2-((2R,3R,6R,Z)-3-methyl-4-((trimethylsilyl)methylene)-6-vinyl-tetrahydro-2H-pyran-2-yl)acetonitrile | 1027086-86-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 2-((2R,3R,6R,Z)-3-methyl-4-((trimethylsilyl)methylene)-6-vinyl-tetrahydro-2H-pyran-2-yl)acetonitrile
• 英文别名: 2-[(2R,3R,4Z,6R)-6-ethenyl-3-methyl-4-(trimethylsilylmethylidene)oxan-2-yl]acetonitrile
• CAS: 1027086-86-7
• 化学式: C₁₄H₂₃NOSi
• 分子量: 249.428
• InChiKey: CGFWGUYYJVWWSY-JVQALYAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.68
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-((2R,3R,6R,Z)-3-methyl-4-((trimethylsilyl)methylene)-6-vinyl-tetrahydro-2H-pyran-2-yl)acetonitrile 在 lithium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以94%的产率得到2-((2R,3R,6R)-3-methyl-4-((trimethylsilyl)methyloxirane)-6-vinyl-tetrahydro-2H-pyran-2-yl)acetonitrile
  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：

  (3R,4R,5Z,7E)-3-hydroxy-4-methyl-9-(4-nitrophenoxy)-5-((trimethylsilyl)methylene)non-7-enenitrile 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 C₅₆H₅₀N₂O₂P₂ 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 2-((2R,3R,6R,Z)-3-methyl-4-((trimethylsilyl)methylene)-6-vinyl-tetrahydro-2H-pyran-2-yl)acetonitrile 、 2-((3R,Z)-3-methyl-4-((trimethylsilyl)methylene)-6-vinyl-tetrahydro-2H-pyran-2-yl)acetonitrile
  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

文献信息

• Coupling of Alkenes and Alkynes: Synthesis of the C1−C11 and C18−C28 Fragments of Miyakolide
  作者：Barry M. Trost、Brandon L. Ashfeld

  DOI：10.1021/ol800347u

  日期：2008.5.1

  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.