(-)-(4aR,8aR)-3,4,4a,5,6,7,8,8a-octahydro-4a,8,8-trimethylnaphthalene-2(1H)-one | 112572-62-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-(4aR,8aR)-3,4,4a,5,6,7,8,8a-octahydro-4a,8,8-trimethylnaphthalene-2(1H)-one
• 英文别名: (4aR,8aS)-3,4,4a,5,6,7,8,8a-octahydro-4a,8,8-trimethyl-2(1H)-naphthalenone；(1S,6R)-6,10,10-trimethylbicyclo<4.4.0>decan-3-one；(4aR,8aS)-(-)-4a,8,8-trimethyldecahydronaphthalen-2-one；trans-3-Oxo-5,5,8a-trimethyl-decalin；(4aR,8aS)-4a,8,8-trimethyl-3,4,5,6,7,8a-hexahydro-1H-naphthalen-2-one
• CAS: 112572-62-0
• 化学式: C₁₃H₂₂O
• 分子量: 194.317
• InChiKey: BOVNKOFPMOPKKL-WCQYABFASA-N

物化性质

• 熔点：
  39 °C
• 沸点：
  260.2±8.0 °C(predicted)
• 密度：
  0.933±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (-)-(4aR,8aR)-3,4,4a,5,6,7,8,8a-octahydro-4a,8,8-trimethylnaphthalene-2(1H)-one 在 palladium on activated charcoal sodium hydroxide 、 重铬酸吡啶 、 氢气 、 双氧水 、 pyridinium hydrobromide perbromide 、 lithium carbonate 、 一水合肼 、 溶剂黄146 、 lithium bromide 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.83h， 生成 (+-)-5,5,8a-trimethyl-(4ar,8at)-octahydro-naphthalen-1-one
  参考文献：
  名称：

  从S-（+）-香芹酮中合成手性十烯酮，（-）-1,1,4a-三甲基-2-癸醛和（+）-地臭（第3部分）

  摘要：

  由S-（+）-香芹酮合成胆固醇生物合成抑制剂（-），1,1,4a-三甲基-2-癸醛（4），手性十碳六烯酮6和7和（+）-土臭素（9）。 （ - - ） - S的dihydrocarvone接着进行甲基化，得到化合物8，其被用作关键中间体用于合成decalol 4和酮5。短异构臭氧化序列被用于除去异丙烯基的开发酮6和（十）十足动物（9）通过羰基转座从十全十（5）中获得7个。（+）-geosmin（9使用Criegee重排除去异丙烯基而合成）。

  DOI：

  10.1016/s0040-4020(01)88303-4
• 作为产物：
  描述：

  8,8,10-Trimethyl-trans-Δ⁶-oktalon-(2) 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以93%的产率得到(-)-(4aR,8aR)-3,4,4a,5,6,7,8,8a-octahydro-4a,8,8-trimethylnaphthalene-2(1H)-one
  参考文献：
  名称：

  Mori, Kenji; Takaishi, Hideo, Liebigs Annalen der Chemie, 1989, p. 695 - 698

  摘要：

  DOI：

文献信息

• The conversion of (−)- and (+)-dihydrocarvone into chiral intermediates for the synthesis of (−)-polygodial, (−)-warburganal and (−)-muzigadial
  作者：Ben.J.M. Jansen、Jacoba A. Kreuger、Aede De Groot

  DOI：10.1016/0040-4020(89)80143-7

  日期：1989.1

  (−)-Dihydrocarvone was converted into (−)-(4aR, 8aR)-3,4,4a,5,6,7,8,8a-octahydro-4a, 8,8-trimethylnaphthalene-2(H)-one (1) via an efficient route in which a Wolff-Kishner reduction, accompanied with a double bond isomerisation brought on a major simplification. Ketone 1 is a suitable intermediate for the syntheses of the insectantifeedants (−)-polygodial and (−)-warburganal. (+)-Dihydrocarvone was

