10-(2-Butyl-cycloprop-1-enyl)-decanenitrile | 162142-76-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 10-(2-Butyl-cycloprop-1-enyl)-decanenitrile
• 英文别名: 10-(2-Butylcyclopropen-1-yl)decanenitrile；10-(2-butylcyclopropen-1-yl)decanenitrile
• CAS: 162142-76-9
• 化学式: C₁₇H₂₉N
• 分子量: 247.424
• InChiKey: CBAWYBDZJLNCRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  18
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  10-(2-Butyl-cycloprop-1-enyl)-decanenitrile 生成 10-(2-Butyl-cycloprop-1-enyl)-decanoic acid
  参考文献：
  名称：

  Structure−Activity Relationships of Cyclopropene Compounds, Inhibitors of Pheromone Biosynthesis in Bombyx mori

  摘要：

  According to the synthetic route for 11,12-methylenehexadec-11-enoic acid [10-(2-butyl-1-cyclopropenyl)decanoic acid] and the amide, their related cyclopropene compounds, which possessed a propene ring at the 7,8-, 9,10-, or 13,14-position in a C-16 chain and the 11,12-position in a C-14 or C-18 chain, were synthesized via the corresponding 1-alkyl-1,2,2-tribromocyclopropane. Their activities as biosynthetic inhibitors of bombykol [(10E,12Z)-10,12-hexadecadien-1-ol; sex pheromone of the silkworm moth Bombyx mori L.] were measured with virgin female silkworm moths in vivo. The 7,8-methylene compounds were inactive even at the dose of 10 mu g/gland, but other compounds at 1 mu g/gland inhibited the conversion of [16,16, 16-H-2(3)]hexadecanoic acid to bombykol to some extent. Each amide showed stronger inhibitory activity than the corresponding acid, and the 11,12-methylene amide with a C-16 chain was the strongest (I-50 = 0.016 mu g/gland) among the tested compounds. Furthermore, experiments comparing the incorporation of [1-C-14]hexadecanoic acid into bombykol and another alcohol component in the pheromone gland, (Z)-11-hexadecen-1-ol, suggested that the all-desaturation was blocked by 9,10- and 11,12-methylene compounds and the subsequent Delta 10,- 12-desaturation by 11,12- and 13,14-methylene compounds.

  DOI：

  10.1021/jf950757n
• 作为产物：
  描述：

  2-溴己-1-烯 在 六甲基磷酰三胺 、 sodium hydroxide 、 正丁基锂 、 十六烷基三甲基溴化铵 作用下， 以 水 、 丙酮 为溶剂， 反应 16.0h， 生成 10-(2-Butyl-cycloprop-1-enyl)-decanenitrile
  参考文献：
  名称：

  Structure−Activity Relationships of Cyclopropene Compounds, Inhibitors of Pheromone Biosynthesis in Bombyx mori

  摘要：

  According to the synthetic route for 11,12-methylenehexadec-11-enoic acid [10-(2-butyl-1-cyclopropenyl)decanoic acid] and the amide, their related cyclopropene compounds, which possessed a propene ring at the 7,8-, 9,10-, or 13,14-position in a C-16 chain and the 11,12-position in a C-14 or C-18 chain, were synthesized via the corresponding 1-alkyl-1,2,2-tribromocyclopropane. Their activities as biosynthetic inhibitors of bombykol [(10E,12Z)-10,12-hexadecadien-1-ol; sex pheromone of the silkworm moth Bombyx mori L.] were measured with virgin female silkworm moths in vivo. The 7,8-methylene compounds were inactive even at the dose of 10 mu g/gland, but other compounds at 1 mu g/gland inhibited the conversion of [16,16, 16-H-2(3)]hexadecanoic acid to bombykol to some extent. Each amide showed stronger inhibitory activity than the corresponding acid, and the 11,12-methylene amide with a C-16 chain was the strongest (I-50 = 0.016 mu g/gland) among the tested compounds. Furthermore, experiments comparing the incorporation of [1-C-14]hexadecanoic acid into bombykol and another alcohol component in the pheromone gland, (Z)-11-hexadecen-1-ol, suggested that the all-desaturation was blocked by 9,10- and 11,12-methylene compounds and the subsequent Delta 10,- 12-desaturation by 11,12- and 13,14-methylene compounds.

  DOI：

  10.1021/jf950757n

文献信息

• Structure−Activity Relationships of Cyclopropene Compounds, Inhibitors of Pheromone Biosynthesis in <i>Bombyx mori</i>
  作者：Tetsu Ando、Ryuta Ohno、Kazuhisa Ikemoto、Masanobu Yamamoto

  DOI：10.1021/jf950757n

  日期：1996.1.1

  According to the synthetic route for 11,12-methylenehexadec-11-enoic acid [10-(2-butyl-1-cyclopropenyl)decanoic acid] and the amide, their related cyclopropene compounds, which possessed a propene ring at the 7,8-, 9,10-, or 13,14-position in a C-16 chain and the 11,12-position in a C-14 or C-18 chain, were synthesized via the corresponding 1-alkyl-1,2,2-tribromocyclopropane. Their activities as biosynthetic inhibitors of bombykol [(10E,12Z)-10,12-hexadecadien-1-ol; sex pheromone of the silkworm moth Bombyx mori L.] were measured with virgin female silkworm moths in vivo. The 7,8-methylene compounds were inactive even at the dose of 10 mu g/gland, but other compounds at 1 mu g/gland inhibited the conversion of [16,16, 16-H-2(3)]hexadecanoic acid to bombykol to some extent. Each amide showed stronger inhibitory activity than the corresponding acid, and the 11,12-methylene amide with a C-16 chain was the strongest (I-50 = 0.016 mu g/gland) among the tested compounds. Furthermore, experiments comparing the incorporation of [1-C-14]hexadecanoic acid into bombykol and another alcohol component in the pheromone gland, (Z)-11-hexadecen-1-ol, suggested that the all-desaturation was blocked by 9,10- and 11,12-methylene compounds and the subsequent Delta 10,- 12-desaturation by 11,12- and 13,14-methylene compounds.