4-hydroxy-2-methyl-3,4-diphenylcyclopent-2-enone | 38661-97-1

• 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: 4-hydroxy-2-methyl-3,4-diphenylcyclopent-2-enone
• 英文别名: 4-hydroxy-2-methyl-3,4-diphenylcyclopent-2-en-1-one；4-Hydroxy-2-methyl-3,4-diphenyl-cyclopent-2-enon
• CAS: 38661-97-1
• 化学式: C₁₈H₁₆O₂
• 分子量: 264.324
• InChiKey: QHTSZFGLTOSSQJ-UHFFFAOYSA-N

物化性质

• 熔点：
  114-116 °C
• 沸点：
  374.0±42.0 °C(Predicted)
• 密度：
  1.210±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-hydroxy-2-methyl-3,4-diphenylcyclopent-2-enone 在 sodium tetrahydroborate 、 magnesium sulfate 作用下， 反应 0.12h， 以95%的产率得到(1S,3R)-4-methyl-1,5-diphenylcyclopent-4-ene-1,3-diol
  参考文献：
  名称：

  Microwave-Assisted Reduction of α,β-Unsaturated Carbonyl Compounds in Solid State Using Sodium Borohydide Supported on Magnesium Sulfate (NaBH₄/MgSO₄-7H₂O)

  摘要：

  Reduction of varieties of carbonyl compounds such as ketones and alpha,beta-unsaturated cyclic ketones were carried out quickly and efficiently by NaBH4/MgSO4-7H(2)O under microwave irradiation. The corresponding products were obtained in high to excellent yields.

  DOI：

  10.1080/00397910802149097
• 作为产物：
  描述：

  联苯甲酰 、 丁酮 在 氢氧化钾 作用下， 生成 4-hydroxy-2-methyl-3,4-diphenylcyclopent-2-enone
  参考文献：
  名称：

  通过环戊烯酮和环戊烯酮制备环戊二烯和重氮环戊二烯

  摘要：

  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。

  DOI：

  10.1016/0040-4020(73)80276-5

文献信息

• Synthesis of New Pyrazoles via Cycloaddition Reactions of Nitrilimines with 2-Cyclopentenone Derivatives
  作者：Fatma A. El-Samahy

  DOI：10.1002/jhet.2077

  日期：2015.3

  4‐tetraphenyl‐1,3a‐dihydrocyclopenta[c]pyrazol‐6‐ols (4) and 6‐hydroxy‐1,3,6,6a‐tetraphenyl‐1,5,6,6a‐tetrahydrocyclopenta[c]pyrazole‐4(aH)‐one (5) were synthesized by reaction of 3,4‐diphenyl‐4‐hydroxy‐2‐cyclopentenone (2a) with nitrilimines, generated in situ by the action of triethylamine on the corresponding hydrazonyl chlorides 1.

  化合物1,3,6,6a-四苯基-1,6a-二氢环戊五[ c ]吡唑-4（3a H）-ones（3），1,3,3a，4-四苯基-1,3a-二氢环戊五[c]吡唑-6-醇（4）和6-羟基-1,3,6,6a-四苯基-1,5,6,6a-四氢环戊[ c ]吡唑-4（a H）-one（5）的合成3,4-二苯基-4-羟基-2-环戊烯酮（2a）与亚硝胺的反应，该反应由三乙胺在相应的酰肼基氯的作用下原位产生1。
• Japp; Meldrum, Journal of the Chemical Society, 1901, vol. 79, p. 1033
  作者：Japp、Meldrum

  DOI：——

  日期：——
• 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.
• Gray, Journal of the Chemical Society, 1909, vol. 95, p. 2148
  作者：Gray

  DOI：——

  日期：——
• EVIDENCE FOR THE PRESENCE OF AN ANGULAR PHENYL GROUP IN THE BIMOLECULAR PRODUCT FROM METHYL-ANHYDROACETONEBENZIL
  作者：C. F. H. ALLEN、J. VanALLAN

  DOI：10.1021/jo01180a012

  日期：1945.7