  （-）-二氢香芹酮被转化为（-）-（4aR，8aR）-3,4,4a，5,6,7,8,8a-八氢-4a，8,8-三甲基萘-2（H）- （1）通过沃尔夫-基什纳（Wolff-Kishner）还原并伴有双键异构化的有效途径，大大简化了反应。酮1是合成昆虫抗饲料（-）-多头体和（-）-warburganal的合适中间体。（+）-二氢香芹酮转化为（+）-（4aR，7S，8aR）-4a，7-二甲基-8-亚甲基-3，4,4a，5,6,7,8,8a-八氢萘-2（1H）-一（2），是合成（-）-穆济加迪尔的中间体酮。
• Ring differentiation of the trans-decahydronaphthalene system via chemo-enzymatic dissymmetrization of its σ-symmetric glycol: Synthesis of a highly functionalized chiral building block for the terpene synthesis
  作者：Naoki Toyooka、Akira Nishino、Takefumi Momose

  DOI：10.1016/0040-4039(93)88079-x

  日期：1993.7

  The asymmetric ring differentiation by lipase-catalyzed transesterification of a meso decahydronaphthalenediol (1) was accomplished in extremely high optical and chemical yield. The absolute stereochemistry of the corresponding mono-acetate(-)-2 was determined by its conversion into a decalone [(-)-31 and to an octalone [(+)-4], which were key intermediates for the synthesis of (-)-polygodial, (-)-warburganal, and (-)-drimenin.
• Enantiodivergent synthesis of a decalin type of chiral building blocks and their application to terpenoid synthesis
  作者：Naoki Toyooka、Akira Nishino、Takefumi Momose

  DOI：10.1016/s0040-4020(97)00315-3

  日期：1997.5

  An enantiomeric pair of a decalin type of chiral building blocks bearing an oxygenated angular substituent has been synthesized by the lipase-mediated ring differentiation of a meso decahydronaphthalene glycol system Its synthetic utility has been demonstrated by the formal synthesis of (-)-polygodial, (-)-warburganal, (-)-drimenin, and (-)-elemol. (C) 1997 Elsevier Science Ltd.
• New lactones from tobacco
  作者：Tore. Pettersson、Ann Marie. Eklund、Inger. Wahlberg

  DOI：10.1021/jf00035a052

  日期：1993.11

  Thirteen lactones (1-13) have been isolated from an extract of sun-cured leaves of Greek tobacco by using HPLC methods. All but four of these (1-9) are new natural products. They have been identified as 3-(4-methyl-1-pentyl)-2-buten-4-olide (1), 3-isopropyl-2-penten-4-olide (2),3-ethyl-4-methyl-2-penten-4-olide (3), 4-methyl-3-(3-oxo-1-butyl)-2-penten-4-olide (4), 3-methyl-7-oxo-2-octen-4-olide (5), 4-(5-methyl-2-furyl)pentan-4-olide (6), (3R*,4R*,7R*)-3,7-epoxy-4,8-dimethyl-8-nonen-4-olide (7), 3-isopropyl-2,4-pentadien-5-olide (8), and (1S,7R)-4-oxa-7,11,11-trimethylbicyclo[5.4.0]undecan-3-one (9) by spectral methods, 2D NMR being a helpful tool. The syntheses of two of the lactones (1 and 9) are reported, and the plausible biogenesis of the new lactones is discussed. (Z)-6-Nonen-4-olide (10) and 5-methyl-4-hexanolide (11), now also isolated, are new to tobacco, while two 3-methyl-4-pentanolides (12 and 13), previously known as tobacco constituents, have now been identified as the 3R,4R- and 3R,4S-isomers by comparison of their optical rotations and spectral data with those of corresponding synthetic samples.
• JANSEN, BEN. J. M.;KREUGER, JACOBA A.;DE, GROOT AEDE, TETRAHEDRON, 45,(1989) N, C. 1447-1452
  作者：JANSEN, BEN. J. M.、KREUGER, JACOBA A.、DE, GROOT AEDE

  DOI：——

  日期：——