(4S)-4-异丙基-1-甲基-7-氧杂双环[4.1.0]庚烷 | 579473-51-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 中文名称: (4S)-4-异丙基-1-甲基-7-氧杂双环[4.1.0]庚烷
• 英文名称: (-)-carvomethene epoxide
• 英文别名: epoxy-(S)-carvomenthane；(-)(1Ξ,2Ξ,4S)-1,2-epoxy-p-menthane；(-)(1Ξ,2Ξ,4S)-1,2-Epoxy-p-menthan；1,2-Epoxy-p-menthan；(4S)-1-methyl-4-propan-2-yl-7-oxabicyclo[4.1.0]heptane
• CAS: 579473-51-1
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: WSHVHJSDSVPPIV-IDKOKCKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4S)-4-异丙基-1-甲基-7-氧杂双环[4.1.0]庚烷 在 哌啶 、 sodium periodate 、 硫酸 、 二异丁基氢化铝 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 水 、 苯 为溶剂， 反应 111.0h， 生成 (-)-1-methyl-2-(hydroxymethyl)-3(R)-isopropylcyclopentene
  参考文献：
  名称：

  A convergent synthesis of triquinane sesterterpenes. Enantioselective synthesis of (-)-retigeranic acid A

  摘要：

  DOI：

  10.1021/ja00225a036
• 作为产物：
  描述：

  (S)-(-)-柠檬烯 在 Raney nickel W₄ 氢气 、 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 生成 (4S)-4-异丙基-1-甲基-7-氧杂双环[4.1.0]庚烷
  参考文献：
  名称：

  Determination of the Absolute Configuration of Quercivorol, (1S,4R)-p-Menth-2-en-1-ol, an Aggregation Pheromone of the Ambrosia BeetlePlatypus quercivorus(Coleoptera: Platypodidae)

  摘要：

  由(S)-和(R)-亚甲烯烃合成了一对反式对薄荷素-2-烯-1-醇（鸭嘴兽的一种聚集信息素）的对映体。通过使用手性色谱柱进行气相色谱分析，该昆虫的聚集信息素与由(S)-柠檬烯合成的(1S,4R)-p-menth-2-烯-1-醇的保留时间相吻合，从而确定了聚集信息素的绝对构型为(1S,4R)。

  DOI：

  10.1271/bbb.60211

文献信息

• Syntheses of the Optically Active Terpene Hydroxyphenylselenides
  作者：Jacek Ścianowski、Mirosław Wełniak

  DOI：10.1080/10426500902947682

  日期：2009.6.23

  The optically active hydroxyphenylselenides derived from the p-menthane, carane, and pinane systems have been obtained. Two methods of hydroxyphenylselenides synthesis have been compared. The first method is based on the reaction of alkenes with N-(phenylseleno)succinimide in the presence of water, and the second from epoxides as a result of the reaction with sodium benzeneselenolate. The influence

  已经获得了衍生自对薄荷烷、卡拉烷和蒎烷体系的旋光羟基苯硒化物。已经比较了羟苯基硒化物的两种合成方法。第一种方法基于烯烃与 N-(苯基硒基)琥珀酰亚胺在水存在下的反应，第二种方法是与苯硒酸钠反应产生的环氧化物。已经证明了基材结构对所得产品组成的影响。
• FRAGRANCES WITH NOTE OF LILY OF THE VALLEY
  申请人：Singer Emilie

  公开号：US20130090390A1

  公开（公告）日：2013-04-11

  A compound of formula (I) is described and use thereof as fragrance, especially as lily-of-the-valley fragrance and/or as an agent for increasing the substantivity and/or the retention of a fragrance preparation and/or as a fixative.

  描述了化学式（I）的化合物及其用途，特别是作为百合花香气，和/或作为增加香气制剂的持久性和/或保留性的剂，和/或作为固定剂。
• Ring-opening of enantiomerically pure oxa-containing heterocycles with phosphorus nucleophiles
  作者：Héctor Fernández-Pérez、Pablo Etayo、José Luis Núñez-Rico、Bugga Balakrishna、Anton Vidal-Ferran

  DOI：10.1039/c4ra10432c

  日期：——

  Various oxa-containing heterocycles (i.e. enantiopure epoxide- and oxetane-based substrates) were subjected to ring-opening with phosphorus nucleophiles. The ring-opening reactions proceeded smoothly and the resulting 1,2-, and 1,3-phosphino alcohols were efficiently isolated as stable borane complexes. These derivatives arise from regio- and stereocontrolled syntheses based on ring-opening processes of oxa-containing heterocycles. The regio- and stereochemistry of the resulting chiral products were unequivocally confirmed in many cases via single-crystal X-ray diffraction analysis.

  各种含氧杂环（即对映纯环氧化物和氧杂环丁烷基底物）与磷亲核剂进行了开环反应。开环反应顺利进行，生成的 1,2-和 1,3-膦醇以稳定的硼烷络合物形式被有效地分离出来。这些衍生物是基于含氧杂环的开环过程进行区域和立体控制合成而得到的。在许多情况下，通过单晶 X 射线衍射分析，所得到的手性产物的区域和立体化学结构都得到了明确的证实。
• Synthesis of (1S,4R)-4-isopropyl-1-methyl-2-cyclohexen-1-ol, the aggregation pheromone of the ambrosia beetle Platypus quercivorus, its racemate, (1R,4R)- and (1S,4S)-isomers
  作者：Kenji Mori

  DOI：10.1016/j.tetasy.2006.07.030

  日期：2006.8

  (S)-Perillyl alcohol was converted to (R)-cryptone (91.5-93% ee) in six steps, which was then treated with methyllithium to give (1S,4R)-4-isopropyl-1-methyl-2-cyclohexen-1-ol, the aggregation pheromone of the ambrosia beetle Platypus quercivorus. The racemic pheromone was also prepared by methylation of (+/-)-cryptone. Both (1R,4R)- and (1S,4S)-isomers (98% ee) of the pheromone were synthesized from the enantiomers of dihydrolimonene oxide. (c) 2006 Elsevier Ltd. All rights reserved.
• CrIII(salen) catalysed asymmetric ring opening of monocyclic terpene-epoxides
  作者：Bart M.L Dioos、Pierre A Jacobs

  DOI：10.1016/s0040-4039(03)01052-9

  日期：2003.6

  The racemic Cr-III(salen) complex was found to be an efficient catalyst for the asymmetric ring opening (ARO) with TMSN3 of cyclic 1,2-epoxy-terpenes bearing C-4-substituents. (C) 2003 Elsevier Science Ltd. All rights reserved.