methyl (2R,3S)-3-((R)-4,8-dimethylnon-7-en-1-yl)-3-methyloxirane-2-carboxylate | 1352303-88-8

• 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: methyl (2R,3S)-3-((R)-4,8-dimethylnon-7-en-1-yl)-3-methyloxirane-2-carboxylate
• CAS: 1352303-88-8
• 化学式: C₁₆H₂₈O₃
• 分子量: 268.397
• InChiKey: FHOAXADPAFMMKS-DZKIICNBSA-N

物化性质

• 沸点：
  317.5±17.0 °C(Predicted)
• 密度：
  0.957±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  19.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  38.83
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl (2R,3S)-3-((R)-4,8-dimethylnon-7-en-1-yl)-3-methyloxirane-2-carboxylate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以97%的产率得到methyl (2R,3S)-3-[(4R)-6-(3,3-dimethyloxiran-2-yl)-4-methylhexyl]-3-methyloxirane-2-carboxylate
  参考文献：
  名称：

  Structure–activity relationship of novel juvenile hormone, JHSB3, isolated from the stink bug, Plautia stali

  摘要：

  The structure-activity relationship of JHSB(3) isolated from the pentatomid bug. Plautia stali, was studied. Various synthetic analogs were synthesized and subjected to the juvenilizing activity tests using the last instar nymphs of P. stali. These studies indicated that the coexistence of the ester carbonyl group, two epoxides at C2,3 and C10,11 were proved to be crucial for the potent juvenilizing activity. Among the tested analogs, we found highly potent analogs in which the C6,7 double bond of JHSB3 was saturated (0.1 mu g/insect). The methoxy analogs in which the epoxide moiety at C10,11 was substituted with a methoxy group exerted a moderate juvenilizing activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.080
• 作为产物：
  描述：

  (2R,3S)-3-((R)-4,8-dimethylnon-7-en-1-yl)-3-methyloxirane-2-carbaldehyde 在 sodium chlorite 、 sodium dihydrogenphosphate dihydrate 、 2-甲基-2-丁烯 作用下， 以 乙醚 、 水 、 叔丁醇 为溶剂， 反应 2.0h， 生成 methyl (2R,3S)-3-((R)-4,8-dimethylnon-7-en-1-yl)-3-methyloxirane-2-carboxylate
  参考文献：
  名称：

  Structure–activity relationship of novel juvenile hormone, JHSB3, isolated from the stink bug, Plautia stali

  摘要：

  The structure-activity relationship of JHSB(3) isolated from the pentatomid bug. Plautia stali, was studied. Various synthetic analogs were synthesized and subjected to the juvenilizing activity tests using the last instar nymphs of P. stali. These studies indicated that the coexistence of the ester carbonyl group, two epoxides at C2,3 and C10,11 were proved to be crucial for the potent juvenilizing activity. Among the tested analogs, we found highly potent analogs in which the C6,7 double bond of JHSB3 was saturated (0.1 mu g/insect). The methoxy analogs in which the epoxide moiety at C10,11 was substituted with a methoxy group exerted a moderate juvenilizing activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.080