4,4a,5,6,7,8-hexahydro-5β-hydroxy-1,8aβ-dimethyl-7β-(1-methylethenyl)-2(3H)-naphthalenone | 90665-81-9

• 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: 4,4a,5,6,7,8-hexahydro-5β-hydroxy-1,8aβ-dimethyl-7β-(1-methylethenyl)-2(3H)-naphthalenone
• 英文别名: (+)-(7S,9S,10S)-9β-hydroxyeudesma-4,11-dien-3-one；(4aS,5S,7S)-5-hydroxy-1,4a-dimethyl-7-prop-1-en-2-yl-3,4,5,6,7,8-hexahydronaphthalen-2-one
• CAS: 90665-81-9
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: MFRDGLQJGHWBQZ-CQDKDKBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,4a,5,6,7,8-hexahydro-5β-hydroxy-1,8aβ-dimethyl-7β-(1-methylethenyl)-2(3H)-naphthalenone 在 三正丁基氢锡 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 5.0h， 生成 α-香附酮
  参考文献：
  名称：

  Synthesis of homochiral α-cyperone via enantioselective catalysis

  摘要：

  The title sesquiterpene was obtained in a five-step synthesis starting from an achiral substrate: oxycarvone. Enantioselectivity is due to a phenylalanine-catalyzed intramolecular aldol reaction.

  DOI：

  10.1016/s0957-4166(00)80168-8
• 作为产物：
  描述：

  2-甲基-5-(1-甲基乙烯基)-1,3-环己二酮 在 sodium tetrahydroborate 、 高氯酸 、 L-苯丙氨酸 作用下， 以 乙醇 为溶剂， 反应 48.0h， 生成 4,4a,5,6,7,8-hexahydro-5β-hydroxy-1,8aβ-dimethyl-7β-(1-methylethenyl)-2(3H)-naphthalenone
  参考文献：
  名称：

  Synthesis of homochiral α-cyperone via enantioselective catalysis

  摘要：

  The title sesquiterpene was obtained in a five-step synthesis starting from an achiral substrate: oxycarvone. Enantioselectivity is due to a phenylalanine-catalyzed intramolecular aldol reaction.

  DOI：

  10.1016/s0957-4166(00)80168-8

文献信息

• Stereochemistry-59
  作者：Claude Agami、Franck Meynier、Catherine Puchot、Jean Guilhem、Claudine Pascard

  DOI：10.1016/s0040-4020(01)91242-6

  日期：1984.1

  sets of results give information about the mechanism of carbonyl activation by (S)-proline during asymmetric syntheses: (i) X-ray structures of two ketols produced by the proline-induced cyclization of triketones; (ii) (S)-Proline-catalyzed asymmetric dehydration of (±)-β ketols leading to optically active enones.

  两组结果给出了有关不对称合成过程中（S）-脯氨酸羰基活化机理的信息：（i）脯氨酸诱导的三酮环化生成的两种酮醇的X射线结构；（ii）（S）-脯氨酸催化的（±）-β酮醇的不对称脱水，导致旋光的烯酮。
• A Facile Total Synthesis of (±)-Selina-3, 11-Dien-9-Ol
  作者：Lijun Liu、Zhaoming Xiong、Fajun Nan、Tongshuang Li、Yulin Li

  DOI：10.1080/00397919508015874

  日期：1995.7

  Abstract A facile total synthesis of (±)-selina-3, 11-dien-9-ol (1) has been described. The key step is the one-pot reductive deoxygenation of α, β-unsaturated p-tosylhydrazone and reduction of 9-carbonyl of 9 with sodium borohydride.

  摘要 已经描述了 (±)-selina-3, 11-dien-9-ol (1) 的简便全合成。关键步骤是 α, β-不饱和对甲苯磺酰腙的一锅还原脱氧和用硼氢化钠还原 9 的 9-羰基。
• Studies on the Dehydrogenation of 9-Oxygenated-eudesma-4-en-3-ones with DDQ
  作者：Lijun Liu、Fajun Nan、Zhaoming Xiong、Tongshuang Li、Yulin Li

  DOI：10.1080/00397919608003648

  日期：1996.2

  9-Acetoxy-eudesma-4,11-dien-3-ones (4a, 4b) and 9-acetoxy-14-noreudesma-4,11-dien-3-ones (5a, 5b) were treated with DDQ in dioxane to yield normal 1,2-dehydro-products, whereas 14-noreudesma-4,11-dien-3,9-diones (2a, 2b) afforded a rearranged aromatic product, 1-hydroxy-15-noreudesma-1, 3, 5 (10), 11-tetraen-9-one (3). No reaction was observed by treatment of eudesma-4,11-dien-3,9-diones (1a, 1b) with DDQ under the same conditions. The effect of 10-methyl configuration on this reaction is also discussed.
• AGAMI, C.;MEYNIER, F.;PUCHOT, C.;GUILHEM, J.;PASCARD, C., TETRAHEDRON, 1984, 40, N 6, 1031-1038
  作者：AGAMI, C.、MEYNIER, F.、PUCHOT, C.、GUILHEM, J.、PASCARD, C.

  DOI：——

  日期：——
• The Enantioselective Synthesis of (+)-Selina-3, 11-Dien-9-ol
  作者：Jiong Yang、Zhaoming Xiong、Yonggang Chen、Yulin Li

  DOI：10.1080/00397919708005005

  日期：1997.9

  The title compound 1 was enantioselectively synthesized from oxycarvone in nine steps with an overall yield of 15%. The key step involves the p-toluenesulfonhydrazide assisted diastereoselective reductive rearrangement of allylic alcohol.