3-(p-methylphenyl)-2,4-dicarboethoxy-5-hydroxy-5-methylcyclohexanone | 79988-72-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(p-methylphenyl)-2,4-dicarboethoxy-5-hydroxy-5-methylcyclohexanone
• 英文别名: diethyl 4-hydroxy-4-methyl-2-(4-methylphenyl)-6-oxocyclohexane-1,3-dicarboxylate；diethyl 4-hydroxy-4-methyl-6-oxo-2-(p-tolyl)cyclohexane-1,3-dicarboxylate；4-hydroxy-4-methyl-6-oxo-2-p-tolyl-cyclohexane-1,3-dicarboxylic acid diethyl ester；4-Hydroxy-4-methyl-6-oxo-2-p-tolyl-cyclohexan-1,3-dicarbonsaeure-diaethylester
• CAS: 79988-72-0
• 化学式: C₂₀H₂₆O₆
• 分子量: 362.423
• InChiKey: ONOVZUNPHDZFBJ-UHFFFAOYSA-N

物化性质

• 熔点：
  129 °C(Solv: water (7732-18-5); methanol (67-56-1))
• 沸点：
  498.2±45.0 °C(Predicted)
• 密度：
  1.180±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(p-methylphenyl)-2,4-dicarboethoxy-5-hydroxy-5-methylcyclohexanone 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以81%的产率得到ethyl 6-hydroxy-6-methyl-3-oxo-4-p-tolyl-2,3,4,5,6,7-hexahydro-1H-indazole-5-carboxylate
  参考文献：
  名称：

  Catalysis by Amberlyst A-21: A Greener Approach to 4,5,6,7-Tetrahydro-1H-indazol-3(2H)-ones via Construction of Cyclohexanones

  摘要：

  The 4,5,6,7-tetrahydro-1H-indazol-3(2H)-one derivatives have been synthesized in good yields via a two-step method in a single pot. The initial step involved the construction of cyclohexanone ring from aromatic aldehydes and beta-ketoester in i-PrOH using an inexpensive and reusable catalyst (i.e., Amberlyst A-21) under mild reaction conditions. The utility of this catalyst has been demonstrated in synthesizing a range of cyclohexanone derivatives. The catalyst can be recovered and recycled, which makes this procedure simple, convenient, economically viable, and environmental friendly. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]

  DOI：

  10.1080/00397911.2013.844260
• 作为产物：
  描述：

  对甲基苯甲醛 、 乙酰乙酸乙酯 在 哌啶 作用下， 生成 3-(p-methylphenyl)-2,4-dicarboethoxy-5-hydroxy-5-methylcyclohexanone
  参考文献：
  名称：

  高度官能化的3,4-环己烷退火香豆素的合成

  摘要：

  通过结合两种方法，可以有效地合成高度官能化的3,4-环己烷退火香豆素。首先，通过将各种苯甲醛与乙酰乙酸乙酯缩合，可方便地制备重要的中间体多取代的环状β-酮酯。然后，通过Amberlyst-15催化的多取代环β-酮酯与酚的Pechmann缩合反应，合成了一系列高度官能化的3,4-环己烷-退火香豆素。该合成方法的优点是反应条件温和，对各种官能团的耐受性好，产率令人满意。

  DOI：

  10.1007/s11164-013-1212-2

文献信息

• Indion 860 catalyzed cascade reaction: a greener approach to functionalized cyclohexanones and their novel analogues
  作者：T. Bhaskar Kumar、G. Dhananjaya、Ch. Sumanth、S. Vaishaly、Gajanan Botre、M. Srinivasa Rao、K. B. Chandra Sekhar、K. Shiva Kumar、Manojit Pal

  DOI：10.1039/c2ra23039a

  日期：——

  An Indion 860 mediated cascade reaction of β-ketoester or 1,3-diketone with alkyl/aryl/heteroaryl aldehydes afforded functionalized cyclohexanones in the open air. The catalyst can be recovered and recycled. Combining this methodology with other reactions in the same pot afforded diversity based novel molecules. Some of the synthesized compounds showed inhibition of PDE4 in vitro.

