N-[3-cyano-3-ethoxy-5,6-dimethyl-1(3H)-isobenzofuranylidene]-2-methyl-2-propanamine | 1449007-87-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: N-[3-cyano-3-ethoxy-5,6-dimethyl-1(3H)-isobenzofuranylidene]-2-methyl-2-propanamine
• CAS: 1449007-87-7
• 化学式: C₁₇H₂₂N₂O₂
• 分子量: 286.374
• InChiKey: XZNZPGAJYZCSOO-UHFFFAOYSA-N

物化性质

• 沸点：
  435.2±45.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  54.61
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-[3-cyano-3-ethoxy-5,6-dimethyl-1(3H)-isobenzofuranylidene]-2-methyl-2-propanamine 在 二异丁基氢化铝 作用下， 以 正己烷 为溶剂， 以41%的产率得到(Z)-ethyl 2-[(tert-butylimino)(cyano)methyl]-4,5-dimethylbenzoate
  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：

  异氰酸叔丁酯 、 4,5-dimethylbenzyne 、 氰基甲酸乙酯 在 palladium catalyst 作用下， 生成 N-[3-cyano-3-ethoxy-5,6-dimethyl-1(3H)-isobenzofuranylidene]-2-methyl-2-propanamine
  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

• A NOVEL THREE-COMPONENT COUPLING REACTION OF ARYNES, ISOCYANIDES, AND CYANOFORMATES: A STRAIGHTFORWARD ACCESS TO CYANO-SUBSTITUTED IMINOISOBENZOFURANS
  作者：Yasushi Nishihara、Jing Li、Shintaro Noyori、Masayuki Iwasaki、Kiyohiko Nakajima

  DOI：10.3987/com-12-s(n)77

  日期：——

  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.