2-(4-Chloro-phenyl)-4-hydroxy-4-methyl-6-oxo-cyclohexane-1,3-dicarboxylic acid diethyl ester | 294194-13-1

• 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: 2-(4-Chloro-phenyl)-4-hydroxy-4-methyl-6-oxo-cyclohexane-1,3-dicarboxylic acid diethyl ester
• 英文别名: diethyl 2-(4-chlorophenyl)-4-hydroxy-4-methyl-6-oxocyclohexane-1,3-dicarboxylate；2-(4-Chlor-phenyl)-4-hydroxy-4-methyl-6-oxo-cyclohexan-1,3-dicarbonsaeure-diaethylester；1-Methyl-3-(4-chlor-phenyl)-cyclohexanol-(1)-on-(5)-dicarbonsaeure-(2.4)-diaethylester
• CAS: 294194-13-1
• 化学式: C₁₉H₂₃ClO₆
• mdl: MFCD00370610
• 分子量: 382.841
• InChiKey: SNYBQIIVGREIAE-UHFFFAOYSA-N

物化性质

• 沸点：
  505.6±50.0 °C(Predicted)
• 密度：
  1.264±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  2-(4-Chloro-phenyl)-4-hydroxy-4-methyl-6-oxo-cyclohexane-1,3-dicarboxylic acid diethyl ester 在 氢氧化钾 作用下， 生成 5-(4-chlorophenyl)-3-methylcyclohex-2-enone
  参考文献：
  名称：

  Knoevenagel, Justus Liebigs Annalen der Chemie, 1898, vol. 303, p. 255

  摘要：

  DOI：
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 4-氯苯甲醛 在 哌啶 作用下， 以 乙醇 为溶剂， 以69%的产率得到2-(4-Chloro-phenyl)-4-hydroxy-4-methyl-6-oxo-cyclohexane-1,3-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  通过芳族醛与β-酮酸酯或酮的顺序反应有效地选择性合成官能化联苯

  摘要：

  芳族醛和β-酮酯/酮的Knoevenagel / Michael / Aldol反应以连续的方式以良好的收率得到中间体环己酮。后者在用碘进行氧化芳构化后，以中等至良好的产率获得了具有至少一个酚羟基的官能化联苯。

  DOI：

  10.1016/j.tetlet.2009.02.001

文献信息

• An efficient regioselective synthesis of functionalized biphenyls via sequential reactions of aromatic aldehydes and β-keto esters or ketones
  作者：Anindra Sharma、Jyoti Pandey、R.P. Tripathi

  DOI：10.1016/j.tetlet.2009.02.001

  日期：2009.4

  Knoevenagel/Michael/Aldol reactions of aromatic aldehydes and β-keto esters/ketones in a sequential manner yielded intermediate cyclohexanones in good yields. The latter, on oxidative aromatization with iodine, afforded functionalized biphenyls with at least one phenolic hydroxyl in moderate to good yields.

  芳族醛和β-酮酯/酮的Knoevenagel / Michael / Aldol反应以连续的方式以良好的收率得到中间体环己酮。后者在用碘进行氧化芳构化后，以中等至良好的产率获得了具有至少一个酚羟基的官能化联苯。
• 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 ，
• Rabe; Elze, Justus Liebigs Annalen der Chemie, 1902, vol. 323, p. 94
  作者：Rabe、Elze

  DOI：——

  日期：——
• Catalysis by Amberlyst A-21: A Greener Approach to 4,5,6,7-Tetrahydro-1H-indazol-3(2<i>H</i>)-ones via Construction of Cyclohexanones
  作者：Manam Sreenivasa Rao、Meda Haritha、Sunder Kumar Kolli、Mandava V. Basaveswara Rao、Manojit Pal

  DOI：10.1080/00397911.2013.844260

  日期：2014.4.18

  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.]