling occurs at the least-substituted allylic system; mechanistic implications are discussed.

  DOI：

  10.1021/jo00007a055

文献信息

• Tunable stereoselective alkene synthesis by treatment of activated imines with nonstabilized phosphonium ylides
  作者：De-Jun Dong、Yuan Li、Jie-Qi Wang、Shi-Kai Tian

  DOI：10.1039/c0cc04739b

  日期：——

  A broad range of readily accessible N-sulfonyl imines undergo olefination reaction with nonstabilized phosphonium ylides under mild conditions to afford an array of both Z- and E-isomers of 1,2-disubstituted alkenes, allylic alcohols, and allylic amines in good yields and with greater than 99 : 1 stereoselectivity.

  各种容易获得的N-磺酰基亚胺在温和的条件下与不稳定的烷基化物进行烯化反应，从而以良好的收率获得了一系列1,2-二取代的烯烃，烯丙醇和烯丙基胺的Z-异构体和E-异构体。具有大于99：1的立体选择性。
• Grignard allylic substitution reaction catalyzed by 1,2,3-triazol-5-ylidene magnesium complexes
  作者：Ryosuke Nomura、Yuji Tsuchiya、Hiroyuki Ishikawa、Sentaro Okamoto

  DOI：10.1016/j.tetlet.2012.12.124

  日期：2013.3

  Allylic chlorides and phosphates reacted with alkyl-Grignard reagent in an S(N)2'-selective manner in the presence of a catalytic amount of 1,2,3-triazol-5-ylidenes to provide a-branched alkenes. (C) 2013 Elsevier Ltd. All rights reserved.
• Direct substitution of hydroxyl groups of allyl alcohols with alkyl groups by the reaction of lithium allyloxyalkylcuprates with N,N-methylphenylaminotriphenylphosphonium iodide. Regio- and stereoselective olefin synthesis
  作者：Yoshio Tanigawa、Hiroshi Kanamaru、Akio Sonoda、Shunichi Murahashi

  DOI：10.1021/ja00449a068

  日期：1977.3
• Boughdady, Nabil M.; Chynoweth, Kevin R.; Hewitt, David G., Australian Journal of Chemistry, 1991, vol. 44, # 4, p. 567 - 579
  作者：Boughdady, Nabil M.、Chynoweth, Kevin R.、Hewitt, David G.

  DOI：——

  日期：——
• UNDERINER, TED L.;GOERING, HARLAN L., J. ORG. CHEM., 56,(1991) N, C. 2563-2572
  作者：UNDERINER, TED L.、GOERING, HARLAN L.

  DOI：——

  日期：——