N-[3-butoxy-3-cyano-1(3H)-isobenzofuranylidene]-2,4,4-trimethyl-2-pentanamine | 1449007-83-3

• 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-butoxy-3-cyano-1(3H)-isobenzofuranylidene]-2,4,4-trimethyl-2-pentanamine
• 英文别名: 1-Butoxy-3-(2,4,4-trimethylpentan-2-ylimino)-2-benzofuran-1-carbonitrile；1-butoxy-3-(2,4,4-trimethylpentan-2-ylimino)-2-benzofuran-1-carbonitrile
• CAS: 1449007-83-3
• 化学式: C₂₁H₃₀N₂O₂
• 分子量: 342.481
• InChiKey: FTHROJJEBQDOMR-UHFFFAOYSA-N

物化性质

• 沸点：
  470.1±45.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 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-butoxy-3-cyano-1(3H)-isobenzofuranylidene]-2,4,4-trimethyl-2-pentanamine 在 二异丁基氢化铝 作用下， 以 正己烷 为溶剂， 以54%的产率得到(Z)-butyl 2-[cyano(2,4,4-trimethylpentan-2-ylimino)methyl]benzoate
  参考文献：
  名称：

  New Entry to the Synthesis of α-Iminonitriles by Lewis Acid Mediated Isomerization of Cyano-Substituted Iminoisobenzofurans Prepared by Palladium-Catalyzed Three-Component Coupling of Arynes, Isocyanides, and Cyanoformates

  摘要：

  A variety of alpha-iminonitriles were formed as the minor products of three-component coupling reactions of arynes, isocyanides, and cyanoformates in the presence of the cationic palladium complex [Pd(NCPh)(2)(dppf)1(BF4)(2) as the catalyst, along with cyano-substituted iminoisobenzofurans as the major products. alpha-Iminonitriles obtained from this process are hardly accessible by conventional methods. In addition, when the isolated iminoisobenzofurans were treated with diisobutylaluminum hydride (DIBAL-H) or AlMe3, the transformation of cyano-substituted iminoisobenzofurans into alpha-iminonitriles was observed.

  DOI：

  10.1021/om500408h
• 作为产物：
  描述：

  n-butyl cyanoformate 、 1,1,3,3-四甲基丁基异腈 、 2-(三甲基硅)苯基三氟甲烷磺酸盐 在 potassium fluoride 、 palladium(II)[(1,1'-bis(diphenylphosphino)ferrocene)(C₆H₅CN)2]*2BF₄ 、 18-冠醚-6 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以40%的产率得到N-[3-butoxy-3-cyano-1(3H)-isobenzofuranylidene]-2,4,4-trimethyl-2-pentanamine
  参考文献：
  名称：

  芳烃、异氰化物和氰基甲酸酯的新型三组分偶联反应：直接获得氰基取代的亚氨基异苯并呋喃

  摘要：

  Iminoisobenzofuran derivatives have been prepared in moderate yields by the palladium-catalyzed three-component coupling reaction of arynes, isocyanides, and cyanoformates. This paper is dedicated to Professor Ei-ichi Negishi on the occasion of his 77th birthday.

  DOI：

  10.3987/com-12-s(n)77

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.