trans-2,3,3a,4,9,9a-Hexahydro-1H-benzinden-4-one | 99098-08-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: trans-2,3,3a,4,9,9a-Hexahydro-1H-benzinden-4-one
• 英文别名: (3aR,9aS)-1,2,3,3a,9,9a-hexahydrocyclopenta[b]naphthalen-4-one
• CAS: 99098-08-5
• 化学式: C₁₃H₁₄O
• 分子量: 186.254
• InChiKey: XWFNXVFAEJTIAW-CMPLNLGQSA-N

物化性质

• 熔点：
  62-63 °C
• 沸点：
  311.9±12.0 °C(Predicted)
• 密度：
  1.115±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  trans-2,3,3a,4,9,9a-Hexahydro-1H-benzinden-4-one 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以85%的产率得到trans-2,3,3a,4,9,9a-Hexahydro-1H-benzinden-4-ol
  参考文献：
  名称：

  Regioselective Aryl Radical Cyclization. 1. Stereocontrolled Synthesis of Linearly Condensed Hydroaromatic Carbocyclic Systems through 6-endo-Ring Closures

  摘要：

  The stereocontrolled synthesis of trans-octahydroanthracenes 3, 11a-c, and 14a-c and trans-octahydro-5aH-cyclohepta[b] naphthalene (27) through implementation of an efficient and highly regioselective 6-endo-trig-aryl radical cyclization of the respective 2-(o-bromoaryl)-1-methylenecyclohexanes 2, 10a-c, and 13a-c and 2-(o-bromobenzyl)-1-methylenecycloheptane (41) with tri-n- butyltin-hydride-is described. The radical cyclization of 2-(o-bromobenzyl)-1-methylenecyclopentane (43), in contrast, produced a mixture of the cis- and trans-hexahydro-1H-benz[f]indenes (38) and (37).

  DOI：

  10.1021/jo00089a009
• 作为产物：
  描述：

  2-Benzyl-1-(hydroxymethyl)cyclopentane 在 jones reagent 、 sodium methylate 作用下， 以 丙酮 为溶剂， 反应 4.75h， 生成 trans-2,3,3a,4,9,9a-Hexahydro-1H-benzinden-4-one
  参考文献：
  名称：

  Regioselective Aryl Radical Cyclization. 1. Stereocontrolled Synthesis of Linearly Condensed Hydroaromatic Carbocyclic Systems through 6-endo-Ring Closures

  摘要：

  The stereocontrolled synthesis of trans-octahydroanthracenes 3, 11a-c, and 14a-c and trans-octahydro-5aH-cyclohepta[b] naphthalene (27) through implementation of an efficient and highly regioselective 6-endo-trig-aryl radical cyclization of the respective 2-(o-bromoaryl)-1-methylenecyclohexanes 2, 10a-c, and 13a-c and 2-(o-bromobenzyl)-1-methylenecycloheptane (41) with tri-n- butyltin-hydride-is described. The radical cyclization of 2-(o-bromobenzyl)-1-methylenecyclopentane (43), in contrast, produced a mixture of the cis- and trans-hexahydro-1H-benz[f]indenes (38) and (37).

  DOI：

  10.1021/jo00089a009

文献信息

• .alpha.,.alpha.-Dimethoxy-o-xylylene [5-(dimethoxymethylene)-6-methylene-1,3-cyclohexadiene]: formation by 1,4-elimination and electrocyclic routes and reactions
  作者：Randall J. Moss、Russell O. White、Bruce Rickborn

  DOI：10.1021/jo00225a031

  日期：1985.12
• MOSS, R. J.;WHITE, R. O.;RICKBORN, B., J. ORG. CHEM., 1985, 50, N 25, 5132-5139
  作者：MOSS, R. J.、WHITE, R. O.、RICKBORN, B.

  DOI：——

  日期：——