2-(2-(1-naphthyl)-2-oxoethyl)cyclohexanone | 127931-52-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(2-(1-naphthyl)-2-oxoethyl)cyclohexanone
• 英文别名: 2-(2-Naphthyl-2-oxoethyl)cyclohexanone；2-[2-(1-Naphthyl)-2-oxoethyl]cyclohexanone；2-(2-naphthalen-1-yl-2-oxoethyl)cyclohexan-1-one
• CAS: 127931-52-6
• 化学式: C₁₈H₁₈O₂
• 分子量: 266.34
• InChiKey: DSCASSWLTLAVBJ-UHFFFAOYSA-N

物化性质

• 沸点：
  451.5±18.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (bicyclo[4.1.0]heptan-1-yloxy)trimethylsilane 、 1-萘甲酰氯 在 亚磷酸三苯酯 、 钯 一氧化碳 作用下， 以 六甲基磷酰三胺 为溶剂， 100.0 ℃ 、1.01 MPa 条件下， 反应 20.0h， 以46%的产率得到2-(2-(1-naphthyl)-2-oxoethyl)cyclohexanone
  参考文献：
  名称：

  Palladium- and platinum-catalyzed reaction of siloxycyclopropanes with acid chlorides. A homoenolate route to 1,4-dicarbonyl compounds

  摘要：

  DOI：

  10.1016/s0040-4039(01)89016-x

文献信息

• Synthesis of 1,4-keto esters and 1,4-diketones via palladium-catalyzed acylation of siloxycyclopropanes. Synthetic and mechanistic studies
  作者：Tsutomu Fujimura、Satoshi Aoki、Eiichi Nakamura

  DOI：10.1021/jo00008a043

  日期：1991.4

  The reaction of a variety of siloxycyclopropanes with acid chlorides in the presence of a catalytic amount of a palladium/phosphine complex gives 1,4-dicarbonyl compounds to good yield. 1-Alkoxy-1-(trialkylsiloxy)-cyclopropanes react with both aromatic and aliphatic acid chlorides in chloroform to give 1,4-keto esters. Synthesis of 1,4-diketones by the acylation of 1-alkyl- or 1-aryl-1-siloxycyclopropanes has been achieved by carrying out the reaction if HMPA under 10-20 atm of carbon monoxide. Kinetics studies and product analysis revealed the unique mechanism of this reaction, which involves rate-determining cleavage of the strained cyclopropane carbon-carbon bond with a coordinatively unsaturated acylpalladium chloride complex. Ab initio calculations of hydroxylated cyclopropane model compounds showed that the unique reactivities of the siloxycyclopropanes may be correlated with the molecular orbital properties of these compounds rather than their ground-state structural properties.
• Synthesis of 1,4-dicarbonyl compounds and 4-keto pimelates by palladium-catalyzed carbonylation of siloxycyclopropanes
  作者：Satoshi Aoki、Eiichi Nakamura

  DOI：10.1016/s0040-4020(01)86434-6

  日期：1991.1

  Palladium-catalyzed reaction of a siloxycyclopropane with an aryl triflate under carbon monoxide pressure (10-20 atm) in HMPA and that with carbon monoxide in chloroform provides new synthetic routes to 1,4-dicarbonyl compounds and 4-keto pimelates, respectively. The reaction of a siloxycyclopropane with a vinyl triflate, on the other hand, gives an acyloxycyclopropane instead.
• AOKI, SATOSHI;FUJIMURA, TSUTOMU;NAKAMURA, EIICHI;KUWAJIMA, ISAO, TETRAHEDRON. LETT., 30,(1989) N7, C. 6541-6544
  作者：AOKI, SATOSHI、FUJIMURA, TSUTOMU、NAKAMURA, EIICHI、KUWAJIMA, ISAO

  DOI：——

  日期：——
• AOKI, SATOSHI;NAKAMURA, EIICHI, SYNLETT.,(1990) N2, C. 741-742
  作者：AOKI, SATOSHI、NAKAMURA, EIICHI

  DOI：——

  日期：——
• FUJIMURA, TSUTOMU;AOKI, SATOSHI;NAKAMURA, EIICHI, J. ORG. CHEM., 56,(1991) N, C. 2809-2821
  作者：FUJIMURA, TSUTOMU、AOKI, SATOSHI、NAKAMURA, EIICHI

  DOI：——

  日期：——