4,5-Benzospiro<3.5>nonan-1-on | 42436-99-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 4,5-Benzospiro<3.5>nonan-1-on
• 英文别名: 4,5-Benzospiro<3,5>nonan-6-on；3',4'-dihydro-2'h-spiro[cyclobutane-1,1'-naphthalen]-2-one；3',4'-Dihydro-2'H-spiro[cyclobutane-1,1'-naphthalen]-2-one；spiro[2,3-dihydro-1H-naphthalene-4,2'-cyclobutane]-1'-one
• CAS: 42436-99-7
• 化学式: C₁₃H₁₄O
• 分子量: 186.254
• InChiKey: CLIQREISWGNXGV-UHFFFAOYSA-N

物化性质

• 沸点：
  325.6±21.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  4,5-Benzospiro<3.5>nonan-1-on 在 pyridinium hydrobromide perbromide 、 溶剂黄146 作用下， 生成 cis-3,4-Benzo-1-bromo-1-carbomethoxy-spiro<2.5>octan
  参考文献：
  名称：

  New synthetic reactions. Geminal and reductive alkylations

  摘要：

  DOI：

  10.1021/ja00841a037
• 作为产物：
  描述：

  在 lithium perchlorate 作用下， 以 苯 为溶剂， 反应 12.0h， 以94 mg的产率得到4,5-Benzospiro<3.5>nonan-1-on
  参考文献：
  名称：

  Catalytic and Regioselective Ring Expansion of Arylcyclobutanones with Trimethylsilyldiazomethane. Ligand-Dependent Entry to β-Ketosilane or Enolsilane Adducts

  摘要：

  Divergent reactivity is uncovered in the homologation of arylcyclobutanones with trimethylsilyldiazomethane. With Sc(OTf)(3) as catalyst, enolsilanes are obtained with a high preference for methylene migration. By contrast, Sc(hfac)(3) gives beta-ketosilanes with both regio- and diastereocontrol. Each adduct affords the cyclopentanone upon hydrolysis.

  DOI：

  10.1021/ol101136a

文献信息

• New synthetic reactions. X. Versatile cyclobutanone (spiroannelation) and .gamma.-butyrolactone (lactone annelation) synthesis
  作者：Barry M. Trost、Mitchell J. Bogdanowicz

  DOI：10.1021/ja00797a037

  日期：1973.8
• Organic photochemistry. 40. Photochemistry of bichromophoric molecules. Photochemistry and photophysics of 2-methylenebenzonorbornene and related nonconjugated aryl olefins in nonprotic media
  作者：Frank Scully、Tom Nylund、Fred Palensky、Harry Morrison

  DOI：10.1021/ja00491a037

  日期：1978.11
• New synthetic reactions. Geminal alkylation via .alpha.-trimethylenedithiocyclobutanones
  作者：Barry M. Trost、Margaret Preckel、Louis M. Leichter

  DOI：10.1021/ja00841a038

  日期：1975.4
• Catalytic and Regioselective Ring Expansion of Arylcyclobutanones with Trimethylsilyldiazomethane. Ligand-Dependent Entry to β-Ketosilane or Enolsilane Adducts
  作者：Jennifer A. Dabrowski、David C. Moebius、Andrew J. Wommack、Anne F. Kornahrens、Jason S. Kingsbury

  DOI：10.1021/ol101136a

  日期：2010.8.20

  Divergent reactivity is uncovered in the homologation of arylcyclobutanones with trimethylsilyldiazomethane. With Sc(OTf)(3) as catalyst, enolsilanes are obtained with a high preference for methylene migration. By contrast, Sc(hfac)(3) gives beta-ketosilanes with both regio- and diastereocontrol. Each adduct affords the cyclopentanone upon hydrolysis.
• New synthetic reactions. Geminal and reductive alkylations
  作者：Barry M. Trost、Mitchell J. Bogdanowicz、Jeffrey Kern

  DOI：10.1021/ja00841a037

  日期：1975.4