(4aRS,8aSR)-3,4,4a,5,6,7,8,8a-octahydro-4a,8,8-trimethylnaphthalen-2(1H)-one | 10244-80-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aRS,8aSR)-3,4,4a,5,6,7,8,8a-octahydro-4a,8,8-trimethylnaphthalen-2(1H)-one
• 英文别名: 1,1,4a-Trimethyl-trans-7-decalone；4,4,10-Trimethyl-5α-decalon-7；8,8,10-Trimethyl-trans-2-decalon；5,5,9-Trimethyl-trans-3-decalon；(4aS,8aR)-4a,8,8-Trimethyloctahydronaphthalen-2(1H)-one；(4aS,8aR)-4a,8,8-trimethyl-3,4,5,6,7,8a-hexahydro-1H-naphthalen-2-one
• CAS: 10244-80-1；16892-22-1；56712-05-1；93427-93-1；112572-62-0
• 化学式: C₁₃H₂₂O
• 分子量: 194.317
• InChiKey: BOVNKOFPMOPKKL-YPMHNXCESA-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：

  (4aRS,8aSR)-3,4,4a,5,6,7,8,8a-octahydro-4a,8,8-trimethylnaphthalen-2(1H)-one 在 sodium hydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 溶剂黄146 、 苯 为溶剂， 生成 polygonone
  参考文献：
  名称：

  Diterpenoid total synthesis, an A .far. B .far. C approach. VII. Total synthesis of DL-sugiol, DL-ferruginol, and DL-nimbiol

  摘要：

  DOI：

  10.1021/jo00913a015
• 作为产物：
  描述：

  1,1,4a-trimethyl-3,4,4a,5,6,7-hexahydronaphthalen-2(1H)-one 在 sodium chromate(VI) 、 氨 、 lithium 、 溶剂黄146 、 diethylene glycol monosodium salt 、 肼 作用下， 以 四氢呋喃 、 乙酸酐 、 二乙二醇 为溶剂， 反应 84.5h， 生成 (4aRS,8aSR)-3,4,4a,5,6,7,8,8a-octahydro-4a,8,8-trimethylnaphthalen-2(1H)-one
  参考文献：
  名称：

  Janaki, S.; Subba Rao, G. S. R., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 505 - 507

  摘要：

  DOI：

文献信息

• A Regioselective Cyclohexannulation Procedure<i>via</i>Dienamine [4 + 2] Cycloaddition. Synthesis of Functionalised Decalins
  作者：Roger L. Snowden、Simon M. Linder、Manfred Wüst

  DOI：10.1002/hlca.19890720505

  日期：1989.8.9

  A regioselective cyclohexannulation procedure, whose key step involves the [4 + 2] cycloaddition of dienamines 12–24 with methyl acrylate, allows the conversion of cycloalkanones 1–11 to bicyclic dienoates 25 – 37. The chemistry of 26 is briefly examined and, in the context of organoleptic studies concerning functionalised 5,5,9-tri-methyldecalins, the transformation of 37 to ketones 44 and 46 as well

  区域选择性cyclohexannulation过程，其关键的步骤涉及dienamines的[4 + 2]环加成12-24与丙烯酸甲酯，允许环烷酮的转化1-11双环dienoates 25 - 37。简要检查了26的化学性质，并在有关功能化5,5,9-三甲基十氢化萘的感官研究中，描述了37向酮44和46以及向乙酸酯53-56的转化。
• Synthesis of Potential Ambra Odorants: 5,5,9-trimethyldecalyl derivatives
  作者：Günther Ohloff、Ferdinand Näf、René Decorzant、Walter Thommen、Erling Sundt

  DOI：10.1002/hlca.19730560425

  日期：1973.4.25

  AbstractThe synthesis of racemic stereoisomeric compounds with the 5,5,9‐trimethyldecalin skeleton and an oxygen function at C(1), C(2), or C(3) is describedAlthough racemic decalins are described, only the enantiomer related to steroids is drawn. The projection of the decalins was chosen so as to place the angular methyl group above the plane of the molecule and the oxygen function at C(1), C(2) or C(3) on the left side, as represented by formula 1–6. The relative configuration of the substituents in decalins is designated by using the convention of the steroid series: β, meaning on the same side as the angular methyl group at C(9) and α, meaning on the side opposite from the angular methyl group. The prefix cis or trans refers to the fusion of the decalin ring system, not to the position of the substituents. . A novel general one‐step synthesis of 2‐decalones by means of acid catalyzed cyclization of acyclic or monocyclic precursors has been developed.
• Enzell,C., Acta Chemica Scandinavica (1947-1973), 1962, vol. 16, p. 1553 - 1568
  作者：Enzell,C.

  DOI：——

  日期：——
• Janaki, S.; Subba Rao, G. S. R., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 505 - 507
  作者：Janaki, S.、Subba Rao, G. S. R.

  DOI：——

  日期：——
• Diterpenoid total synthesis, an A .far. B .far. C approach. VII. Total synthesis of DL-sugiol, DL-ferruginol, and DL-nimbiol
  作者：Walter L. Meyer、George B. Clemans、Richard A. Manning

  DOI：10.1021/jo00913a015

  日期：1975.12