Hexa-1,2-dien-4-ol | 4376-43-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Hexa-1,2-dien-4-ol
• 英文别名: Hexadien-(1,2)-ol-(4)
• CAS: 4376-43-6
• 化学式: C₆H₁₀O
• 分子量: 98.1448
• InChiKey: YGPFRDUYARNNCE-UHFFFAOYSA-N

物化性质

• 沸点：
  138.9±8.0 °C(Predicted)
• 密度：
  0.823±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  Hexa-1,2-dien-4-ol 在 吡啶 、 4-二甲氨基吡啶 、 palladium diacetate 、 lithium bromide 作用下， 以 溶剂黄146 为溶剂， 反应 6.0h， 生成 5-bromo-3-ethyl-4-cyclohexene-1,1,2,2-tetracarbonitrile
  参考文献：
  名称：

  Palladium(II)-Catalyzed S_N2‘ Reactions of α-Allenic Acetates. Stereoconvergent Synthesis of (Z,E)-2-Bromo-1,3-dienes

  摘要：

  The reaction of acetylated a-allenic alcohols with LiBr in the presence of 1.5 mol % of Pd(OAc)(2) provides easy access to substituted (Z,E)-2-bromo-1,3-dienes in good yields with excellent diastereoselectivity. Both secondary and tertiary acetates as well as terminal and nonterminal allenes were studied to investigate the scope and the limitations of the reaction. A mechanism is proposed to clarify how a diastereomeric mixture of the starting compound is transformed into a single diastereomer of the product.

  DOI：

  10.1021/jo015950x
• 作为产物：
  描述：

  在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 Hexa-1,2-dien-4-ol
  参考文献：
  名称：

  Highly efficient synthesis of alka-1,3-dien-2-yltitanium compounds from alka-2,3-dienyl carbonates. A new, practical synthesis of 1,3-dienes and 2-iodo-1,3-dienes

  摘要：

  Treatment of carbonates of alka-2,3-dien-1-ols 2 with (eta(2)-propene)Ti(O-i-Pr)(2) (I) resulted in oxidative addition to afford 1,3-dien-2-yltitanium compounds 3, which react readily with electrophiles such as H+, I-2 and aldehydes. The reaction with H+ and I-2 proceeds highly regioselectively, thus providing an efficient and practical method for synthesis of 1,3-dienes and 2-iodo-1,3-dienes. Copyright (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(96)02126-0
• 作为试剂：
  描述：

  在 1,4-双(二苯基膦)丁烷 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ Hexa-1,2-dien-4-ol 、 四丁基氯化铵 、 potassium acetate 作用下， 以82%的产率得到
  参考文献：
  名称：

  Investigations of Pd-Catalyzed Aryl Substitution Reactions. A Case Study towards Zoanthenol

  摘要：

  DOI：

  10.3987/com-06-s(w)19

文献信息

• Silver(I)-Catalyzed Aminocyclization of 2,3-Butadienyl and 3,4-Pentadienyl Carbamates: An Efficient and Stereoselective Synthesis of 4-Vinyl-2-oxazolidinones and 4-Vinyltetrahydro-2<i>H</i>-1,3-oxazin-2-ones
  作者：Masanari Kimura、Shuji Tanaka、Yoshinao Tamaru

  DOI：10.1246/bcsj.68.1689

  日期：1995.6

  Silver(I) salts in combination with an appropriate base (mostly triethylamine) catalyzed the aminocyclization of N-substituted 2,3-butadienyl carbamates 1 (benzene, 50 °C) to provide 4-vinyl-2-oxazolidinones 2 in good yields. The stereoselectivity (trans-2/cis-2) ranged from 1.4 for C5-Me to >30 for C5-phenyl, isopropenyl, and t-butyl derivatives. 3,4-Pentadienyl tosylcarbamates 3, the one-carbon higher homologues of 1, underwent a similar cyclization to give 4-vinyltetrahydro-2H-1,3-oxazin-2-one 4 in synthetically useful yields and in higher trans selectivities than 1.

  银(I)盐与适当的碱（主要是三乙胺）催化N-取代的2,3-丁二烯基氨基甲酸酯1（苯，50°C）进行环化反应，以良好产率得到4-乙烯基-2-恶唑啉酮2。立体选择性（反式2/顺式2）从C5-甲基的1.4到C5-苯基、异丙烯基和叔丁基衍生物的>30不等。3,4-戊二烯基对甲苯磺酰氨基甲酸酯3，作为1的碳数多一的同系物，经历了类似的环化反应，以合成上有用的产率得到4-乙烯基四氢-2H-1,3-恶嗪-2-酮4，并且其反式选择性高于1。
• Gold-Catalyzed Regioselective Synthesis of 2- and 3-Alkynyl Furans
  作者：Yifan Li、Jonathan P. Brand、Jérôme Waser

  DOI：10.1002/anie.201302210

  日期：2013.6.24

  Chemical Matching: C2‐ or C3‐alkynylated furans were selectively synthesized by using gold catalysis. Direct C–H alkynylation of furans was achieved with C2 selectivity, and a domino cyclization/alkynylation process starting from allenes gave C3‐alkynylated products. The exact matching of the structure of the gold catalyst and an electrophilic hypervalent iodine reagent was essential for success.

  化学匹配：通过金催化选择性合成C2-或C3-烷基化的呋喃。呋喃的直接C–H炔基化是通过C2选择性实现的，从艾伦开始的多米诺环化/炔基化过程产生了C3-炔基化产物。金催化剂的结构与亲电子的高价碘试剂的精确匹配对于成功至关重要。
• Bertrand,M.; Le Gras,J., Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1963, vol. 257, p. 456 - 458
  作者：Bertrand,M.、Le Gras,J.

  DOI：——

  日期：——
• Ruthenium-Catalyzed Cyclocarbonylation of Allenyl Alcohols and Amines:  Selective Synthesis of Lactones and Lactams
  作者：Eiji Yoneda、Shi-Wei Zhang、Da-Yang Zhou、Kiyotaka Onitsuka、Shigetoshi Takahashi

  DOI：10.1021/jo0350615

  日期：2003.10.1

  Allenyl alcohols such as 4-hydroxybuta-1,2-dienes and 5-hydroxypenta-1,2-dienes having a variety of substituents undergo cyclocarbonylation in the presence of a ruthenium catalyst under mild conditions selectively to give five- and six-membered lactones in a high yield with 100% atom economy. 5-Aminopenta-1,2-dines are also cyclocarbonylated to give gamma-lactams. A possible carbonylation mechanism involving a ruthenium cluster intermediate is proposed on the basis of experimental results.
• Action du propargyltrimethylsilane sur les derives carbonyles en presence de fluorure de tetra-n-butylammonium: nouvelle voie d'acces aux alcools α-alleniques.
  作者：Jacques Pornet

  DOI：10.1016/0040-4039(81)80124-4

  日期：1981.1