(-)-(4aR,7S)-4,4a,5,6,7,8-hexahydro-7-isopropenyl-4a-methylnaphthalene-2(3H)-one | 124753-20-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-(4aR,7S)-4,4a,5,6,7,8-hexahydro-7-isopropenyl-4a-methylnaphthalene-2(3H)-one
• 英文别名: (4aR,7S)-4a-methyl-7-prop-1-en-2-yl-3,4,5,6,7,8-hexahydronaphthalen-2-one
• CAS: 124753-20-4
• 化学式: C₁₄H₂₀O
• 分子量: 204.312
• InChiKey: NBEKVDFBSCFXPP-SMDDNHRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 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,7S)-4,4a,5,6,7,8-hexahydro-7-isopropenyl-4a-methylnaphthalene-2(3H)-one 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 9α,10α-Dimethyl-7α-isopropyl-decalon-(2)
  参考文献：
  名称：

  Methylation of 10-methyl-1(9)-octal-2-ones by organocopper reagents

  摘要：

  DOI：

  10.1021/jo01266a079
• 作为产物：
  描述：

  dihydrocarvone 在 硝基甲烷 、 三氟化硼乙醚 、 sodium methylate 、 三乙胺 、 sodium iodide 作用下， 以 甲醇 、 二氯甲烷 、 异丙醇 、 乙腈 为溶剂， 反应 9.5h， 生成 (-)-(4aR,7S)-4,4a,5,6,7,8-hexahydro-7-isopropenyl-4a-methylnaphthalene-2(3H)-one
  参考文献：
  名称：

  S-(+)-carvone as starting material in synthesis (part 4). Conjugate addition of cyanide and Grignard nucleophiles followed by annulation to functionalized decalones.

  摘要：

  Two conjugate addition/annulation methodologies for S-(+)-carvone are reported. The conjugate addition of Grignard reagents, followed by the Lewis acid catalyzed Michael reaction of the intermediate silyl enol ethers with MVK and cyclization of the diketones, gave decalones 2a-d stereoselectively and in good yield. The conjugate addition of cyanide anion followed by base catalyzed Robinson annulation with MVK and dehydration gave decalone 2e stereoselectively in very high yield.

  DOI：

  10.1016/s0040-4020(01)89623-x

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。
• 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：——
• S-(+)-carvone as starting material in synthesis (part 4). Conjugate addition of cyanide and Grignard nucleophiles followed by annulation to functionalized decalones.
  作者：Anja A. Verstegen-Haaksma、Henk J. Swarts、Ben J.M. Jansen、Aede de Groot

  DOI：10.1016/s0040-4020(01)89623-x

  日期：1994.1

  Two conjugate addition/annulation methodologies for S-(+)-carvone are reported. The conjugate addition of Grignard reagents, followed by the Lewis acid catalyzed Michael reaction of the intermediate silyl enol ethers with MVK and cyclization of the diketones, gave decalones 2a-d stereoselectively and in good yield. The conjugate addition of cyanide anion followed by base catalyzed Robinson annulation with MVK and dehydration gave decalone 2e stereoselectively in very high yield.
• Methylation of 10-methyl-1(9)-octal-2-ones by organocopper reagents
  作者：James A. Marshall、Heide Roebke

  DOI：10.1021/jo01266a079

  日期：1968.2