(1E,4E)-nona-1,4-diene-1-ylbenzene | 73062-33-6

• 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: (1E,4E)-nona-1,4-diene-1-ylbenzene
• 英文别名: (E,E)-1-phenyl-1,3-nonadiene；(E,E)-1-phenyl-1,4-nonadiene；[(1E,4E)-nona-1,4-dienyl]benzene
• CAS: 73062-33-6
• 化学式: C₁₅H₂₀
• 分子量: 200.324
• InChiKey: XJOXOIDJZBQWMF-HFACTSAFSA-N

物化性质

• 沸点：
  72-73 °C(Press: 20 Torr)
• 密度：
  0.898±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  1-三甲基硅烷-1-己炔 在 二氯二茂钛 、 ISOBUTYLMAGNESIUM BROMIDE 、 氢碘酸 作用下， 以 乙醚 、 苯 为溶剂， 反应 8.0h， 生成 (1E,4E)-nona-1,4-diene-1-ylbenzene
  参考文献：
  名称：

  Zhao, Hong; Hao, Wenyan; Cai, Mingzhong, Journal of Chemical Research - Part S, 2003, # 12, p. 780 - 781

  摘要：

  DOI：

文献信息

• Oxime Palladacycle-Catalyzed Suzuki-Miyaura Alkenylation of Aryl, Heteroaryl, Benzyl, and Allyl Chlorides under Microwave Irradiation Conditions
  作者：José F. Cívicos、Diego A. Alonso、Carmen Nájera

  DOI：10.1002/adsc.201100019

  日期：2011.7

  cocatalyst, and potassium carbonate as base in N,N‐dimethylformamide at 130 °C under microwave irradiation conditions. Under these conditions, styrenes, stilbenes, and alkenylarenes are obtained in good to high yields, and with high regio‐ and diastereoselectivities in only 20 min. The reported protocol is also very efficient for the regioselective alkenylation of benzyl and allyl chlorides to afford allylarenes

  提出了一种在微波辐射下钯催化的有机氯化物的Suzuki-Miyaura交叉偶联的简单新方案。使用4,4'-二氯二苯甲酮肟肟衍生的Palladacycle 1b作为预催化剂，在0.1至0.5 mol％的钯载量下，三（叔丁基）phosph四氟硼酸[[ HP（t- Bu）3 ] BF 4 }作为配体，四正丁基氢氧化铵作为助催化剂，碳酸钾作为碱在N，N中在微波辐射条件下于130°C时生成二甲基甲酰胺。在这些条件下，仅需20分钟即可获得高至高收率的苯乙烯，对苯二甲酸酯和烯基芳烃，并且具有很高的区域选择性和非对映选择性。报告的方案对于苄基和烯丙基氯的区域选择性烯基化反应也非常有效，可提供烯丙基芳烃和1,4-二烯。
• Nickel-Catalyzed Ligand-Controlled Regioselective Allylic Alkenylation of Allylic Alcohols with Easily Accessible Alkenyl Boronates: Synthesis of 1,4-Dienes
  作者：Xuye Wu、Mei Yang、Yuanhong Liu

  DOI：10.1021/acs.orglett.3c03219

  日期：2023.12.15

  nickel-catalyzed direct reaction of allylic alcohols with easily accessible alkenyl boronates has been developed, which provides valuable 1,4-dienes with high regio- and stereoselectivity in good to excellent yields, wide substrate scope, and functional group compatibility. The catalytic system simply consists of Ni(cod)2 as the catalyst and a ligand, without a need for a base and alcohol activator in most

  镍催化的烯丙醇与易于获得的烯基硼酸酯的直接反应已被开发出来，该反应可提供有价值的 1,4-二烯，具有高区域选择性和立体选择性，产率良好至优异，底物范围宽，且官能团相容性好。该催化体系仅由作为催化剂的Ni(cod) 2和配体组成，大多数情况下不需要碱和醇活化剂。辅助配体的正确选择对于该反应非常重要。根据烯丙醇和/或烯基硼酸酯的取代模式，使用不同的配体来提高反应效率。
• Alkylation of allylic derivatives. 17. Cross-coupling reactions of diallylic pivalates with butyl- and phenylcopper reagents
  作者：Ted L. Underiner、Harlan L. Goering

  DOI：10.1021/jo00007a055

  日期：1991.3

  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.
• New procedure for synthesis of 1,4-dienes and monoolefins via methylcopper-induced cross-coupling of alkenylboranes with organic halides
  作者：Hidetaka Yatagai

  DOI：10.1021/jo01297a021

  日期：1980.4
• YATAGAI HIDETAKA, J. ORG. CHEM. 1980, 45, NO 9, 1640-1644
  作者：YATAGAI HIDETAKA

  DOI：——

  日期：——