N-[3-cyano-3-ethoxy-1(3H)-isobenzofuranylidene]-2,4,4-trimethyl-2-pentanamine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: N-[3-cyano-3-ethoxy-1(3H)-isobenzofuranylidene]-2,4,4-trimethyl-2-pentanamine
• 英文别名: 1-Ethoxy-3-(2,4,4-trimethylpentan-2-ylimino)-2-benzofuran-1-carbonitrile；1-ethoxy-3-(2,4,4-trimethylpentan-2-ylimino)-2-benzofuran-1-carbonitrile
• 化学式: C₁₉H₂₆N₂O₂
• 分子量: 314.428
• InChiKey: SKZXRMGRBLEKAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  54.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[3-cyano-3-ethoxy-1(3H)-isobenzofuranylidene]-2,4,4-trimethyl-2-pentanamine 在 三(五氟苯基)硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 1-Phenyl-3-(2,4,4-trimethylpentan-2-ylimino)-2-benzofuran-1-carbonitrile
  参考文献：
  名称：

  Skeletal Rearrangement of Cyano-Substituted Iminoisobenzofurans into Alkyl 2-Cyanobenzoates Catalyzed by B(C₆F₅)₃

  摘要：

  An efficient method for the direct conversion of cyano-substituted iminoisobenzofurans into their corresponding alkyl 2-cyanobenzoates has been developed. This transformation proceeds via cleavage of C-C, C-O, and C-N bonds in starting iminoisobenzofurans. DFT study revealed that intermediate a-iminonitriles are produced in situ via C-C bond formation between 2-iminium benzoates and a cyanide ion. Generation of isocyanide as the byproduct in a more thermodynamic manner in DFT calculations also supports the experimental results.

  DOI：

  10.1021/ol5026519
• 作为产物：
  描述：

  N-[3-cyano-3-methoxy-1(3H)-isobenzofuranylidene]-2,4,4-trimethyl-2-pentanamine 在 三(五氟苯基)硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 N-[3-cyano-3-ethoxy-1(3H)-isobenzofuranylidene]-2,4,4-trimethyl-2-pentanamine
  参考文献：
  名称：

  Skeletal Rearrangement of Cyano-Substituted Iminoisobenzofurans into Alkyl 2-Cyanobenzoates Catalyzed by B(C₆F₅)₃

  摘要：

  An efficient method for the direct conversion of cyano-substituted iminoisobenzofurans into their corresponding alkyl 2-cyanobenzoates has been developed. This transformation proceeds via cleavage of C-C, C-O, and C-N bonds in starting iminoisobenzofurans. DFT study revealed that intermediate a-iminonitriles are produced in situ via C-C bond formation between 2-iminium benzoates and a cyanide ion. Generation of isocyanide as the byproduct in a more thermodynamic manner in DFT calculations also supports the experimental results.

  DOI：

  10.1021/ol5026519

文献信息

• Skeletal Rearrangement of Cyano-Substituted Iminoisobenzofurans into Alkyl 2-Cyanobenzoates Catalyzed by B(C₆F₅)₃
  作者：Jing Li、Yasuhiro Okuda、Jiaji Zhao、Seiji Mori、Yasushi Nishihara

  DOI：10.1021/ol5026519

  日期：2014.10.3

  An efficient method for the direct conversion of cyano-substituted iminoisobenzofurans into their corresponding alkyl 2-cyanobenzoates has been developed. This transformation proceeds via cleavage of C-C, C-O, and C-N bonds in starting iminoisobenzofurans. DFT study revealed that intermediate a-iminonitriles are produced in situ via C-C bond formation between 2-iminium benzoates and a cyanide ion. Generation of isocyanide as the byproduct in a more thermodynamic manner in DFT calculations also supports the experimental results.