(6E,10Z)-2,6,11,15-tetramethylhexadeca-2,6,10,14-tetraene | 35162-81-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (6E,10Z)-2,6,11,15-tetramethylhexadeca-2,6,10,14-tetraene
• 英文别名: (6E,10Z)-2,6,11,15-tetramethyl-hexadeca-2,6,10,14-tetraene；cis,trans-Nerylgeranyl；Neryl-geranyl；cis,trans-bigeranyl；cis,trans-digeranyl；nerylgeranyl；Digeranyl；(6Z,10E)-2,6,11,15-tetramethylhexadeca-2,6,10,14-tetraene
• CAS: 35162-81-3
• 化学式: C₂₀H₃₄
• 分子量: 274.49
• InChiKey: UXUPDBJCOQWXPC-LRVMPXQBSA-N

物化性质

• 沸点：
  354.8±32.0 °C(Predicted)
• 密度：
  0.825±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  20
• 可旋转键数：
  9
• 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：

  橙花醇 在 二氯二茂钛 锰 、 四溴化碳 、 三苯基膦 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 2.25h， 生成 (6E,10Z)-2,6,11,15-tetramethylhexadeca-2,6,10,14-tetraene
  参考文献：
  名称：

  Reductive Coupling of Terpenic Allylic Halides Catalyzed by Cp₂TiCl:  A Short and Efficient Asymmetric Synthesis of Onocerane Triterpenes

  摘要：

  Titanocene chloride catalyzes the regioselective alpha,alpha '-homocoupling of terpenic allylic halides. This process has been employed in the short and effective synthesis of terpenoids such as beta-onoceradiene (1), beta-onocerin (2), and squalene (3). Evidence is presented for eta(1)-allyltitanium species being involved in the coupling.

  DOI：

  10.1021/ol050335r

文献信息

• Ti/Pd Bimetallic Systems for the Efficient Allylation of Carbonyl Compounds and Homocoupling Reactions
  作者：Alba Millán、Araceli G. Campaña、Btissam Bazdi、Delia Miguel、Luis Álvarez de Cienfuegos、Antonio M. Echavarren、Juan M. Cuerva

  DOI：10.1002/chem.201003315

  日期：2011.3.28

  The allylation, crotylation and prenylation of aldehydes and ketones with stable and easily handled allylic carbonates is promoted by a Ti/Pd catalytic system. This Ti/Pd bimetallic system is especially convenient for the allylation of ketones, which are infrequent substrates in other related protocols, and can be carried out intramolecularly to yield five‐ and six‐membered cyclic products with good

  Ti / Pd催化体系可促进醛和酮与稳定且易于处理的烯丙基碳酸酯的烯丙基化，丁酰化和烯丙基化。这种Ti / Pd双金属体系特别适合于酮的烯丙基化，酮是其他相关规程中不常见的底物，并且可以在分子内进行生产，从而产生具有良好立体选择性的五元和六元环状产物。此外，Ti / Pd介导的还原反应和Würtz型二聚反应可以很容易地从碳酸烯丙酯和羧酸酯中进行。
• PALLADIUM-CATALYZED COUPLING OF ALLYLIC ACETATES WITH ZINC
  作者：Shin-ichi Sasaoka、Taku Yamamoto、Hideki Kinoshita、Katsuhiko Inomata、Hiroshi Kotake

  DOI：10.1246/cl.1985.315

  日期：1985.3.5

  Allylic acetates were coupled with zinc dust in the presence of a catalytic amount of [Pd(PPh3)4] to give the corresponding 1,5-dienes under mild conditions in high yields. Significant co-solvent effects were found with methanol or 1,2-ethanediol in tetrahydrofuran.

  在催化量的 [Pd(PPh3)4] 存在下，乙酸烯丙酯与锌粉偶联，在温和条件下以高产率得到相应的 1,5-二烯。发现四氢呋喃中的甲醇或 1,2-乙二醇具有显着的共溶剂效应。
• Hexacarbonylmolybdenum(0)-Catalyzed Reductive Coupling of Allylic Acetates
  作者：Yoshiro Masuyama、Kiyotaka Otake、Yasuhiko Kurusu

  DOI：10.1246/bcsj.60.1527

  日期：1987.4

  The reaction of allylic acetates with zinc in the presence of a catalytic amount of hexacarbonylmolybdenum(0) led to reductive coupling for the formation of a 1,5-diene framework. Reductive coupling of nerolidyl acetate provided squalene and its isomers in high yield.

  在一定量的六羰基钼（0）催化下，烯丙基乙酸酯与锌发生反应，产生还原偶联，形成 1,5 二烯框架。乙酸橙烷基酯的还原偶联反应可提供高产率的角鲨烯及其异构体。
• PALLADIUM-CATALYZED REGIO- AND STEREOSELECTIVE DESULFONYLATION OF ALLYLIC SULFONES WITH LiHBEt₃. APPLICATION TO THE SYNTHESIS OF SQUALENE
  作者：Mitsunobu Mohri、Hideki Kinoshita、Katsuhiko Inomata、Hiroshi Kotake

  DOI：10.1246/cl.1985.451

  日期：1985.4.5

  Allylic p-tolyl sulfones were easily desulfonylated to the corresponding alkenes by LiHBEt3 in the presence of a catalytic amount of [PdCl2(dppp)] under mild conditions with the preservation of the original stereochemistry. This reaction was successfully applied to the synthesis of squalene.

  LiHBEt3 在一定量的 [PdCl2(dppp)]催化下，能在温和的条件下轻松地将烯丙基对甲苯砜脱磺化为相应的烯烃，并保持原有的立体化学结构。该反应被成功应用于合成角鲨烯。
• Highly selective homocoupling reaction of allylic halides using barium metal
  作者：Akira Yanagisawa、Hiroaki Hibino、Shigeki Habaue、Yoshiyuki Hisada、Hisashi Yamamoto

  DOI：10.1021/jo00050a006

  日期：1992.11

  The highly alpha,alpha' selective and stereocontrolled homocoupling reaction of allylic halides was achieved using barium reagent. The double-bond geometry of the starting allylic chloride was completely retained. alpha,alpha' Cross-coupling products were also prepared stereospecifically and regioselectively by this method.