(1S,5R)-5-[(2S)-6-methylhept-5-en-2-yl]bicyclo[3.1.0]hexan-2-one | 1309460-43-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,5R)-5-[(2S)-6-methylhept-5-en-2-yl]bicyclo[3.1.0]hexan-2-one
• CAS: 1309460-43-2
• 化学式: C₁₄H₂₂O
• 分子量: 206.328
• InChiKey: SUIQTVSDXGWHFH-OUCADQQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1S,5R)-5-[(2S)-6-methylhept-5-en-2-yl]bicyclo[3.1.0]hexan-2-one 在 iron(III)-acetylacetonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 正己烷 为溶剂， 生成 (-)-(2R,6R,7S)-7-epi-sesquithujene
  参考文献：
  名称：

  Absolute Configuration of 7-epi-Sesquithujene

  摘要：

  7-epi-Sesquithujene (1) is a bicyclic sesquiterpene isolated from phoebe oil, an essential oil of the Brazilian walnut tree, Phoebe porosa. It is also produced by stressed ash trees and has been shown to elicit strong electrophysiological responses on emerald ash borer, Agrilus planipennis, antennae. In the course of the development of a synthetic 7-epi-sesquithujene lure for field testing against the emerald ash borer, we found that the absolute configuration of this compound had not been determined. We isolated >95% pure 7-epi-sesquithujene from phoebe oil via successive fractionation and conventional and argentation (HPLC) chromatographies. The specific optical rotation of this compound matched that of a synthetic product of known configuration. We also synthesized two other stereoisomers of sesquithujene and developed a chiral GC method to separate all four. Based on the specific rotation, stereoselective syntheses, and chiral GC analyses, 7-epi-sesquithujene present in phoebe oil and white ash was found to have the 2S,6S,7R absolute configuration.

  DOI：

  10.1021/np200098z
• 作为产物：
  描述：

  2-methyl-6-(4'-oxobicyclo[3.1.0]hexyl)hept-2-ene 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 碘苯二乙酸 、 L-Selectride 作用下， 以 四氢呋喃 、 二氯甲烷 、 正戊烷 为溶剂， 反应 4.0h， 生成 (1S,5R)-5-[(2S)-6-methylhept-5-en-2-yl]bicyclo[3.1.0]hexan-2-one
  参考文献：
  名称：

  Absolute Configuration of 7-epi-Sesquithujene

  摘要：

  7-epi-Sesquithujene (1) is a bicyclic sesquiterpene isolated from phoebe oil, an essential oil of the Brazilian walnut tree, Phoebe porosa. It is also produced by stressed ash trees and has been shown to elicit strong electrophysiological responses on emerald ash borer, Agrilus planipennis, antennae. In the course of the development of a synthetic 7-epi-sesquithujene lure for field testing against the emerald ash borer, we found that the absolute configuration of this compound had not been determined. We isolated >95% pure 7-epi-sesquithujene from phoebe oil via successive fractionation and conventional and argentation (HPLC) chromatographies. The specific optical rotation of this compound matched that of a synthetic product of known configuration. We also synthesized two other stereoisomers of sesquithujene and developed a chiral GC method to separate all four. Based on the specific rotation, stereoselective syntheses, and chiral GC analyses, 7-epi-sesquithujene present in phoebe oil and white ash was found to have the 2S,6S,7R absolute configuration.

  DOI：

  10.1021/np200098z

文献信息

• Absolute Configuration of 7-<i>epi</i>-Sesquithujene
  作者：Ashot Khrimian、Allard A. Cossé、Damon J. Crook

  DOI：10.1021/np200098z

  日期：2011.6.24

  7-epi-Sesquithujene (1) is a bicyclic sesquiterpene isolated from phoebe oil, an essential oil of the Brazilian walnut tree, Phoebe porosa. It is also produced by stressed ash trees and has been shown to elicit strong electrophysiological responses on emerald ash borer, Agrilus planipennis, antennae. In the course of the development of a synthetic 7-epi-sesquithujene lure for field testing against the emerald ash borer, we found that the absolute configuration of this compound had not been determined. We isolated >95% pure 7-epi-sesquithujene from phoebe oil via successive fractionation and conventional and argentation (HPLC) chromatographies. The specific optical rotation of this compound matched that of a synthetic product of known configuration. We also synthesized two other stereoisomers of sesquithujene and developed a chiral GC method to separate all four. Based on the specific rotation, stereoselective syntheses, and chiral GC analyses, 7-epi-sesquithujene present in phoebe oil and white ash was found to have the 2S,6S,7R absolute configuration.