4-methylenenon-8-ynal | 917989-36-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methylenenon-8-ynal
• 英文别名: 4-Methylidenenon-8-ynal
• CAS: 917989-36-7
• 化学式: C₁₀H₁₄O
• 分子量: 150.221
• InChiKey: DNIIZQCJUZFVHY-UHFFFAOYSA-N

物化性质

• 沸点：
  224.7±33.0 °C(Predicted)
• 密度：
  0.885±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-methylenenon-8-ynal 、 甲氧羰基亚甲基三苯基正膦 以 二氯甲烷 为溶剂， 反应 10.0h， 以72%的产率得到(E)-methyl 6-methyleneundec-2-en-10-ynoate
  参考文献：
  名称：

  Total Synthesis of Peroxyacarnoates A and D:  Metal-Mediated Couplings as a Convergent Approach to Polyunsaturated Peroxides

  摘要：

  The first syntheses of peroxyacarnoates A and D, members of a family of enyne-containing alkoxydioxanes, have been achieved on the basis of chemoselective ozonolysis within a polyunsaturated framework and Pd-mediated cross-couplings of a functionalized 1,2-dioxane.

  DOI：

  10.1021/ol050291m
• 作为产物：
  描述：

  己基-5-壬基氯 在 盐酸 、 copper(I) bromide dimethylsulfide complex 、 双(三甲基硅烷基)氨基钾 、 magnesium 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 反应 10.5h， 生成 4-methylenenon-8-ynal
  参考文献：
  名称：

  Total Synthesis of Peroxyacarnoates A and D:  Metal-Mediated Couplings as a Convergent Approach to Polyunsaturated Peroxides

  摘要：

  The first syntheses of peroxyacarnoates A and D, members of a family of enyne-containing alkoxydioxanes, have been achieved on the basis of chemoselective ozonolysis within a polyunsaturated framework and Pd-mediated cross-couplings of a functionalized 1,2-dioxane.

  DOI：

  10.1021/ol050291m

文献信息

• An approach to triquinane synthesis using the Pauson–Khand reaction
  作者：Marie E. Krafft、Graham M. Kyne、Chitaru Hirosawa、Peter Schmidt、Khalil A. Abboud、Nathalie L'Helias

  DOI：10.1016/j.tet.2006.09.022

  日期：2006.12

  Tricyclic skeletons have been generated from acyclic enyne precursors by using an intramolecular Pauson-Khand reaction in combination with aldol, Michael and alkylation reactions. (c) 2006 Elsevier Ltd. All rights reserved.
• Asymmetric synthesis of 1,2-dioxanes: approaches to the peroxyplakoric acids
  作者：Chunping Xu、Chris Schwartz、Joseph Raible、Patrick H. Dussault

  DOI：10.1016/j.tet.2009.09.068

  日期：2009.11

  The stereospecific intramolecular alkylation of a hydroperoxyacetal provides the basis for the first asymmetric synthesis of the dioxane propionate core of the peroxyplakorates. Chemoselective hydrometallation of an alkyne in the presence of a peroxide is used to introduce a synthon for the polyunsaturated side chains of the peroxyplakorates. The route suggests a general solution for the 1,2-dioxane unit in many peroxide natural products. (C) 2009 Elsevier Ltd. All rights reserved.
• Total Synthesis of Peroxyacarnoates A and D:  Metal-Mediated Couplings as a Convergent Approach to Polyunsaturated Peroxides
  作者：Chunping Xu、Joseph M. Raible、Patrick H. Dussault

  DOI：10.1021/ol050291m

  日期：2005.6.1

  The first syntheses of peroxyacarnoates A and D, members of a family of enyne-containing alkoxydioxanes, have been achieved on the basis of chemoselective ozonolysis within a polyunsaturated framework and Pd-mediated cross-couplings of a functionalized 1,2-dioxane.