dipropan-2-yl (4R,5R)-2-[(1R,2S)-1-methyl-2-phenylcyclopropyl]-1,3-dioxolane-4,5-dicarboxylate | 178941-27-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dipropan-2-yl (4R,5R)-2-[(1R,2S)-1-methyl-2-phenylcyclopropyl]-1,3-dioxolane-4,5-dicarboxylate
• CAS: 178941-27-0
• 化学式: C₂₁H₂₈O₆
• 分子量: 376.45
• InChiKey: RFLQRHUSKYJZPQ-BIZBXSGISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dipropan-2-yl (4R,5R)-2-[(1R,2S)-1-methyl-2-phenylcyclopropyl]-1,3-dioxolane-4,5-dicarboxylate 在 sodium tetrahydroborate 、 高氯酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 13.0h， 生成 (1R,2S)-E-1-hydroxymethyl-1-methyl-2-phenylcyclopropane
  参考文献：
  名称：

  Synthesis and stereostructure–activity relationship of a synthetic pyrethroid, 2-chloro-1-methyl-3-phenylcyclopropylmethyl-3-phenoxybenzyl ether

  摘要：

  Of the four diastereoisomers of 2-chloro-1-methyl-3-phenylcyclopropylmet 3-phenoxybenzyl ether 5, a new type of synthetic pyrethroid, which have been synthesized, only the (1R*,2S*,3S*)-isomer 5a showed significant insecticidal activity against the tobacco cutworm and the common mosquito. Two enantiomers (1R,2S,3S)-(-)-5a and (1S,2R,3R)-(+)-5a were prepared by the optical resolution process, and their absolute configurations were determined by chemical derivatization via predictable asymmetric cyclopropanation. Bioassay showed that the (1R,2S,3S)-(-)-5a was active, while (1S,2R,3R)-(+)-5a was not. The geometry around the asymmetric centre of the (1R,2S,3S)-enantiomer was correlated with that of representative pyrethroids which are both optically active and have insecticidal activity.

  DOI：

  10.1039/p19960001243
• 作为产物：
  描述：

  L-(+)-酒石酸二异丙酯 在 diethylzinc 、 (+)-10-camphorsulfonic acid 作用下， 以 正己烷 、 苯 为溶剂， 反应 3.0h， 生成 dipropan-2-yl (4R,5R)-2-[(1R,2S)-1-methyl-2-phenylcyclopropyl]-1,3-dioxolane-4,5-dicarboxylate
  参考文献：
  名称：

  Synthesis and stereostructure–activity relationship of a synthetic pyrethroid, 2-chloro-1-methyl-3-phenylcyclopropylmethyl-3-phenoxybenzyl ether

  摘要：

  Of the four diastereoisomers of 2-chloro-1-methyl-3-phenylcyclopropylmet 3-phenoxybenzyl ether 5, a new type of synthetic pyrethroid, which have been synthesized, only the (1R*,2S*,3S*)-isomer 5a showed significant insecticidal activity against the tobacco cutworm and the common mosquito. Two enantiomers (1R,2S,3S)-(-)-5a and (1S,2R,3R)-(+)-5a were prepared by the optical resolution process, and their absolute configurations were determined by chemical derivatization via predictable asymmetric cyclopropanation. Bioassay showed that the (1R,2S,3S)-(-)-5a was active, while (1S,2R,3R)-(+)-5a was not. The geometry around the asymmetric centre of the (1R,2S,3S)-enantiomer was correlated with that of representative pyrethroids which are both optically active and have insecticidal activity.

  DOI：

  10.1039/p19960001243