(3R,4aR,5S,8aR)-3',3',4a,5-tetramethylspiro[4,5,6,7,8,8a-hexahydro-1H-naphthalene-3,2'-oxirane]-2-one | 51795-17-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4aR,5S,8aR)-3',3',4a,5-tetramethylspiro[4,5,6,7,8,8a-hexahydro-1H-naphthalene-3,2'-oxirane]-2-one
• CAS: 51795-17-6
• 化学式: C₁₅H₂₄O₂
• 分子量: 236.354
• InChiKey: LOCNHDXIIIFRKG-DRABBMOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  29.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R,4aR,5S,8aR)-3',3',4a,5-tetramethylspiro[4,5,6,7,8,8a-hexahydro-1H-naphthalene-3,2'-oxirane]-2-one 在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 以7.4 mg的产率得到(2S,3S,4aR,5S,8aR)-3',3',4a,5-tetramethylspiro[1,2,4,5,6,7,8,8a-octahydronaphthalene-3,2'-oxirane]-2-ol
  参考文献：
  名称：

  Structures of Fukinone Epoxides. Configuration, Conformation, and CD Spectra

  摘要：

  The configuration and conformation of two diastereoisomeric fukinone epoxides were unambiguously established by NMR (NOESY), CD, and X-ray crystallographic analyses of their derivatives. The data show the absolute configurations of exo alpha,beta-epoxy ketones can be predicted by an octant rule, not by a Reverse Octant Rule.

  DOI：

  10.3987/com-10-s(e)118
• 作为产物：
  描述：

  蜂斗菜酮 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以12.2 mg的产率得到(3R,4aR,5S,8aR)-3',3',4a,5-tetramethylspiro[4,5,6,7,8,8a-hexahydro-1H-naphthalene-3,2'-oxirane]-2-one
  参考文献：
  名称：

  Structures of Fukinone Epoxides. Configuration, Conformation, and CD Spectra

  摘要：

  The configuration and conformation of two diastereoisomeric fukinone epoxides were unambiguously established by NMR (NOESY), CD, and X-ray crystallographic analyses of their derivatives. The data show the absolute configurations of exo alpha,beta-epoxy ketones can be predicted by an octant rule, not by a Reverse Octant Rule.

  DOI：

  10.3987/com-10-s(e)118

文献信息

• The Transformations of Terpene Eetones by Oxygen. II. The Base-catalyzed Autoxidation of Pulegone and Fukinone and Their Dihydro Compounds
  作者：Akio Horinaka、Eiyu Yo、Otoji Mori、Keizo Naya

  DOI：10.1246/bcsj.52.2372

  日期：1979.8

  Upon autoxidation in alkaline media, pulegone and fukinone (2) gave pairs of hydroxy ketones respectively as the major products; also, hydroxyeremophilone was isolated as its acetate from 2. On the other hand, their dihydro compounds afforded hydroxy ketones, diosphenols, and acids.

  在碱性介质中自氧化时，普尔根和富基酮（2）分别生成一对羟基酮作为主要产物；此外，还从2中分离得到了羟基埃瑞莫菲酮的醋酸酯。另一方面，它们的二氢化合物则产生了羟基酮、二氧苯酚和酸。