8α-hydroxy-Δ¹⁽⁹⁾-octalone-2 | 67034-88-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8α-hydroxy-Δ¹⁽⁹⁾-octalone-2
• 英文别名: 8α-Hydroxy-4,4a,5,6,7,8-hexahydro-2(3H)-naphtalenon；(4aR,8R)-8-hydroxy-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one
• CAS: 67034-88-2；67034-89-3；142597-03-3；142597-04-4
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: HDAJZTYFWFECKV-GMSGAONNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.44
• 重原子数：
  12.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  8α-hydroxy-Δ¹⁽⁹⁾-octalone-2 在 吡啶 、 正丁基锂 、 (1,1'-双(二苯基膦)二茂铁)二氯化镍 、 potassium iodide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 4,4a,5,6,7,8-六氢-3H-萘-2-酮
  参考文献：
  名称：

  Arylation of 8-Acetoxyoctalenone in a Nickel-Catalyzed Coupling Reaction with Lithium Arylborates

  摘要：

  In order to find a suitable organometallic compound and a catalyst for the arylation of 8-acetoxyoctalenone 4 (a stereoisomeric mixture of 4 alpha and 4 beta), phenylation was first-investigated with PhZnX (7: X = Cl; 8: X = Br)/Pd or Ni cat., PhSnBu3 (9)/Pd cat. and LiCl, and [PhB(Bu)(OCHMeCHMeO)]Li (10a)/Ni cat. Berate 10a provided the desired product 11a with high stereoselectivity. The stereochemical outcome was irrespective of the stereochemistry of the acetoxy group in 4. Four more aryl groups, p-R-C6H4 (R = Me, MeO, Ph, and Me2N), were installed stereoselectively with this method.

  DOI：

  10.1002/1099-0690(200010)2000:20<3393::aid-ejoc3393>3.0.co;2-c
• 作为产物：
  描述：

  4,4a,5,6,7,8-六氢-3H-萘-2-酮 生成 8α-hydroxy-Δ¹⁽⁹⁾-octalone-2
  参考文献：
  名称：

  Holland,H.L.; Diakow,P.R.P., Canadian Journal of Chemistry, 1978, vol. 56, p. 694 - 702

  摘要：

  DOI：

文献信息

• Angular hydroxymethylation of decalin systems
  作者：J. Lejeune、J.Y. Lallemand

  DOI：10.1016/s0040-4039(00)79576-1

  日期：1992.5

  Decalin systems with alpha- and beta-allylic alcohol groups have been subjected to the Stork silyl methyl radical cyclisation reaction to introduce a hydroxymethyl function at the angular position.
• Holland,H.L.; Diakow,P.R.P., Canadian Journal of Chemistry, 1978, vol. 56, p. 694 - 702
  作者：Holland,H.L.、Diakow,P.R.P.

  DOI：——

  日期：——
• Arylation of 8-Acetoxyoctalenone in a Nickel-Catalyzed Coupling Reaction with Lithium Arylborates
  作者：Yuichi Kobayashi、Michiko Ito

  DOI：10.1002/1099-0690(200010)2000:20<3393::aid-ejoc3393>3.0.co;2-c

  日期：2000.10

  In order to find a suitable organometallic compound and a catalyst for the arylation of 8-acetoxyoctalenone 4 (a stereoisomeric mixture of 4 alpha and 4 beta), phenylation was first-investigated with PhZnX (7: X = Cl; 8: X = Br)/Pd or Ni cat., PhSnBu3 (9)/Pd cat. and LiCl, and [PhB(Bu)(OCHMeCHMeO)]Li (10a)/Ni cat. Berate 10a provided the desired product 11a with high stereoselectivity. The stereochemical outcome was irrespective of the stereochemistry of the acetoxy group in 4. Four more aryl groups, p-R-C6H4 (R = Me, MeO, Ph, and Me2N), were installed stereoselectively with this method.