(1R,2R,5R)-2,6,6-Trimethylbicyclo<3.1.1>hept-3-en-2-ol | 149404-73-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,2R,5R)-2,6,6-Trimethylbicyclo<3.1.1>hept-3-en-2-ol
• 英文别名: (2R)-(+)-trans-Pin-3-en-2-ol；cis-2-Hydroxypin-3(4)-ene；trans-2-Hydroxypin-3(4)-ene；(2S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol；(1R,2R)-pin-3-en-2-ol；(1R,2R,5R)-2,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol
• CAS: 149404-73-9
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: QBKKSIMANOEXOI-QXFUBDJGSA-N

物化性质

• 沸点：
  204.9±9.0 °C(Predicted)
• 密度：
  0.999±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1R,2R,5R)-2,6,6-Trimethylbicyclo<3.1.1>hept-3-en-2-ol 在 Celite 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以79%的产率得到马鞭草烯醇
  参考文献：
  名称：

  Efficient synthesis of (1S,5S)-4-alkyl-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-ones from (1R,5S)-(+)-nopinone and preparation of some chiral building blocks suitable for the asymmetric synthesis

  摘要：

  A general and convenient transformation of (1R,5S)-(+)-nopinone (1) into (1S,5S)-4-alkyl-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-ones, i.e., (-)-verbenone (6a) as the simplest compound and its C(4)-alkyl homologs 6b-f, via (+)-apoverbenone (7) is developed and applied, starting with 6a,e, to the syntheses of (4R,5R)-1-acetoxy-4-isopropenyl-5-methyl-5-vinyl-1-cyclohexene (12a) and (4R,5S)- and (4R,5R)-1-acetoxy-5-(3-butenyl)-4-isopropenyl-5-methyl-1-cyclohexene (12b and 12c), in connection with a search for chiral building blocks suitable for the asymmetric synthesis. Preparation of 12a indicates the formal synthesis of the elemanoid sesquiterpenes (-)-beta-elemenone and (-)-eleman-8beta,12-olide.

  DOI：

  10.1021/jo00067a026
• 作为产物：
  描述：

  (-)-α-蒎烯 在 air 作用下， 生成 (1R,2R,5R)-2,6,6-Trimethylbicyclo<3.1.1>hept-3-en-2-ol
  参考文献：
  名称：

  Production of oxygenated terpenes from alpha-pinene

  摘要：

  公开号：

  US02911442A1

文献信息

• Highly Potent Activity of (1<i>R</i>,2<i>R</i>,6<i>S</i>)-3-Methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol in Animal Models of Parkinson’s Disease
  作者：Oleg V. Ardashov、Alla V. Pavlova、Irina V. Il’ina、Ekaterina A. Morozova、Dina V. Korchagina、Elena V. Karpova、Konstantin P. Volcho、Tat’yana G. Tolstikova、Nariman F. Salakhutdinov

  DOI：10.1021/jm2001579

  日期：2011.6.9

  (1R,2R,6S)-3-Methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol 1 possesses potent antiparkinsonian activity in both MPTP and haloperidol animal models. The use of compound 1 resulted in nearly full recovery of the locomotor and exploratory activities and was as effective as the comparator agent (levodopa). All eight stereoisomers of compound 1 have been synthesized and the influence of the absolute configuration on the antiparkinsonian activity of compound 1 was shown.

  (1R,2R,6S)-3-甲基-6-(丙-1-烯-2-基)环己-3-烯-1,2-二醇 1 在 MPTP 和氟哌啶醇动物模型中均表现出强效的抗帕金森症活性。使用化合物 1 能使运动和探索活动几乎完全恢复，其效果与对照药物（左旋多巴）相当。化合物 1 的八个立体异构体均已被合成，且其绝对构型对抗帕金森症活性的影响也已得到验证。
• Die absolute konfiguration des linalools durch verknüpfung mit dem pinansystem
  作者：G. Ohloff、E. Klein

  DOI：10.1016/0040-4020(62)80021-0

  日期：1962.1

  A new independent proof of the absolute configuration of linalool is given by its pyrolytical formation from the diastereomeric pinane-2-ols.

  芳樟醇的绝对构型的新的独立证明是由非对映体pin烷-2-醇的热解形成提供的。
• Preparation of verbenone
  申请人：GLIDDEN CO

  公开号：US02767215A1

  公开（公告）日：1956-10-16
• The Reaction of Singlet Oxygen with ?- and ?-Pinenes
  作者：Charles W. Jefford、Andr� F. Boschung、Robert M. Moriarty、Christian G. Rimbault、Mostyn H. Laffer

  DOI：10.1002/hlca.19730560748

  日期：1973.11.7

  AbstractThe reaction of photogenerated singlet oxygen with α‐ and β‐pinenes has been carefully re‐examined. α‐Pinene almost exclusively (99.3% yield) furnishes trans‐3‐hydroperoxy‐pin2(10)‐ene. However, detectable amounts of the three other possible products are also found, viz., cis‐3‐hydroperoxypin‐2 (10)‐ene (˜0.8%), and cis‐ and trans‐2‐hydroperoxypin‐3 (4)‐ene (˜0.04%). β‐Pinene gives 99.9% of 10‐hydroperoxypin‐2 (3)‐ene and a trace (˜0.01%) of norpinan‐2‐one. Rates of reaction and product composition are treated by modal analysis and reflect the operation of steric and stereoelectronic factors in a reactant‐like transition state.
• Efficient synthesis of (1S,5S)-4-alkyl-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-ones from (1R,5S)-(+)-nopinone and preparation of some chiral building blocks suitable for the asymmetric synthesis
  作者：Masataka Watanabe、Bahlul Z. Awen、Michiharu Kato

  DOI：10.1021/jo00067a026

  日期：1993.7

  A general and convenient transformation of (1R,5S)-(+)-nopinone (1) into (1S,5S)-4-alkyl-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-ones, i.e., (-)-verbenone (6a) as the simplest compound and its C(4)-alkyl homologs 6b-f, via (+)-apoverbenone (7) is developed and applied, starting with 6a,e, to the syntheses of (4R,5R)-1-acetoxy-4-isopropenyl-5-methyl-5-vinyl-1-cyclohexene (12a) and (4R,5S)- and (4R,5R)-1-acetoxy-5-(3-butenyl)-4-isopropenyl-5-methyl-1-cyclohexene (12b and 12c), in connection with a search for chiral building blocks suitable for the asymmetric synthesis. Preparation of 12a indicates the formal synthesis of the elemanoid sesquiterpenes (-)-beta-elemenone and (-)-eleman-8beta,12-olide.