4-hydroxy-5,5-dimethyl-3,4-di-p-tolyl-2-cyclopenten-1-one | 1211543-40-6

• 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-5,5-dimethyl-3,4-di-p-tolyl-2-cyclopenten-1-one
• 英文别名: 4-Hydroxy-5,5-dimethyl-3,4-di-p-tolyl-2-cyclopenten-1-one；4-hydroxy-5,5-dimethyl-3,4-bis(4-methylphenyl)cyclopent-2-en-1-one
• CAS: 1211543-40-6
• 化学式: C₂₁H₂₂O₂
• 分子量: 306.404
• InChiKey: VUJGUDOXGRVKGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 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-5,5-dimethyl-3,4-di-p-tolyl-2-cyclopenten-1-one 在 盐酸 、 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醚 、 乙醇 、 水 为溶剂， 反应 174.0h， 生成 1,5,5-trimethyl-3,4-di-p-tolyl-1,3-cyclopentadiene
  参考文献：
  名称：

  Dynamic NMR and computational study of 5,5-dimethyl-3,4-di-p-tolyl-2-cylopenten-1-one

  摘要：

  The restricted rotation of p-tolyl moiety in 5,5-dimethyl-3,4-di-p-tolyl-2-cyclopenten-1-one was studied by variable temperature NMR spectroscopy at a temperature range of 218-368 K. A free rotation, in NMR time scale, was observed at temperatures higher than 368 K; while, the rotation froze below 248 K. From dynamic NMR analysis, the Arrhenius energy of activation ΔG‡ was calculated as 56.37 kJ mol(-1). The experimental results were confirmed by theoretical calculation using the density functional theory method B3LYP with basis sets, 6-31G and 6-31+G.

  DOI：

  10.1016/j.saa.2011.05.060
• 作为产物：
  描述：

  3-甲基-2-丁酮 、 4,4'-二甲基联苯甲酰 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 3.75h， 以85%的产率得到4-hydroxy-5,5-dimethyl-3,4-di-p-tolyl-2-cyclopenten-1-one
  参考文献：
  名称：

  某些环戊烯酮的合成和4-羟基-3,4-双（4-甲氧基苯基）-5,5-二甲基-2-环戊烯-1-一的晶体结构

  摘要：

  摘要钠-氢氧化钠催化的二-缩合p甲基和二- p -methoxybenzil用丙酮衍生物在甲醇中的影响。获得二取代和三取代的产物为环戊烯酮，而四芳基取代的系统被分离为环戊二烯酮。产品的结构通过元素分析，红外（IR），核磁共振（1 H NMR）和质谱鉴定。通过单晶X射线衍射分析进一步研究了4-羟基-3,4-双（4-甲氧基苯基）-5,5-二甲基-2-环戊烯-1-酮的固态结构。标题化合物在正交晶空间群中结晶，并且分子间的OH-··O和CHH···O氢键稳定晶格。 图形概要

  DOI：

  10.1007/s00706-009-0177-8

文献信息

• Synthesis of some cyclopentenones and crystal structure of 4-hydroxy-3,4-bis(4-methoxyphenyl)-5,5-dimethyl-2-cyclopenten-1-one
  作者：Katayoun Marjani、Mohsen Mousavi、Omid Arazi、Akram Ashouri、Samira Bourghani、Mohammad Rajabi

  DOI：10.1007/s00706-009-0177-8

  日期：2009.11

  investigated in methanol. Di- and trisubstituted products were obtained as cyclopentenones, while tetraaryl-substituted systems were isolated as cyclopentadienones. The structures of the products were identified by elemental analysis, infrared (IR), nuclear magnetic resonance (1H NMR), and mass spectroscopy. The solid-state structure of 4-hydroxy-3,4-bis(4-methoxyphenyl)-5,5-dimethyl-2-cyclopenten-1-one

  摘要钠-氢氧化钠催化的二-缩合p甲基和二- p -methoxybenzil用丙酮衍生物在甲醇中的影响。获得二取代和三取代的产物为环戊烯酮，而四芳基取代的系统被分离为环戊二烯酮。产品的结构通过元素分析，红外（IR），核磁共振（1 H NMR）和质谱鉴定。通过单晶X射线衍射分析进一步研究了4-羟基-3,4-双（4-甲氧基苯基）-5,5-二甲基-2-环戊烯-1-酮的固态结构。标题化合物在正交晶空间群中结晶，并且分子间的OH-··O和CHH···O氢键稳定晶格。 图形概要
• Dynamic NMR and computational study of 5,5-dimethyl-3,4-di-p-tolyl-2-cylopenten-1-one
  作者：Katayoun Marjani、Mohsen Mousavi、Hossein Taherpour Nahzomi、Omid Arazi、Reza Jafari

  DOI：10.1016/j.saa.2011.05.060

  日期：2011.9

  The restricted rotation of p-tolyl moiety in 5,5-dimethyl-3,4-di-p-tolyl-2-cyclopenten-1-one was studied by variable temperature NMR spectroscopy at a temperature range of 218-368 K. A free rotation, in NMR time scale, was observed at temperatures higher than 368 K; while, the rotation froze below 248 K. From dynamic NMR analysis, the Arrhenius energy of activation ΔG‡ was calculated as 56.37 kJ mol(-1). The experimental results were confirmed by theoretical calculation using the density functional theory method B3LYP with basis sets, 6-31G and 6-31+G.