Hept-6-ynoic acid cyano-(3-propyl-oxetan-3-yl)-methyl ester | 121317-95-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Hept-6-ynoic acid cyano-(3-propyl-oxetan-3-yl)-methyl ester
• 英文别名: [Cyano-(3-propyloxetan-3-yl)methyl] hept-6-ynoate
• CAS: 121317-95-1
• 化学式: C₁₅H₂₁NO₃
• 分子量: 263.337
• InChiKey: FOWMNHXHVHRPRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Hept-6-ynoic acid cyano-(3-propyl-oxetan-3-yl)-methyl ester 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 生成 1-(Hex-5-ynyl)-4-propyl-2,6,7-trioxabicyclo[2.2.2]octane-3-carbonitrile
  参考文献：
  名称：

  Insecticidal 1-(alkynylalkyl)-3-cyano-2,6,7-trioxabicyclo[2.2.2]octanes

  摘要：

  The high insecticidal activity and potency at the insect GABA-gated chloride channel of 4-alkyl-3-cyano-2,6,7-trioxabicyclo[2.2.2]octanes with the 1-(4-ethynylphenyl) substituent is also achieved with the corresponding l-(hex-5-ynyl) analogs. Conceptually the four-methylene linkage resembles the spatial characteristics of a phenyl ring and allows the ethynyl group to occupy the same area of receptor space as when attached at the 4-position of an aryl moiety. This is the first example of chloride channel blockers with the ability to replace a phenyl group by a conformationally flexible alkyl linkage and retain a significant portion of the activity.

  DOI：

  10.1021/jf00031a020
• 作为产物：
  描述：

  3-hydroxymethyl-3-n-propyl oxetane 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 乙醚 、 水 为溶剂， 生成 Hept-6-ynoic acid cyano-(3-propyl-oxetan-3-yl)-methyl ester
  参考文献：
  名称：

  Insecticidal 1-(alkynylalkyl)-3-cyano-2,6,7-trioxabicyclo[2.2.2]octanes

  摘要：

  The high insecticidal activity and potency at the insect GABA-gated chloride channel of 4-alkyl-3-cyano-2,6,7-trioxabicyclo[2.2.2]octanes with the 1-(4-ethynylphenyl) substituent is also achieved with the corresponding l-(hex-5-ynyl) analogs. Conceptually the four-methylene linkage resembles the spatial characteristics of a phenyl ring and allows the ethynyl group to occupy the same area of receptor space as when attached at the 4-position of an aryl moiety. This is the first example of chloride channel blockers with the ability to replace a phenyl group by a conformationally flexible alkyl linkage and retain a significant portion of the activity.

  DOI：

  10.1021/jf00031a020

文献信息

• Pesticidal compounds
  申请人：ROUSSEL UCLAF

  公开号：EP0300797B1

  公开（公告）日：1995-10-04
• Insecticidal 1-(alkynylalkyl)-3-cyano-2,6,7-trioxabicyclo[2.2.2]octanes
  作者：Ian H. Smith、Timothy C. Budd、Jill. Sills、John E. Casida

  DOI：10.1021/jf00031a020

  日期：1993.7

  The high insecticidal activity and potency at the insect GABA-gated chloride channel of 4-alkyl-3-cyano-2,6,7-trioxabicyclo[2.2.2]octanes with the 1-(4-ethynylphenyl) substituent is also achieved with the corresponding l-(hex-5-ynyl) analogs. Conceptually the four-methylene linkage resembles the spatial characteristics of a phenyl ring and allows the ethynyl group to occupy the same area of receptor space as when attached at the 4-position of an aryl moiety. This is the first example of chloride channel blockers with the ability to replace a phenyl group by a conformationally flexible alkyl linkage and retain a significant portion of the activity.