(-)-2-phenylapopinene | 124355-71-1

• 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: (-)-2-phenylapopinene
• 英文别名: (1R,5S)-6,6-dimethyl-2-phenylbicyclo[3.1.1]hept-2-ene
• CAS: 124355-71-1
• 化学式: C₁₅H₁₈
• 分子量: 198.308
• InChiKey: SYRDENIJTJYALZ-JSGCOSHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  (-)-2-phenylapopinene 在 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (+)-2-phenylapoisopinocampheol
  参考文献：
  名称：

  Synthesis and reactions of terpenyl diselenides functionalized with phenyl and naphthyl groups

  摘要：

  An efficient methodology for the synthesis of chiral terpenyl diselenides functionalized with phenyl and naphthyl groups has been developed. Using the reaction of sodium diselenide with terpenyl tosylates and chlorides, the corresponding diselenides derived from 8-phenyl menthol and isopinocampheol modified at the 10-position were obtained. Diselenides were transformed into electrophilic selenium reagents and tested in the asymmetric selenenylation of styrene. The effect of aryl groups on the enantioselectivity of the addition reaction was examined. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.02.004
• 作为产物：
  描述：

  beta-pinene 在 臭氧 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 (-)-2-phenylapopinene
  参考文献：
  名称：

  Synthesis and reactions of terpenyl diselenides functionalized with phenyl and naphthyl groups

  摘要：

  An efficient methodology for the synthesis of chiral terpenyl diselenides functionalized with phenyl and naphthyl groups has been developed. Using the reaction of sodium diselenide with terpenyl tosylates and chlorides, the corresponding diselenides derived from 8-phenyl menthol and isopinocampheol modified at the 10-position were obtained. Diselenides were transformed into electrophilic selenium reagents and tested in the asymmetric selenenylation of styrene. The effect of aryl groups on the enantioselectivity of the addition reaction was examined. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.02.004

文献信息

• Hydroboration. 85. Synthesis and hydroboration of (-)-2-phenylapopinene. Comparison of mono(2-phenylapoisopinocampheyl)borane with its 2-methyl and 2-ethyl analogs for the chiral hydroboration of representative alkenes
  作者：Herbert C. Brown、Steven A. Weissman、P. T. Perumal、U. P. Dhokte

  DOI：10.1021/jo00291a021

  日期：1990.2
• Hydroboration of Terpenes. 11. Convenient Method for Upgrading 2-Organylapopinenes to High Optical Purity by Reaction of 2-Organylapoisopinocampheylboranes with Suitable Dienes Followed by Displacement with Acetaldehyde
  作者：Herbert C. Brown、Ulhas P. Dhokte

  DOI：10.1021/jo00097a065

  日期：1994.9
• New chiral auxiliaries derived from β -pinene: Their use in the asymmetric reduction of β-keto-esters
  作者：Mário Luiz Vasconcellos、Jean d'Angelo、Didier Desmaele、Paulo R.R. Costa、Dominique Potin

  DOI：10.1016/s0957-4166(00)82117-5

  日期：1991.1

  3-Ketobutyrates 6, derived from chiral auxiliary alcohols 5 - themselves efficiently prepared from beta-pinene 4 - were reduced with zinc borohydride, giving 3-hydroxybutyrates 7 with 2-70 % de, depending on the nature of aryl group in alcohols 5.
• BROWN, HERBERT C.;WEISSMAN, STEVEN A.;PERUMAL, P. T.;DHOKTE, U. P., J. ORG. CHEM., 55,(1990) N, C. 1217-1223
  作者：BROWN, HERBERT C.、WEISSMAN, STEVEN A.、PERUMAL, P. T.、DHOKTE, U. P.

  DOI：——

  日期：——