2-hydroxy-3(E)-nonen-8-yne | 120544-96-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-hydroxy-3(E)-nonen-8-yne
• 英文别名: (E)-non-3-en-8-yn-2-ol
• CAS: 120544-96-9
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: MJIQNADWSKTVGW-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  2-hydroxy-3(E)-nonen-8-yne 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 溶剂黄146 、 三苯基膦 作用下， 以 苯 为溶剂， 生成 (1R,3aS,4R,8bR)-1-methyl-3-oxo-N-phenyl-1,3a,4,5,6,7,8,8b-octahydrocyclopenta[e][2]benzofuran-4-carboxamide
  参考文献：
  名称：

  Hydroxy group as a regio- and stereochemical control element for sequential metal-catalyzed and thermal cyclizations

  摘要：

  DOI：

  10.1021/jo00271a006
• 作为产物：
  描述：

  1,6-庚二炔 在 lithium aluminium tetrahydride 、 乙基溴化镁 作用下， 以 四氢呋喃 为溶剂， 反应 19.5h， 生成 2-hydroxy-3(E)-nonen-8-yne
  参考文献：
  名称：

  Pd-Catalyzed Cycloisomerization to 1,2-Dialkylidenecycloalkanes. 2. Alternative Catalyst System

  摘要：

  The mechanisms by which palladium complexes may catalyze the cycloisomerization of 1,6- and 1,7-enynes to dialkylidenecycloalkanes were probed by exploring a catalyst system different than a ligated palladium acetate which previously has proven to be successful. Although carboxylic acids showed no discernible interaction with palladium(0) complexes, this combination proved to be a powerful catalyst system to effect this cycloisomerization. The fact that the two catalyst systems do not have the same reactivity profile suggests this new catalyst system may operate by a different mechanism. Evidence supporting a pathway invoking formation of a hydridopalladium acetate followed by hydropalladation as initiation is presented. Steric and electronic effects direct the regioselectivity of the termination step to form either 1,3- or 1,4-diene products. The 1,3-diene products participate exceedingly well in Diels-Alder reactions, both inter- and intramolecularly. The presence of an oxygen substituent at the position allylic to the diene served as both a regiochemical control element for the palladium-catalyzed cycloisomerization and a diastereochemical control element for the Diels-Alder reaction. The net result of these two steps, the first of which is a catalyzed isomerization and the second an addition, is a highly efficient approach to complex polycycles in terms of both selectivity and atom economy.

  DOI：

  10.1021/ja00089a016

文献信息

• TROST, BARRY M.;LEE, DONNA C., J. ORG. CHEM., 54,(1989) N0, C. 2271-2274
  作者：TROST, BARRY M.、LEE, DONNA C.

  DOI：——

  日期：——