(Z)-12-oxododec-2-enenitrile | 1236376-98-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-12-oxododec-2-enenitrile
• CAS: 1236376-98-9
• 化学式: C₁₂H₁₉NO
• 分子量: 193.289
• InChiKey: KKBMOYWEKMTIGB-CLFYSBASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  10-十一烯醛 、 丙烯腈 在 C₃₁H₃₈Cl₄N₂ORuSn 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 (Z)-12-oxododec-2-enenitrile 、 (E)-12-oxododec-2-enenitrile
  参考文献：
  名称：

  Alkylidene-Ruthenium-Tin Catalysts for the Formation of Fatty Nitriles and Esters via Cross-Metathesis of Plant Oil Derivatives

  摘要：

  The reaction of SnCl2 with the Ru-Cl bond of the Grubbs I catalyst RuCl2(=CHPh)(PCy3)(2) (1) gives the complex {[Ru(=CHPh)(SnCl3)(PCy3)](2)(mu-Cl)(3)}(-)[HPCy3](+) (2), but containing two diethyl ether solvate molecules. The formal insertion of SnCl2 into one Ru-Cl bond of the Hoveyda II catalyst RuCl2(=CH-C6H4OPri)H(2)IMes) (3) (H(2)IMes = N,N'-dimesityl-4,5-dihydroimidazol-2-ylidene) results in formation of the new complex RuCl(SnCl3)(=CH-C6H4OPri)(H(2)IMes) (4). The X-ray analyses of 2 and 4 show the presence of very short Ru-Sn bonds (2.5834(9) angstrom mean bond for 2 and 2.5925(12) angstrom for 4) and the retention of short Ru=C bonds (1.895(10) and 1.825(8) angstrom, respectively). Complex 4 shows an excellent catalytic activity for the cross-metathesis of plant oil derivatives, the C11 omega-unsaturated ester and aldehyde and the unsaturated C18 diester with acrylonitrile, and a good activity for their cross-metathesis with methyl acrylate. Good to excellent yield of alpha,omega-bifunctional compounds, precursors of polyesters and polyamides, were obtained. Complex 2 shows catalytic activity for the self-metathesis of C11 omega-unsaturated aldehyde at low concentration to produce C20 alpha,omega-dialdehyde.

  DOI：

  10.1021/om100372b

文献信息

• Alkylidene-Ruthenium-Tin Catalysts for the Formation of Fatty Nitriles and Esters via Cross-Metathesis of Plant Oil Derivatives
  作者：Xiaowei Miao、Anton Blokhin、Alexandr Pasynskii、Sergey Nefedov、Sergey N. Osipov、Thierry Roisnel、Christian Bruneau、Pierre H. Dixneuf

  DOI：10.1021/om100372b

  日期：2010.11.8

  The reaction of SnCl2 with the Ru-Cl bond of the Grubbs I catalyst RuCl2(=CHPh)(PCy3)(2) (1) gives the complex [Ru(=CHPh)(SnCl3)(PCy3)](2)(mu-Cl)(3)}(-)[HPCy3](+) (2), but containing two diethyl ether solvate molecules. The formal insertion of SnCl2 into one Ru-Cl bond of the Hoveyda II catalyst RuCl2(=CH-C6H4OPri)H(2)IMes) (3) (H(2)IMes = N,N'-dimesityl-4,5-dihydroimidazol-2-ylidene) results in formation of the new complex RuCl(SnCl3)(=CH-C6H4OPri)(H(2)IMes) (4). The X-ray analyses of 2 and 4 show the presence of very short Ru-Sn bonds (2.5834(9) angstrom mean bond for 2 and 2.5925(12) angstrom for 4) and the retention of short Ru=C bonds (1.895(10) and 1.825(8) angstrom, respectively). Complex 4 shows an excellent catalytic activity for the cross-metathesis of plant oil derivatives, the C11 omega-unsaturated ester and aldehyde and the unsaturated C18 diester with acrylonitrile, and a good activity for their cross-metathesis with methyl acrylate. Good to excellent yield of alpha,omega-bifunctional compounds, precursors of polyesters and polyamides, were obtained. Complex 2 shows catalytic activity for the self-metathesis of C11 omega-unsaturated aldehyde at low concentration to produce C20 alpha,omega-dialdehyde.