(E)-2-methyl-1,4-hexadien-3-ol | 52755-41-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-2-methyl-1,4-hexadien-3-ol
• 英文别名: 2-methyl-hexa-1,4t-dien-3-ol；(4E)-2-methylhexa-1,4-dien-3-ol
• CAS: 52755-41-6
• 化学式: C₇H₁₂O
• 分子量: 112.172
• InChiKey: NXQIZWACLZRURH-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  (E)-2-methyl-1,4-hexadien-3-ol 在 copper(l) iodide 作用下， 以 乙醚 为溶剂， 生成 (E,Z)-5-methyl-2,5-decadien
  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
• 作为产物：
  描述：

  2-methylhexa-1,5-dien-3-one 在 aluminum isopropoxide 、 异丙醇 作用下， 生成 (E)-2-methyl-1,4-hexadien-3-ol
  参考文献：
  名称：

  Nasarow; Kachniaschwili, Sb. Statei Obshch. Khim., 1953, p. 905,910

  摘要：

  DOI：

文献信息

• Synthesis, Structure, and Reactivity of Alkyl-Substituted Half-Sandwich η⁵-Pentadienyl Complexes of Cobalt
  作者：Kai E. O. Ylijoki、Ross D. Witherell、Andrew D. Kirk、Sebastian Böcklein、Verner A. Lofstrand、Robert McDonald、Michael J. Ferguson、Jeffrey M. Stryker

  DOI：10.1021/om900754h

  日期：2009.12.14

  Alkyl-substituted η5-pentadienyl complexes of cobalt have been reported to undergo [5 + 2] cycloaddition reactions with alkynes to form substituted η2,η3- and η5-cycloheptadienyl products, providing a new route to the synthesis of substituted cycloheptadienes. A series of cyclopentadienyl and pentamethylcyclopentadienyl cobalt(III) η5-pentadienyl complexes have been prepared, incorporating alkyl and

  烷基取代的η 5钴-戊二烯基络合物已经报道接受[5 + 2]环加成与炔烃形成η取代的反应2，η 3 -和η 5个-cycloheptadienyl产品，提供了新的途径取代的环庚二烯的合成。一系列环戊二烯基五甲基环戊二烯和钴（III）η 5已经制备了-戊二烯基配合物，在戊二烯基配体的各个位置上引入了烷基和芳基取代基。晶体配合物已经在光谱学上以及在固态下通过X射线晶体学被完全表征。烷基取代的戊二烯基配合物可以通过一系列方法来制备，最通常通过酸促进脱水原位衍生η 2 -或η 4 -dienol络合物。从共轭（1,3-）或非共轭（1,4-）二烯基醇开始，已开发出这种经典策略的两个变体。对于这两种环戊二烯基五甲基环戊二烯和辅助配体，取代的η 5-戊二烯基络合物以合理至良好的分离产率获得，受限于起始烯丙基醇的取代程度。阳离子钴（III）η 5 -戊二烯基络合物是无限稳定对空气和湿气; 分离和纯化通过在
• Regioselectivity in the claisen rearrangement of -allylic alcohols: Electronic and steric effects of C-4 substituents
  作者：Kathlyn A. Parker、James G. Farmar

  DOI：10.1016/s0040-4039(00)89215-1

  日期：1985.1

  Enol ethers of 1,4-dien-3-ols in which one allylic double bond is substituted with a methoxyl or alkyl group at C-4 undergo Claisen rearrangement in which the unsubstituted olefin participates preferentially. Rearrangement to the substituted olefin has been shown to be retarded by both electronic and steric effects.

  其中一个烯丙基双键在C-4处被甲氧基或烷基取代的1,4-二烯-3-醇的烯醇醚发生克莱森重排，未取代的烯烃优先参与其中。已显示出电子和空间位阻都阻碍了对取代烯烃的重排。
• Martin, Annales de Chimie (Cachan, France), 1959, vol. <13>1, p. 541,561
  作者：Martin

  DOI：——

  日期：——
• 648. Alkenylation with lithium alkenyls. Part XIII. 1-Methylvinyl-lithium (isoPropenyl-lithium)
  作者：E. A. Braude、E. A. Evans

  DOI：10.1039/jr9560003333

  日期：——
• Vinyl migration in Wittig rearrangements
  作者：Valentin Rautenstrauch、George Buchi、Hans Wuest

  DOI：10.1021/ja00815a042

  日期：1974.4