(4aR,5S,7S)-4,4a,5,6,7,8-hexahydro-7-isopropenyl-4a-methyl-5-(prop-2'-enyl)-naphthalene-2(3H)-one | 160837-39-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aR,5S,7S)-4,4a,5,6,7,8-hexahydro-7-isopropenyl-4a-methyl-5-(prop-2'-enyl)-naphthalene-2(3H)-one
• 英文别名: (4aR,5S,7S)-4a-methyl-7-prop-1-en-2-yl-5-prop-2-enyl-3,4,5,6,7,8-hexahydronaphthalen-2-one
• CAS: 160837-39-8
• 化学式: C₁₇H₂₄O
• 分子量: 244.377
• InChiKey: DKMIDRORSJPUCI-GRDNDAEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 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,5S,7S)-4,4a,5,6,7,8-hexahydro-7-isopropenyl-4a-methyl-5-(prop-2'-enyl)-naphthalene-2(3H)-one 、 碘甲烷 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 1.0h， 以88%的产率得到(4aR,5S,7S)-3,4,4a,5,6,7-hexahydro-7-isopropenyl-5-(prop-2'-enyl)-1,1,4a-trimethylnaphthalene-2(1H)-one
  参考文献：
  名称：

  由S-（+）-香芹酮全合成（-）-Ambrox®（第6部分）

  摘要：

  将氰化物和烯丙基亲核试剂共轭添加到S-（+）-香芹酮中，然后与甲基乙烯基酮环化，得到立体选择性的取代的十碳杂萘2和3。既decalones转化到（ - ） -艾姆罗克斯®经由侧链，甲基化，转换的异丙烯基和环化的修饰。

  DOI：

  10.1016/s0040-4020(01)89625-3
• 作为产物：
  描述：

  (3S,5S)-5-isopropenyl-2-methyl-3-(prop-2'-enyl)-1-trimethylsilyloxy-cyclohex-1-ene 在 硝基甲烷 、 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 异丙醇 为溶剂， 反应 22.5h， 生成 (4aR,5S,7S)-4,4a,5,6,7,8-hexahydro-7-isopropenyl-4a-methyl-5-(prop-2'-enyl)-naphthalene-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

• Total synthesis of (−)-Ambrox® from S-(+)-carvone (part 6)
  作者：Anja A. Verstegen-Haaksma、Henk J. Swarts、Ben J.M. Jansen、Aede de Groot

  DOI：10.1016/s0040-4020(01)89625-3

  日期：1994.1

  Conjugate addition of cyanide and allyl nucleophiles to S-(+)-carvone followed by annulation with methyl vinyl ketone gave the substituted decalones 2 and 3 stereoselectively. Both decalones were transformed into (−)-Ambrox®via modification of the sidechain, methylation, conversion of the isopropenyl group and cyclization.

  将氰化物和烯丙基亲核试剂共轭添加到S-（+）-香芹酮中，然后与甲基乙烯基酮环化，得到立体选择性的取代的十碳杂萘2和3。既decalones转化到（ - ） -艾姆罗克斯®经由侧链，甲基化，转换的异丙烯基和环化的修饰。
• 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.