(4R,5R)-Heptadec-1-yne-4,5-diol | 256447-43-5

• 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: (4R,5R)-Heptadec-1-yne-4,5-diol
• CAS: 256447-43-5
• 化学式: C₁₇H₃₂O₂
• 分子量: 268.44
• InChiKey: NDKLVOVLFTVVEB-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  19
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4R,5R)-Heptadec-1-yne-4,5-diol 在 (cyclooctadienyl)(cyclopentadienyl)ruthenium chloride N-羟基丁二酰亚胺 、 三(2-呋喃基)膦 、 四丁基溴化铵 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 以62%的产率得到(5R)-5-[(1R)-1-羟基十三烷基]四氢呋喃-2-酮
  参考文献：
  名称：

  Ruthenium-Catalyzed Cycloisomerization−Oxidation of Homopropargyl Alcohols. A New Access to γ-Butyrolactones

  摘要：

  Vinylidenemetal species, which readily form from terminal alkynes under mild conditions, have rarely been utilized as reactive intermediates in a catalytic cycle. The conversion of homopropargyl alcohols via such intermediates to metal-complexed oxacarbenes led to the development of an "oxidant" compatible with a ruthenium complex capable of performing the cycloisomerization, that would convert them to lactones. None of the oxidants known to stoichiometrically convert isolated metallooxacarbenes to esters are effective. The unconventional "oxidants", N-hydroxyimides, proved to be capable of effecting the desired transformation, with N-hydroxysuccinimide being the "oxidant" of choice. The procedure of choice employs cyclopentadienyl (1,4-cyclooctadiene) ruthenium chloride and trifuryl phosphine as the precatalyst in the presence of tetra-n-butylammonium bromide or hexafluorophosphate with N-hydroxysuccinimide as the oxidant in DMF-water at 95 degrees. In this way, a wide diversity of homopropargyl alcohols were converted to gamma-butyrolactones with excellent chemoselectivity. Lactones synthesized include an intermediate toward a platelet aggregation inhibitor, a fruit flavor principle, an inhibitor of binding of phorbol esters to PKC-alpha, a tobacco constituent, a wood constituent (quercus lactone), an aldosterone antagonist (spironolactone) precursor, and an acetogenin known for pesticidal and antitumor activities (muricatacin).

  DOI：

  10.1021/ja992013m
• 作为产物：
  描述：

  1-bromo-2(E)-pentadecene 在 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 copper(l) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 生成 (4R,5R)-Heptadec-1-yne-4,5-diol
  参考文献：
  名称：

  Ruthenium-Catalyzed Cycloisomerization−Oxidation of Homopropargyl Alcohols. A New Access to γ-Butyrolactones

  摘要：

  Vinylidenemetal species, which readily form from terminal alkynes under mild conditions, have rarely been utilized as reactive intermediates in a catalytic cycle. The conversion of homopropargyl alcohols via such intermediates to metal-complexed oxacarbenes led to the development of an "oxidant" compatible with a ruthenium complex capable of performing the cycloisomerization, that would convert them to lactones. None of the oxidants known to stoichiometrically convert isolated metallooxacarbenes to esters are effective. The unconventional "oxidants", N-hydroxyimides, proved to be capable of effecting the desired transformation, with N-hydroxysuccinimide being the "oxidant" of choice. The procedure of choice employs cyclopentadienyl (1,4-cyclooctadiene) ruthenium chloride and trifuryl phosphine as the precatalyst in the presence of tetra-n-butylammonium bromide or hexafluorophosphate with N-hydroxysuccinimide as the oxidant in DMF-water at 95 degrees. In this way, a wide diversity of homopropargyl alcohols were converted to gamma-butyrolactones with excellent chemoselectivity. Lactones synthesized include an intermediate toward a platelet aggregation inhibitor, a fruit flavor principle, an inhibitor of binding of phorbol esters to PKC-alpha, a tobacco constituent, a wood constituent (quercus lactone), an aldosterone antagonist (spironolactone) precursor, and an acetogenin known for pesticidal and antitumor activities (muricatacin).

  DOI：

  10.1021/ja992013m