  通过 Indion 860 介导的β-酮酯或 1,3-二酮与烷基/芳基/杂芳基醛的级联反应，可在露天条件下生成官能化环己酮。催化剂可以回收和循环使用。将这一方法与同一锅中的其他反应相结合，可以得到多种多样的新型分子。一些合成的化合物在体外显示出对 PDE4 的抑制作用。
• Syntheses and some features of five new cyclohexane-1,3-dicarboxylates with multiple stereogenic centers
  作者：Arif M. Ismiyev、Abel M. Maharramov、Rafiga A. Aliyeva、Rizvan K. Askerov、Kamran T. Mahmudov、Maximilian N. Kopylovich、Houcine Naïli、Armando J.L. Pombeiro

  DOI：10.1016/j.molstruc.2012.08.006

  日期：2013.1

  only cyclohexanone carbonyl moiety undergoes the transformation, leaving the β-keto ester carbonyls unreacted. Withing the compounds 1 – 5 , the increase in the Hammett’s σ p , related normal σ p n , inductive σ I , negative σ p - and positive σ p + polar conjugation and Taft’s σ p o substituent constants generally leads to the corresponding drift of δ O H and δ N H NMR chemical shifts to lower field

  摘要 4-羟基-4-甲基-6-氧代-2-(4-取代苯基)-环己烷-1,3-二羧酸二乙酯与N'-(2-氯丙基)乙烷-1,2-二胺缩合得到1-(2-氯丙基)-9-羟基-9-甲基-7-苯基-1,4-二氮杂螺[4.5]癸烷-6,8-二羧酸二乙酯(2)及其对位取代甲基(1)、氯( 3 )、溴 ( 4 ) 和硝基 ( 5 ) 衍生物具有新的立体中心，通过元素分析、ESI-MS、IR、 1 H 和 13 C NMR 光谱和 X 射线单晶分析进行了充分表征（对于 2 ）。缩合反应是区域选择性的，只有环己酮羰基部分发生转化，留下未反应的 β-酮酯羰基。对于化合物 1 – 5，哈米特的 σ p 增加，相关法向 σ pn ，归纳 σ I ，
• Synthesis of 6H-Dibenzo[b,d]pyran-6-one Derivatives via Coumarin-Fused Cyclohexa-1,3-diene Intermediates
  作者：Zhi-Zhen Huang、Chao-Yue Chen、Yong-Sheng Zhao、Chang-Bing Xiang

  DOI：10.1055/s-0031-1289810

  日期：2012.8

  In the presence of trifluoroacetic acid and methanesulfonic acid (MSA), a series of monohydric and polyhydric phenols readily undergo a domino Pechmann-dehydration reaction with various 4-hydroxy-6-oxocyclohexane-1,3-dicarboxylates to give 7,8-dihydro-6H-dibenzo[b,d]pyran-6-ones. Subsequent dehydrogenation of the 7,8-dihydro-6H-dibenzo[b,d]pyran-6-ones was performed expediently with DBU/BrCCl3 to give various 6H-dibenzo[b,d]pyran-6-one derivatives. This strategy has the advantages of inexpensive and easily available raw materials, metal-free procedure, mild reaction conditions, good compatibility with various functional groups, and satisfactory yields.
• Abbas Metwally; El-Hussiny; El-Ablak, Pharmazie, 1989, vol. 44, # 4, p. 261 - 265
  作者：Abbas Metwally、El-Hussiny、El-Ablak、Khalil

  DOI：——

  日期：——
• Metwally; El-Hossini; El-Ablak, Pharmazie, 1992, vol. 47, # 5, p. 336 - 339
  作者：Metwally、El-Hossini、El-Ablak、Khalil

  DOI：——

  日期：——