2-(2-phenylacetyl)cyclohexanone | 53661-37-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2-phenylacetyl)cyclohexanone
• 英文别名: 2-phenacylcyclohexanone；2-phenylacetyl-cyclohexanone；2-Phenylacetyl-cyclohexanon；2-(2-Phenylacetyl)cyclohexan-1-one
• CAS: 53661-37-3
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: QLZUNCACHLUBOH-UHFFFAOYSA-N

物化性质

• 沸点：
  95-105 °C(Press: 0.01 Torr)
• 密度：
  1.109±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-phenylacetyl)cyclohexanone 在 sodium tetrahydroborate 、 sodium dichromate 、 硫酸 、 三氯化铁 、 对甲苯磺酸 、 potassium amide 、 silver(l) oxide 作用下， 以 四氢呋喃 、 甲醇 、 氨 、 溶剂黄146 、 苯 为溶剂， 反应 24.5h， 生成 1-Benzyl-3-methoxy-isoquinoline-4-carbonitrile
  参考文献：
  名称：

  Kasturi, Tirumalai Rangachar; Krishnan, Lalitha; Prasad, Ramanujam Srinivasa, Journal of the Chemical Society. Perkin transactions I, 1982, p. 63 - 68

  摘要：

  DOI：
• 作为产物：
  描述：

  6-(2-苯基乙炔基)-7-氧杂二环[4.1.0]庚烷 在 甲酸 作用下， 反应 0.5h， 以30%的产率得到2-(2-phenylacetyl)cyclohexanone
  参考文献：
  名称：

  Eichinger, Karl; Berbalk, Hans; Machat, Eduard, Journal of Chemical Research, Miniprint, 1983, # 7, p. 1625 - 1649

  摘要：

  DOI：

文献信息

• Regiochemistry of the Reaction of 2-Acylcyclohexanones with Trimethyl Orthoformate: A Convenient One-Pot Method to Obtain 7,7-Dimethoxy Alkanoate Methyl Esters
  作者：Marcos A. P. Martins、Giovani P. Bastos、Adilson P. Sinhorin、Alex F. C. Flores、Helio G. Bonacorso、Nilo Zanatta

  DOI：10.1055/s-1999-2725

  日期：1999.6

  The regiochemistry of the reaction of 2-acylcyclohexanones [containing 2-acyl groups, C(O)R, where R = Me, Et, CH2Ph, CF3, Ph and OMe] with trimethyl orthoformate to obtain the corresponding acetal derivative is reported. Compounds with R = alkyl groups showed to be convenient synthons for a one-pot method to obtain 7,7-dimethoxy alkanoate methyl esters under mild conditions. The results of the reaction of 2-acetylcyclopentanone, -heptanone and -octanone with trimethyl orthoformate are also reported.

  报道了2-酰基环己酮（含有2-酰基团，C(O)R，其中R = Me、Et、CH2Ph、CF3、Ph和OMe）与三甲氧基甲烷反应生成相应缩醛衍生物的区域化学结果。R为烷基的化合物被证明是温和条件下通过一步法便捷地获得7,7-二甲氧基烷酸甲酯的前体。同时，也报道了2-乙酰基环戊酮、庚酮和辛酮与三甲氧基甲烷反应的结果。
• Fragment based lead discovery of small molecule inhibitors for the EPHA4 receptor tyrosine kinase
  作者：Oscar P.J. van Linden、Carine Farenc、Willem H. Zoutman、Liesbeth Hameetman、Maikel Wijtmans、Rob Leurs、Cornelis P. Tensen、Gregg Siegal、Iwan J.P. de Esch

  DOI：10.1016/j.ejmech.2011.11.020

  日期：2012.1

  The in silico identification, optimization and crystallographic characterization of a 6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c]isoquinolin-1-amine scaffold as an inhibitor for the EPHA4 receptor tyrosine kinase is described. A database containing commercially available compounds was subjected to an in silico screening procedure which was focused on finding novel, EPHA4 hinge binding fragments. This resulted in the identification of 6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c]isoquinolin-1-amine derivatives as EPHA4 inhibitors. Hit exploration yielded a compound with 2 μM (IC(50)) affinity for the EPHA4 receptor tyrosine kinase domain. Soaking experiments into a crystal of the EPHA4 kinase domain gave a 2.11Å X-ray structure of the EPHA4 - inhibitor complex, which confirmed the binding mode of the scaffold as proposed by the initial in silico work. The results underscore the strength of fragment based in silico screening as a tool for the discovery of novel lead compounds as small molecule kinase inhibitors.
• Henecka, Justus Liebigs Annalen der Chemie, 1953, vol. 583, p. 110,126
  作者：Henecka

  DOI：——

  日期：——
• Sharanin, Yu. A.; Shestopalov, A. M.; Rodinovskaya, L. A., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 2225 - 2230
  作者：Sharanin, Yu. A.、Shestopalov, A. M.、Rodinovskaya, L. A.、Promonenkov, V. K.、Litvinov, V. P.

  DOI：——

  日期：——
• KASTURI, TIRUMALAI, RANGACHAR;KRISHNAN, LALITHA;PRASAD, RAMANUJAM, SRINIV+, J. CHEM. SOC. PERKIN. TRANS., 1982, N 1, 63-68
  作者：KASTURI, TIRUMALAI, RANGACHAR、KRISHNAN, LALITHA、PRASAD, RAMANUJAM, SRINIV+

  DOI：——

  日期：——