2-heptynenitrile | 1972-96-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-heptynenitrile
• 英文别名: 1-Cyan-hex-1-in；2-Heptinnitril；Heptin-(2)-nitril-(1)；Hept-2-in-saeurenitril；hept-2-ynenitrile；Hept-2-innitril
• CAS: 1972-96-9
• 化学式: C₇H₉N
• 分子量: 107.155
• InChiKey: LQKVSUAZSZDGDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-heptynenitrile 、 苯硼酸 在 copper (I) acetate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以83%的产率得到E-3-phenylheptenitrile
  参考文献：
  名称：

  铜催化3-芳基-2-丙腈与芳基硼酸的立体选择性加氢芳基化

  摘要：

  Abstractmagnified imageThe selective synthesis of 3,3‐diarylacrylonitriles has been achieved by copper‐catalyzed hydroarylation of 3‐aryl‐2‐propynenitriles with arylboronic acids. The starting cyanoalkynes were efficiently prepared from the appropriate aromatic aldehydes and diethyl cyanomethylphosphonate in two steps. The hydroarylation of the obtained cyanoalkyne substrates proceeded in methanol at ambient temperature to produce 3,3‐diarylacrylonitriles in good to high yields with excellent syn selectivity. The present method was successfully applied to the regiospecific synthesis of both stereoisomers of CC‐5079, which was recently reported as a potent anticancer drug.

  DOI：

  10.1002/adsc.200900067
• 作为产物：
  描述：

  (hex-1-ynyl)magnesium bromide 、 氯化氰 在 乙醚 作用下， 生成 2-heptynenitrile
  参考文献：
  名称：

  The Dielectric Properties of Acetylenic Compounds. VII. Alkyl- and Arylpropiol-nitriles. Resonance in the Acetylene Triple Bond

  摘要：

  DOI：

  10.1021/ja01284a052

文献信息

• Conjugate Addition Reactions of α-Aminoalkylcuprates with α,β-Alkenyl-, α,β-Alkynyl-, α,β−β,γ-Allenyl-, and α,β−γ,δ-Dienyl Carboxylic Acid Derivatives, Nitriles, and Sulfoxides
  作者：R. Karl Dieter、Kai Lu、Sadanandan E. Velu

  DOI：10.1021/jo0056038

  日期：2000.12.1

  participate in 1,4-addition reactions with alpha, beta-unsaturated esters, thiol esters, imides, and nitriles in poor to excellent yields depending upon the electron-withdrawing substituent and the substitution pattern of the unsaturated substrate. These reagents also undergo conjugate addition reactions with alpha,beta-alkynyl esters, sulfoxides, and nitriles and with alpha,beta-beta,gamma-unsaturated allenyl

  由α-硫代氨基甲酸酯和CuCN.2LiCl制备的α-氨基烷基铜酸酯参与与α，β-不饱和酯，硫醇酯，酰亚胺和腈的1,4-加成反应，取决于吸电子取代基和不饱和底物的取代模式。这些试剂还与α，β-炔基酯，亚砜和腈以及α，β-β，γ-不饱和烯基酯进行共轭加成反应。在α-氨基烷基铜酸酯与烯丙基酯的共轭加成中实现了优异的立体控制，而立体选择性差导致向炔基衍生物的共轭加成。炔基加合物的脱保护和环化反应可得到吡咯烷-2-酮，
• Synthesis of (Z)-3-aryloxy-acrylonitriles, (E)-3-aryloxy-acrylonitriles and 3-cyanobenzofurans through the sequential reactions of phenols with propiolonitriles
  作者：Wei Zhou、Yicheng Zhang、Pinhua Li、Lei Wang

  DOI：10.1039/c2ob25969a

  日期：——

  A Na2CO3-promoted addition of phenols to propiolonitriles generated (Z)-3-aryloxy-acrylonitriles in nearly quantitative yields with exclusively Z-isomers, and a DABCO-promoted addition reaction of phenols with propiolonitriles afforded mainly (E)-3-aryloxy-acrylonitriles with high yields. The obtained (E)-3-aryloxy-acrylonitriles underwent intramolecular cyclization to give 3-cyanobenzofurans in good yields through palladium-catalyzed direct C–H bond functionalization.

  Na2CO3催化下，酚类与丙腈的加成反应生成了几乎定量产率的(Z)-3-芳氧丙烯腈，且只有Z异构体。而在DABCO催化下，酚类与丙腈的加成反应主要生成了高产率的(E)-3-芳氧丙烯腈。所获得的(E)-3-芳氧丙烯腈通过钯催化的直接C–H键官能化反应发生分子内环化，生成了3-氰基苯并呋喃，产率良好。
• Shirakawa, Eiji; Yoshida, Hiroto; Nakao, Yoshiaki, Organic Letters, 2000, vol. 2, # 15, p. 2208 - 2212
  作者：Shirakawa, Eiji、Yoshida, Hiroto、Nakao, Yoshiaki、Hiyama, Tamejiro

  DOI：——

  日期：——
• van der Welle,R.A.; Brandsma,L., Recueil des Travaux Chimiques des Pays-Bas, 1973, vol. 92, p. 667 - 672
  作者：van der Welle,R.A.、Brandsma,L.

  DOI：——

  日期：——
• WESTMIJZE H.; KLEIJN H.; VERMEER P., SYNTHESIS, 1979, NO 6, 430-431
  作者：WESTMIJZE H.、 KLEIJN H.、 VERMEER P.

  DOI：——

  日期：——