3,4-dihydro-2-propargyl-1(2H)naphthalenone | 27419-27-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 3,4-dihydro-2-propargyl-1(2H)naphthalenone
• 英文别名: 2--tetral-1-on；2H-3,4-Dihydro-2-propargyl-naphthalin-1-on；2-Propargyl-tetralon-1；2-prop-2-ynyl-3,4-dihydro-2H-naphthalen-1-one
• CAS: 27419-27-8
• 化学式: C₁₃H₁₂O
• 分子量: 184.238
• InChiKey: SAZWQJWBBCVELJ-UHFFFAOYSA-N

物化性质

• 沸点：
  301.5±11.0 °C(Predicted)
• 密度：
  1.079±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  3,4-dihydro-2-propargyl-1(2H)naphthalenone 在 甲醇 、 氢氧化钾 、 硫酸 、 mercury(II) sulfate 作用下， 生成 3,3a,4,5-tetrahydro-2H-benzinden-2-one
  参考文献：
  名称：

  Brown,E. et al., Bulletin de la Societe Chimique de France, 1971, p. 2195 - 2203

  摘要：

  DOI：
• 作为产物：
  描述：

  1-氧代-1,2,3,4-四氢萘-2-甲醛 、 3-溴丙炔 在 sodium 作用下， 以 苯 为溶剂， 生成 3,4-dihydro-2-propargyl-1(2H)naphthalenone
  参考文献：
  名称：

  Brown,E. et al., Bulletin de la Societe Chimique de France, 1971, p. 2195 - 2203

  摘要：

  DOI：

文献信息

• Intramolecular Schmidt Reaction of Vinyl Azides with Cyclic Ketones
  作者：Peng Chen、Chu-Han Sun、Yu Wang、Ying Xue、Chen Chen、Mei-Hua Shen、Hua-Dong Xu

  DOI：10.1021/acs.orglett.8b00395

  日期：2018.3.16

  tethered with a vinyl azide group undergo a Schmidt-hydrolysis sequence to give secondary lactams bearing a ketone side chain. Secondary lactams are obtained in a regioselective manner that is not possible in a conventional Schimdt reaction. In addition to the well-documented C-2 nucleophilicity, the N nucleophilicity of vinyl azide disclosed in this work opens a new direction for reaction invention involving

  与叠氮乙烯基连接的环状酮经过施密特水解序列，得到带有酮侧链的仲内酰胺。仲内酰胺是以区域选择性的方式获得的，这在常规的Schimdt反应中是不可能的。除了有据可证的C-2亲核性，这项工作中公开的叠氮化乙烯基的N亲核性为涉及叠氮化乙烯基的反应发明开辟了新的方向。
• Brown,E. et al., Bulletin de la Societe Chimique de France, 1972, p. 212 - 220
  作者：Brown,E. et al.

  DOI：——

  日期：——
• On the π-π interaction in the benzylation of ketones
  作者：Enrique Díez-Barra、Sonia Merino、Prado Sánchez-Verdú、José Torres

  DOI：10.1016/s0040-4020(97)00724-2

  日期：1997.8

  The benzylation of a set of nine ketones provides enough information to establish how the ketone structure affects the existence of a pi-pi interaction. The presence of a phenyl moiety starting from the alpha-carbon atom and flexibility in cyclic ketones are structural features required for effective interactions. The pi-pi interaction is controlled by a polar-pi effect. Stronger interaction is achieved when slight electronwithdrawing groups are present in both pi-system. This results is explained by the predominance of the sigma-pi shells attractive interaction in an edge-to-face geometry. (C) 1997 Elsevier Science Ltd.
• Enantioselective oxidation of aromatic ketones by molecular oxygen, catalyzed by chiral monoaza-crown ethers
  作者：Erik F.J. de Vries、Lisette Ploeg、Marcello Colao、Johannes Brussee、Arne van der Gen

  DOI：10.1016/0957-4166(95)00138-f

  日期：1995.5

  Chiral monoaza-15-crown-5 ethers 3a-c and monoaza-18-crown-6 ethers 3d-f have been synthesized from optically active diethanolamines in moderate to good yields. One of these crown ethers, i.e. 3a, proved to be both an efficient and a selective phase transfer catalyst in the asymmetric oxidation of aromatic ketones:by molecular oxygen. Yields of the oxidation reaction were high and enantiomeric ! excesses of up to 72% could be obtained. To account for the remarkable differences in asymmetric induction between the crown ethers tested, a model for the:structure of the transition stare was proposed.
• Phase-Transfer-Catalyzed Enantioselective α-Hydroxylation of Acyclic and Cyclic Ketones with Oxygen
  作者：Sui-Boon Derek Sim、Min Wang、Yu Zhao

  DOI：10.1021/acscatal.5b00583

  日期：2015.6.5

  An efficient and enantioselective alpha-hydroxylation of acyclic as well as cyclic ketones using molecular oxygen has been developed. This simple catalytic procedure uses a readily available phase transfer catalyst and produces a wide range of valuable tertiary a-hydroxy ketones in good to excellent enantiopurity.