1-(Pent-4-ynyl)-4-propyl-2,6,7-trioxabicyclo[2.2.2]octane-3-carbonitrile | 121317-22-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(Pent-4-ynyl)-4-propyl-2,6,7-trioxabicyclo[2.2.2]octane-3-carbonitrile
• 英文别名: 4-Pent-4-ynyl-1-propyl-3,5,8-trioxabicyclo(2.2.2)octane-7-carbonitrile；1-pent-4-ynyl-4-propyl-2,6,7-trioxabicyclo[2.2.2]octane-3-carbonitrile
• CAS: 121317-22-4
• 化学式: C₁₄H₁₉NO₃
• 分子量: 249.31
• InChiKey: JJZZBQFVYSVFKJ-UHFFFAOYSA-N

物化性质

• 沸点：
  349.3±42.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  51.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  己基-5-壬基氯 在 三氟化硼乙醚 作用下， 以 乙醚 、 二氯甲烷 、 水 为溶剂， 生成 1-(Pent-4-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

文献信息

• Pesticidal compounds
  申请人：The Wellcome Foundation Limited

  公开号：US05116862A1

  公开（公告）日：1992-05-26

  The present invention provides a class of novel substituted bicyclooctanes which have pesticidal activity, particularly against arthropod pests. Pesticidal formulations containing the compounds of the formula (I), their use in the control of pests and methods for their preparation are also disclosed.

  本发明提供了一类具有杀虫活性的新型取代双环辛烷化合物，特别针对节肢动物害虫。还公开了含有式(I)化合物的杀虫配方，以及它们在害虫控制中的使用方法和制备方法。
• Heterobicycloalkanes as pesticidal compounds
  申请人：Roussel Uclaf

  公开号：US05466710A1

  公开（公告）日：1995-11-14

  The present invention provides a class of substituted bicyclooctanes of formula ##STR1## wherein R is a C.sub.2-10 non-aromatic hydrocarbyl optionally substituted by cyano, halo, C.sub.1-4 alkoxy, C.sub.1-4 haloalkoxy or S(O).sub.m R.sup.3 ; R.sup.1 and r.sup.2 are independently hydrogen, halo, a C.sub.1-3 aliphatic group optionally substituted, S(O).sub.m,R.sup.4, or R.sup.1 and R.sup.2 and the carbon atoms to which they are attached form a C.sub.5-7 carbocyclic ring optionally substituted by halo, or a C.sub.1-3 aliphatic or alkoxy group; A-X is a group: (i) A'C.tbd.CX in which A' is a C.sub.3-6 alkyl, alkenyl or alkynyl or a C.sub.3-10 cycloalkyl or cycloalkenyl group all optionally containing one to three hetero atoms. (ii) BX in which B is a group (CH.sub.2).sub.2 O or (CH.sub.2).sub.2 S(O).sub.n or a C.sub.2-6 aliphatic chain optionally containing one or two oxygen or sulphur atoms and/or double bonds and optionally further substituted; X is hydrogen, halo, SiR.sup.5 R.sup.6 R.sup.7 or SnR.sup.5 R.sup.6 R.sup.7 or CR.sup.8 R.sup.9 R.sup.10 ; Y and Y.sup.1 are independentaly oxygen or S(O).sub.n' and Z is CH.sub.2 S(O).sub.n " provided that when A does not contain a C.tbd.C fragment, X is a group CR.sup.8 R.sup.9 R.sup.10. The compounds have valuable pesticidal activity, particularly against arthropods and helminths. Pesticidal formulations containing the compounds of formula (I), their use in the control of pests and methods for their preparation are also disclosed.

  本发明提供了一类公式为##STR1##的取代双环辛烷化合物，其中R是C.sub.2-10非芳香族烃基，可选地被氰基，卤素，C.sub.1-4烷氧基，C.sub.1-4卤代烷氧基或S(O).sub.mR.sup.3取代; R.sup.1和R.sup.2分别是氢，卤素，C.sub.1-3脂肪基，可选地取代的S(O).sub.m,R.sup.4，或R.sup.1和R.sup.2及其所连接的碳原子形成可选地被卤素取代的C.sub.5-7环烷基或C.sub.1-3脂肪基或烷氧基; A-X是一个基团：(i) A'C.tbd.CX，其中A'是C.sub.3-6烷基，烯基或炔基或C.sub.3-10环烷基或环烯基，均可选地含有一到三个杂原子。(ii) BX，其中B是(CH.sub.2).sub.2O或(CH.sub.2).sub.2S(O).sub.n或C.sub.2-6脂肪链，可选地含有一或两个氧或硫原子和/或双键，并可选地进一步取代; X是氢，卤素，SiR.sup.5R.sup.6R.sup.7或SnR.sup.5R.sup.6R.sup.7或CR.sup.8R.sup.9R.sup.10; Y和Y.sup.1独立地是氧或S(O).sub.n'，Z是CH.sub.2S(O).sub.n"，前提是当A不含C.tbd.C片段时，X是CR.sup.8R.sup.9R.sup.10基团。这些化合物具有有价值的杀虫活性，特别是对节肢动物和蠕虫。还公开了含有公式(I)化合物的杀虫剂配方、它们在害虫控制中的使用以及它们的制备方法。
• US5116862A
  申请人：——

  公开号：US5116862A

  公开（公告）日：1992-05-26
• US5466710A
  申请人：——

  公开号：US5466710A

  公开（公告）日：1995-11-14
• 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.