2,2-Dichlor-1-methyl-3c-phenyl-1r-cyclopropanmethanol-tetrahydro-2-pyranylether | 77301-64-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 2,2-Dichlor-1-methyl-3c-phenyl-1r-cyclopropanmethanol-tetrahydro-2-pyranylether
• 英文别名: 2-[[(1S,3S)-2,2-dichloro-1-methyl-3-phenylcyclopropyl]methoxy]oxane
• CAS: 77301-64-5；77341-59-4；100163-46-0；100163-47-1
• 化学式: C₁₆H₂₀Cl₂O₂
• 分子量: 315.24
• InChiKey: BMUYZPSNJMYYKU-NOYMGPGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2-Dichlor-1-methyl-3c-phenyl-1r-cyclopropanmethanol-tetrahydro-2-pyranylether 在 偶氮二异丁腈 甲醇 、 potassium fluoride 、 三正丁基氢锡 、 4-甲基苯磺酸吡啶 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 (1R*,2R*,3R*)-2-Chloro-1-methyl-3-phenylcyclopropylmethyl 3-phenoxybenzyl ether
  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：

  (Z)-3-phenyl-2-methyl-2-propenol 在 苄基三乙基氯化铵 、 (+)-10-camphorsulfonic acid sodium hydroxide 作用下， 以 乙醚 为溶剂， 反应 12.0h， 生成 2,2-Dichlor-1-methyl-3c-phenyl-1r-cyclopropanmethanol-tetrahydro-2-pyranylether
  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

文献信息

• Huelskaemper, Ludwig; Weyerstahl, Peter, Chemische Berichte, 1981, vol. 114, # 2, p. 746 - 756
  作者：Huelskaemper, Ludwig、Weyerstahl, Peter

  DOI：——

  日期：——
• Synthesis and stereostructure–activity relationship of a synthetic pyrethroid, 2-chloro-1-methyl-3-phenylcyclopropylmethyl-3-phenoxybenzyl ether
  作者：Yoshinori Nishii、Ken-ichi Wakimura、Toru Tsuchiya、Shogo Nakamura、Yoo Tanabe

  DOI：10.1039/p19960001243

  日期：——

  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.