2-acetoxy-3,4-pentadiene | 17615-18-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-acetoxy-3,4-pentadiene
• 英文别名: 4-acetoxy-1,2-pentadiene；4-acetoxy-penta-1,2-diene；Pentadien-(1,2)-yl-(4)-acetat
• CAS: 17615-18-8
• 化学式: C₇H₁₀O₂
• 分子量: 126.155
• InChiKey: KMVBNCJDRLCYLZ-UHFFFAOYSA-N

物化性质

• 沸点：
  154.6±10.0 °C(Predicted)
• 密度：
  0.890±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-acetoxy-3,4-pentadiene 在 C₅H₅N 、 NaOH 作用下， 以 吡啶 、 甲醇 、 水 为溶剂， 生成 (3E)-1,3-pentadien-2-yl(4'-(N,N-dimethylamino)pyridine)bis(dimethylglyoximato)cobalt(III)
  参考文献：
  名称：

  Synthesis of Cobalt Substituted 1,3-Diene Complexes with Unusual Structures and Their Exo Selective Diels-Alder Reactions

  摘要：

  The synthesis and characterization (including crystallographic data) of several substituted-pyridine (Rpyr) cobalt bis(dimethylglyoxime) 1,3-butadiene complexes (R = H, tBu, 3,5-diMe, and N,N-dimethylamino) and their Diels-Alder reactions with a variety of dienophiles are reported here. The cobalt-carbon bonds in the Diels-Alder cycloadducts can be cleaved so that cobalt complexes as well as functionalized organic cycloadducts are recovered. Through these cobalt-carbon bond cleavage reactions, cobalt-diene complexes can serve as synthons for a variety of 1,3-dienes such as 1,3-butadiene, 2-(trimethylsiloxy)-1,3-butadiene, iodoprene, (E)-1-methoxy-3-(trimethylsiloxy)-1,3-butadiene (Danishefsky's diene), and 1,2-dichloro-1,3-butadiene. The preparation of several cobalt-substituted 1,2- and 1,3-pentadiene complexes and highly exo-selective Diels-Alder reactions of the 1,3-pentadiene complexes are then discussed followed by demetalation reactions of these more highly substituted cobalt cycloadducts. These demetalation reactions maintain the stereochemical integrity found in the metal cycloadducts and also lead to cobalt recovery.

  DOI：

  10.1021/ja00094a037
• 作为产物：
  描述：

  5-chloro-3-pentyn-2-ol 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 甲基锂 作用下， 反应 4.0h， 生成 2-acetoxy-3,4-pentadiene
  参考文献：
  名称：

  Synthesis of Cobalt Substituted 1,3-Diene Complexes with Unusual Structures and Their Exo Selective Diels-Alder Reactions

  摘要：

  The synthesis and characterization (including crystallographic data) of several substituted-pyridine (Rpyr) cobalt bis(dimethylglyoxime) 1,3-butadiene complexes (R = H, tBu, 3,5-diMe, and N,N-dimethylamino) and their Diels-Alder reactions with a variety of dienophiles are reported here. The cobalt-carbon bonds in the Diels-Alder cycloadducts can be cleaved so that cobalt complexes as well as functionalized organic cycloadducts are recovered. Through these cobalt-carbon bond cleavage reactions, cobalt-diene complexes can serve as synthons for a variety of 1,3-dienes such as 1,3-butadiene, 2-(trimethylsiloxy)-1,3-butadiene, iodoprene, (E)-1-methoxy-3-(trimethylsiloxy)-1,3-butadiene (Danishefsky's diene), and 1,2-dichloro-1,3-butadiene. The preparation of several cobalt-substituted 1,2- and 1,3-pentadiene complexes and highly exo-selective Diels-Alder reactions of the 1,3-pentadiene complexes are then discussed followed by demetalation reactions of these more highly substituted cobalt cycloadducts. These demetalation reactions maintain the stereochemical integrity found in the metal cycloadducts and also lead to cobalt recovery.

  DOI：

  10.1021/ja00094a037

文献信息

• Synthese stereoselective de dienes conjugues a partir d'alcools α-alleniques
  作者：Dariouche Djahanbini、Bernard Cazes、Jacques Gore

  DOI：10.1016/s0040-4020(01)88795-0

  日期：1984.1
• Perriot,P.; Gaudemar,M., Bulletin de la Societe Chimique de France, 1974, p. 2603 - 2606
  作者：Perriot,P.、Gaudemar,M.

  DOI：——

  日期：——
• Stokes, Heather L.; Matthew Richardson; Wright, Marcus W., Organometallics, 1995, vol. 14, # 12, p. 5520 - 5532
  作者：Stokes, Heather L.、Matthew Richardson、Wright, Marcus W.、Vaughn, Stacia M.、Welker, Mark E.、Liable-Sands, Louise、Rheingold, Arnold L.

  DOI：——

  日期：——
• Transition Metal Mediated <i>Exo </i>Selective Diels−Alder Reactions:  Preparation of 2-Cobalt-Substituted 1,3-Dienes Containing <i>C</i>₂ Symmetric 2,3-Dibenzobicyclo[2.2.2]octanedione Dioxime Equatorial Ligands and Their Use in Thermal and Lewis Acid Catalyzed 4 + 2 Cycloadditions
  作者：Marcus W. Wright、Mark E. Welker

  DOI：10.1021/jo951505o

  日期：1996.1.1

  The preparation of C-2 symmetric 2,3-dibenzobicyclo[2.2.2]octanedione dioxime is reported. This ligand is then used in the preparation of a (pyridine)(glyoxime)(2)cobalt(III) chloride complex. The chloride is reduced to a cobaloxime anion which reacted with allenic electrophiles to produce (pyridine)(glyoxime)(2)cobalt-1,3-dienyl complexes. Thermal and Lewis acid catalyzed Diels-Alder reactions of these dienyl complexes as well as the complexes with glyoxime = diphenylglyoxime and dimethylglyoxime are reported. In most cases these Diels-Alder reactions are anti (exo) selective, and in many cases diastereoselectivities are >20:1. Cycloadduct demetalation reactions are also reported which preserve cycloaddition stereochemistry and provide cobalt complexes which can be recycled into the starting dienyl complex.
• DJAHANBINI, D.;CAZES, B.;GORE, J., TETRAHEDRON, 1984, 40, N 19, 3645-3655
  作者：DJAHANBINI, D.、CAZES, B.、GORE, J.

  DOI：——

  日期：——