(-)-α-phellandrene | 56169-11-0

• 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: (-)-α-phellandrene
• 英文别名: (S)-p-mentha-1,5,8-triene；(-)(S)-p-menthatriene-(1.5.8(9))；(-)(S)-p-Menthatrien-(1.5.8(9))；(5S)-2-Methyl-5-(1-methylethenyl)-1,3-cyclohexadiene；(5S)-2-methyl-5-prop-1-en-2-ylcyclohexa-1,3-diene
• CAS: 56169-11-0
• 化学式: C₁₀H₁₄
• 分子量: 134.221
• InChiKey: NJLNIOKPXKKALD-SNVBAGLBSA-N

物化性质

• 沸点：
  179.4±20.0 °C(Predicted)
• 密度：
  0.857±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (-)-α-phellandrene 在 sodium hydroxide 、 9-borabicyclo[3.3.1]nonane dimer 、 双氧水 作用下， 生成 (4S)-p-mentha-1,5-dien-9-ol
  参考文献：
  名称：

  Enantiocontrolled Formal Total Synthesis of Paeonilactone A and B from (S)-(+)-Carvone.

  摘要：

  A synthesis of enantiomerically pure lactone 11a from commercially available (S)-(+)-carvone has been developed. The synthesis constitutes a formal synthesis of paeonilactone A and B and involves a stereoselective palladium-catalyzed 1,4-oxylactonization of a conjugated diene to introduce two of the oxygen substituents required for the target.

  DOI：

  10.3891/acta.chem.scand.52-0524
• 作为产物：
  描述：

  (S)-carvone tosylhydrazone 在 甲基锂 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以87%的产率得到(-)-α-phellandrene
  参考文献：
  名称：

  Enantiocontrolled Formal Total Synthesis of Paeonilactone A and B from (S)-(+)-Carvone.

  摘要：

  A synthesis of enantiomerically pure lactone 11a from commercially available (S)-(+)-carvone has been developed. The synthesis constitutes a formal synthesis of paeonilactone A and B and involves a stereoselective palladium-catalyzed 1,4-oxylactonization of a conjugated diene to introduce two of the oxygen substituents required for the target.

  DOI：

  10.3891/acta.chem.scand.52-0524

文献信息

• Chemoenzymatic preparation of the p-menth-1,5-dien-9-ol stereoisomers and their use in the enantiospecific synthesis of natural p-menthane monoterpenes
  作者：Stefano Serra、Igor Nobile

  DOI：10.1016/j.tetasy.2011.07.014

  日期：2011.7

  alcohols gave the isomeric forms of the terpenes dill and epi-dill ether, which were hydrogenated diastereoselectively to the corresponding (1R)- or (1S)-derivatives depending on the catalyst used. The oxidation of the latter ethers turned out to be stereoselective, affording either the corresponding p-menthan-9-oic lactone or the keto-acid derivatives depending on the starting isomer used.

  对p -menth-1,5-dien-9-ol的异构体形式的制备和合成研究进行了报道。后者的醇是从香芹酮的容易获得的对映异构体中以高对映异构体纯度制备的。因此，基于脂肪酶介导的乙酰化作用的化学酶法可以分离其非对映异构形式。此外，通过对其3，5-二硝基苯甲酰基衍生物进行分步结晶，可以提高所获得的手性结构单元的纯度。还描述了许多合成应用。异构纯二烯醇的立体定向环化反应得到萜烯莳萝和表-莳萝醚的异构体形式，它们经非对映选择性氢化成相应的（1 R）或（1 S）-衍生物，具体取决于所使用的催化剂。后来的醚的氧化被证明是立体选择性的，根据所用的起始异构体，得到相应的对-menthan-9-oo内酯或酮酸衍生物。
• Lipnicka,U.; Chabudzinski,Z., Roczniki Chemii, 1975, vol. 49, p. 307 - 314
  作者：Lipnicka,U.、Chabudzinski,Z.

  DOI：——

  日期：——
• 212. Reduction by dissolving metals. Part II
  作者：Arthur J. Birch

  DOI：10.1039/jr9450000809

  日期：——
• Alder; Schumacher, Chemische Berichte, 1956, vol. 89, p. 2485,2493
  作者：Alder、Schumacher

  DOI：——

  日期：——
• Enantiocontrolled Formal Total Synthesis of Paeonilactone A and B from (S)-(+)-Carvone.
  作者：Magnus Rönn、Pher G. Andersson、Jan-E. Bäckvall、Olle Matsson、Jadwiga Trocha-Grimshaw、Ole Hammerich、Inger Søtofte、Bengt Långström

  DOI：10.3891/acta.chem.scand.52-0524

  日期：——

  A synthesis of enantiomerically pure lactone 11a from commercially available (S)-(+)-carvone has been developed. The synthesis constitutes a formal synthesis of paeonilactone A and B and involves a stereoselective palladium-catalyzed 1,4-oxylactonization of a conjugated diene to introduce two of the oxygen substituents required for the target.