1-ethoxy-3-(2,4,4-trimethylpentan-2-ylimino)-1,3-dihydronaphtho[1,2-c]furan-1-carbonitrile | 1449007-88-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 1-ethoxy-3-(2,4,4-trimethylpentan-2-ylimino)-1,3-dihydronaphtho[1,2-c]furan-1-carbonitrile
• 英文别名: 1-Ethoxy-3-(2,4,4-trimethylpentan-2-ylimino)benzo[g][2]benzofuran-1-carbonitrile；1-ethoxy-3-(2,4,4-trimethylpentan-2-ylimino)benzo[g][2]benzofuran-1-carbonitrile
• CAS: 1449007-88-8
• 化学式: C₂₃H₂₈N₂O₂
• 分子量: 364.488
• InChiKey: GKURNCAJGWFAPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 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：

  1-ethoxy-3-(2,4,4-trimethylpentan-2-ylimino)-1,3-dihydronaphtho[1,2-c]furan-1-carbonitrile 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：

  1,1,3,3-四甲基丁基异腈 、 氰基甲酸乙酯 、 三氟甲磺酸1-(三甲基硅基)-2-萘酯 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72%的产率得到1-ethoxy-3-(2,4,4-trimethylpentan-2-ylimino)-1,3-dihydronaphtho[1,2-c]furan-1-carbonitrile
  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

• 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
  作者：Jing Li、Shintaro Noyori、Kiyohiko Nakajima、Yasushi Nishihara

  DOI：10.1021/om500408h

  日期：2014.7.14

  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.
• 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.
• 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.