(3R,4R)-3-hydroxy-4-methyl-6-(trimethylsilyl)hex-5-ynenitrile | 1027086-76-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4R)-3-hydroxy-4-methyl-6-(trimethylsilyl)hex-5-ynenitrile
• CAS: 1027086-76-5
• 化学式: C₁₀H₁₇NOSi
• 分子量: 195.337
• InChiKey: ORMPFNQVZBKNDZ-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.78
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  44.02
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (3R,4R)-3-hydroxy-4-methyl-6-(trimethylsilyl)hex-5-ynenitrile 、 1-(but-3-en-1-yloxy)-4-nitrobenzene 在 cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate 作用下， 以 丙酮 为溶剂， 以10%的产率得到(3R,4R,5Z,7E)-3-hydroxy-4-methyl-9-(4-nitrophenoxy)-5-((trimethylsilyl)methylene)non-7-enenitrile
  参考文献：
  名称：

  Coupling of Alkenes and Alkynes: Synthesis of the C1−C11 and C18−C28 Fragments of Miyakolide

  摘要：

  A transition metal-mediated, atom-economical approach toward the crucial A and D rings of miyakolide is described. A Pd-catalyzed alkyne-alkyne coupling/6-endo-dig cyclization is employed to assemble the A ring fragment. The key D ring pyran is constructed utilizing an Ru-catalyzed alkene-alkyne coupling followed by a Pd-catalyzed allylic alkylation to establish the all-cis stereochemistry.

  DOI：

  10.1021/ol800347u
• 作为产物：
  描述：

  trimethyl((R)-3-((S)-oxiran-2-yl)but-1-ynyl)silane 、 二乙基氰化铝 以 四氢呋喃 、 甲苯 为溶剂， 以78%的产率得到(3R,4R)-3-hydroxy-4-methyl-6-(trimethylsilyl)hex-5-ynenitrile
  参考文献：
  名称：

  Coupling of Alkenes and Alkynes: Synthesis of the C1−C11 and C18−C28 Fragments of Miyakolide

  摘要：

  A transition metal-mediated, atom-economical approach toward the crucial A and D rings of miyakolide is described. A Pd-catalyzed alkyne-alkyne coupling/6-endo-dig cyclization is employed to assemble the A ring fragment. The key D ring pyran is constructed utilizing an Ru-catalyzed alkene-alkyne coupling followed by a Pd-catalyzed allylic alkylation to establish the all-cis stereochemistry.

  DOI：

  10.1021/ol800347u