2-methyl-6-(4'-oxobicyclo[3.1.0]hexyl)hept-2-ene | 943147-18-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methyl-6-(4'-oxobicyclo[3.1.0]hexyl)hept-2-ene
• 英文别名: 5-(6-methylhept-5-en-2-yl)bicyclo[3.1.0]hexan-2-one；5-[(2S)-6-methylhept-5-en-2-yl]bicyclo[3.1.0]hexan-2-one
• CAS: 943147-18-0
• 化学式: C₁₄H₂₂O
• 分子量: 206.328
• InChiKey: SUIQTVSDXGWHFH-DCBWTQNWSA-N

物化性质

• 沸点：
  142-146 °C(Press: 5 Torr)
• 密度：
  0.997±0.06 g/cm3(Predicted)

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：

  2-methyl-6-(4'-oxobicyclo[3.1.0]hexyl)hept-2-ene 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 iron(III)-acetylacetonate 、 碘苯二乙酸 、 L-Selectride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 正己烷 、 二氯甲烷 、 正戊烷 为溶剂， 反应 3.0h， 生成 (+)-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：

  (S)-1-diazo-6,10-dimethyl-5-methylene-9-undecen-2-one 在 铜 、 copper(II) sulfate 作用下， 以 环己烷 为溶剂， 反应 1.5h， 以43%的产率得到2-methyl-6-(4'-oxobicyclo[3.1.0]hexyl)hept-2-ene
  参考文献：
  名称：

  旨在阐明雄性臭虫Erysarcoris lewisi产生的聚集信息素2-甲基-6-（4'-亚甲基双环[3.1.0]己基）庚-2-烯-1-醇的立体结构的合成研究

  摘要：

  臭臭虫Erysarcoris lewisi Distant的雄性产生的聚集信息素被证明是（2 Z，6 R）-2-甲基-6-（4'-亚甲基双环[3.1.0]己基）庚烷的两个非对映异构体之一通过合成和生物测定（2 E，6 R）-，（2 E，6 S）-，（2 Z，6 R）-和（2 Z，6 S）-异构体来生成-2-en-1-ol 。这些是由香茅醛的对映异构体合成的，方法是将分子内的α-酮卡宾加成双键，并使用E-选择性或Z甲酰基的选择性烯烃化是关键步骤。开发了一种可靠的方法来制备2-（二-邻甲苯基膦酰基膦酸酯）丙酸乙酯，这是Ando的Z选择性烯化试剂。

  DOI：

  10.1016/j.tetasy.2007.03.019

文献信息

• Juniperanol: First total synthesis and evaluation in Type 2 Diabetes disease
  作者：A. Carrër、S. Turban、N. Provost、A. Caliez、G. Lamarche、G. Zanirato、M. Beucher、C. Pean、O. Mirguet、F. Perron-Sierra、V. Michelet

  DOI：10.1016/j.bioorg.2019.103243

  日期：2019.11

  The first total synthesis of juniperanol, the tricyclic sesquiterpenoid enantiomer of α-cedrol is described. The synthesis relies on stereoselective gold-catalyzed Ohloff-type propargylic ester rearrangement performed on a 10 g scale, and a carbocationic cascade in the presence of acetyl methanesulfonate. The ability of juniperanol to interfere in glucose processes in different cell types is described

  描述了杜仲醇的首次全合成，即α-西多洛尔的三环倍半萜类对映体。该合成依赖于在10 g规模上进行的立体选择性金催化的Ohloff型炔丙基酯重排，以及在乙酰基甲磺酸盐存在下的碳阳离子级联反应。描述了杜松醇干扰不同细胞类型的葡萄糖过程的能力。
• Synthetic studies aimed at the elucidation of the stereostructure of the aggregation pheromone, 2-methyl-6-(4′-methylenebicyclo[3.1.0]hexyl)hept-2-en-1-ol, produced by the male stink bug Erysarcoris lewisi
  作者：Kenji Mori

  DOI：10.1016/j.tetasy.2007.03.019

  日期：2007.4

  The male-produced aggregation pheromone of the stink bug Erysarcoris lewisi Distant was shown to be one of the two diastereomers of (2Z,6R)-2-methyl-6-(4′-methylenebicyclo[3.1.0]hexyl)hept-2-en-1-ol by synthesizing and bioassaying (2E,6R)-, (2E,6S)-, (2Z,6R)-, and (2Z,6S)-isomers. These were synthesized from the enantiomers of citronellal by employing an intramolecular α-ketocarbene addition to a double

  臭臭虫Erysarcoris lewisi Distant的雄性产生的聚集信息素被证明是（2 Z，6 R）-2-甲基-6-（4'-亚甲基双环[3.1.0]己基）庚烷的两个非对映异构体之一通过合成和生物测定（2 E，6 R）-，（2 E，6 S）-，（2 Z，6 R）-和（2 Z，6 S）-异构体来生成-2-en-1-ol 。这些是由香茅醛的对映异构体合成的，方法是将分子内的α-酮卡宾加成双键，并使用E-选择性或Z甲酰基的选择性烯烃化是关键步骤。开发了一种可靠的方法来制备2-（二-邻甲苯基膦酰基膦酸酯）丙酸乙酯，这是Ando的Z选择性烯化试剂。
• 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.