4,4-dimethyl-6-hydroxy-1-tridecen-7,12-diyne | 116377-64-1

• 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: 4,4-dimethyl-6-hydroxy-1-tridecen-7,12-diyne
• 英文别名: 4,4-dimethyltridec-1-en-7,12-diyn-6-ol
• CAS: 116377-64-1
• 化学式: C₁₅H₂₂O
• 分子量: 218.339
• InChiKey: XSQUIADJCREJOL-UHFFFAOYSA-N

物化性质

• 沸点：
  324.4±42.0 °C(Predicted)
• 密度：
  0.924±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.15
• 重原子数：
  16.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4,4-dimethyl-6-hydroxy-1-tridecen-7,12-diyne 在 T406石油添加剂 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 lithium aluminium tetrahydride 、 四丁基氟化铵 、 溶剂黄146 、 三苯基膦 作用下， 以 四氢呋喃 、 甲苯 、 苯 为溶剂， 生成 (5aR,9S,9aR)-7,7-dimethyl-1,2,3,4,5,5a,6,8,9,9a-decahydrocyclopenta[a]naphthalen-9-ol
  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 、 3,3-二甲基-5-己醛 在 乙基溴化镁 作用下， 生成 4,4-dimethyl-6-hydroxy-1-tridecen-7,12-diyne
  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

• A catalytic reductive cyclization of 1,6-diynes
  作者：Barry M. Trost、Donna C. Lee

  DOI：10.1021/ja00229a073

  日期：1988.10

  Catalyse par le complexe (dba) 3 Pd 2 •CHCl 3 (dba=dibenzylideneacetone). Preparation de dialkylidene-1,2 cyclopentanes

  催化par le complexe (dba) 3 Pd 2 •CHCl 3 (dba=二亚苄基丙酮)。二亚烷基-1,2环戊烷的制备
• 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：——
• TROST, BARRY M.;LEE, DONNA C., J. AMER. CHEM. SOC., 110,(1988) N 21, C. 7255-7258
  作者：TROST, BARRY M.、LEE, DONNA C.

  DOI：——

  日期：——