(4S,5R)-4-hydroxy-2,5-dimethyl-3,4-diphenylcyclopent-2-en-1-one | 5423-06-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (4S,5R)-4-hydroxy-2,5-dimethyl-3,4-diphenylcyclopent-2-en-1-one
• 英文别名: (+/-)-4r-hydroxy-2,5t-dimethyl-3,4-diphenyl-cyclopent-2-enone；(+/-)-4r-Hydroxy-2,5t-dimethyl-3,4-diphenyl-cyclopent-2-enon；(4R,5S)-4-hydroxy-2,5-dimethyl-3,4-diphenylcyclopent-2-en-1-one
• CAS: 5423-06-3；38661-95-9；38661-96-0；52956-59-9；53159-99-2
• 化学式: C₁₉H₁₈O₂
• 分子量: 278.351
• InChiKey: VAAQGIJITBVELH-AUUYWEPGSA-N

物化性质

• 熔点：
  152-153 °C(Solv: methanol (67-56-1))
• 沸点：
  381.4±42.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2914400090

反应信息

• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氢氧化钾 作用下， 生成 (4S,5R)-4-hydroxy-2,5-dimethyl-3,4-diphenylcyclopent-2-en-1-one
  参考文献：
  名称：

  Condensation of aliphatic ketones with benzil

  摘要：

  DOI：

  10.1021/jo00949a033

文献信息

• Preparation of cyclopentadienes and diazocyclopentadienesvia cyclopentenolones and cyclopentenones
  作者：B.H. Freeman、J.M.F. Gagan、D. Lloyd

  DOI：10.1016/0040-4020(73)80276-5

  日期：1973.12

  The structure and stereochemistry of the cyclopentenolones obtained by condensation of dialkyl ketones with benzil have been studied by NMR spectroscopy. These enolones were converted into cyclopentenones and cyclopentadienes. Alkyl-substituted cyclopentadienes required phenyllithium to effect their conversion by toluenesulphonyl azide into diazo-cyclopentadienes; otherwise piperidine sufficed as base

  通过NMR光谱研究了通过二烷基酮与苯甲酰缩合获得的环戊烯酮的结构和立体化学。这些烯醇酮被转化为环戊烯酮和环戊二烯。烷基取代的环戊二烯需要苯基锂才能通过甲苯磺酰叠氮化物将其转化为重氮-环戊二烯；简单地通过使苯甲酰和苯丙酮的缩合产物与甲苯磺酰基alkali反应，然后使碱反应来制备2,3,4-三苯基重氮环戊二烯。通过分别在环己烷或甲醇中光分解重氮三苯基环戊二烯来制备环己基-和甲氧基-三苯基环戊二烯。
• Structure of 2(5)-alkyl-4-hydroxy-3,4-diphenylcyclopent-2-en-1-ones, cyclocondensation products of benzil with aliphatic ketones
  作者：I. V. Mikhura、A. A. Formanovskii、A. S. Shashkov

  DOI：10.1134/s1070428010080026

  日期：2010.8

  The reaction of benzil with methyl alkyl ketones gave three isomeric cyclopentenone derivatives, 2-substituted and cis- and trans-5-substituted 4-hydroxy-3,4-diphenylcyclopent-2-en-1-ones. cis- and trans-2,5-Disubstituted 4-hydroxy-3,4-diphenylcyclopent-2-en-1-ones were formed in analogous reaction of benzil with dialkyl ketones. The structure of the products was confirmed by (1)H NMR spectroscopy and molecular-mechanics calculations.