2-cis-4-trans-S-methoprene | 134678-54-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-cis-4-trans-S-methoprene
• 英文别名: (2Z,4E,7S)-1-Methylethyl 11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate；propan-2-yl (2Z,4E,7S)-11-methoxy-3,7,11-trimethyldodeca-2,4-dienoate
• CAS: 134678-54-9
• 化学式: C₁₉H₃₄O₃
• 分子量: 310.477
• InChiKey: NFGXHKASABOEEW-WTPASGINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  S-(+)-7-methoxy-3,7-dimethyl-1-octene 在 氢氧化钾 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 5.5h， 生成 2-cis-4-trans-S-methoprene
  参考文献：
  名称：

  Terpenes in organic synthesis 13. Synthesis of s-(+)-methoprene from (+)-?-citronellene

  摘要：

  S-(+)-Methoprene (I) was synthesized from (+)-beta-citronellene (III) with an optical purity of about 50%. The optical purity of the key intermediate, S-(-)-7-methoxy-3,7-dimethyl-1-octanol (IV), can be increased by fractional crystallization of the optically active acid phthalate salt (VI) followed by hydrolytic regeneration of alcohol (IV). The yield of (I) at the final synthetic stage can be increased by use of interphase catalysis. S-(+)-Methoprene has a higher morphogenetic activity than the racemic form.

  DOI：

  10.1007/bf00958564

文献信息

• Photoproducts and Metabolites of a Common Insect Growth Regulator Produce Developmental Deformities in <i>Xenopus</i>
  作者：James J. La Clair、John A. Bantle、James Dumont

  DOI：10.1021/es971024h

  日期：1998.5.1

  In the past decade, numerous sights across North America have been found which contain abnormal levels of deformed amphibians. This deformation was not limited to species, geography, or climate and spanned a wide range of phenotypes. This report begins to explain these findings by examining the effects of pesticide degradation in early amphibian development through directly exposing Xenopus laevis embryos to trace levels of synthetically prepared degradates. This method specifically determines the risk posed by each individual chemical resulting from the natural fate of the host pesticide. Through this approach, we find that while the common insect growth regulator, S-methoprene, poses minimal developmental determent, products of its reaction with sunlight, water, and microorganisms dramatically interfere with normal amphibian development. The addition of 1 mu L/L of several of S-methoprene's degradates to the environment of developing embryos resulted in juveniles with deformation similar to that found naturally. Current developmental assessments examine only the risk posed by host pesticides. This study now suggest that the simple examination of the these materials is not sufficient, but now forward the need for critically examining the temporal relation between both development and chemical degradation.
• Terpenes in organic synthesis 13. Synthesis of s-(+)-methoprene from (+)-?-citronellene
  作者：�. P. Serebryakov、G. M. Zhdankina、G. V. Kryshtal'、M. V. Mavrov、Nguen Kong Khao

  DOI：10.1007/bf00958564

  日期：1991.4

  S-(+)-Methoprene (I) was synthesized from (+)-beta-citronellene (III) with an optical purity of about 50%. The optical purity of the key intermediate, S-(-)-7-methoxy-3,7-dimethyl-1-octanol (IV), can be increased by fractional crystallization of the optically active acid phthalate salt (VI) followed by hydrolytic regeneration of alcohol (IV). The yield of (I) at the final synthetic stage can be increased by use of interphase catalysis. S-(+)-Methoprene has a higher morphogenetic activity than the racemic form.