2,2'-(benzo[d][1,3]dioxol-5-ylmethylene)bis(3-hydroxy-5,5-dimethylcyclohex-2-enone)

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2,2'-(benzo[d][1,3]dioxol-5-ylmethylene)bis(3-hydroxy-5,5-dimethylcyclohex-2-enone)
• 英文别名: 2,2-(3,4-methylenedioxyphenyl)methylene bis(3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one)；2-[1,3-benzodioxol-5-yl-(2-hydroxy-4,4-dimethyl-6-oxocyclohexen-1-yl)methyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one
• 化学式: C₂₄H₂₈O₆
• 分子量: 412.483
• InChiKey: YFXLKVJEFRKWQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  胡椒醛 、 5,5-二甲基-1,3-环己二酮 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以81%的产率得到2,2'-(benzo[d][1,3]dioxol-5-ylmethylene)bis(3-hydroxy-5,5-dimethylcyclohex-2-enone)
  参考文献：
  名称：

  芳香醛与酸性亚甲基化合物的缩合反应

  摘要：

  摘要 芳醛与异亚丙基丙二酸酯或5,5-二甲基-1,3-环己二酮的缩合反应以DMF为溶剂，无催化剂。

  DOI：

  10.1080/00397910008087374

文献信息

• Organocatalytic Sequential One-Pot Double Cascade Asymmetric Synthesis of Wieland−Miescher Ketone Analogues from a Knoevenagel/Hydrogenation/Robinson Annulation Sequence:  Scope and Applications of Organocatalytic Biomimetic Reductions
  作者：Dhevalapally B. Ramachary、Mamillapalli Kishor

  DOI：10.1021/jo070277i

  日期：2007.7.1

  practical and novel organocatalytic chemo- and enantioselective process for the cascade synthesis of highly substituted 2-alkyl-cyclohexane-1,3-diones and Wieland−Miescher (W−M) ketone analogs is presented via reductive alkylation as a key step. First time, we developed the one-step alkylation of dimedone and 1,3-cyclohexanedione with aldehydes and Hantzsch ester through an organocatalytic reductive alkylation

  通过还原烷基化，提出了一种实用且新颖的有机催化化学和对映选择性工艺，用于级联合成高度取代的2-烷基-环己烷-1,3-二酮和Wieland-Miescher（WM）酮类似物，这是关键步骤。首次，我们通过有机催化还原烷基化策略开发了二醛和1,3-环己二酮与醛和Hantzsch酯的一步烷基化。l的直接组合CH酸（二甲酮和1,3-环己烷二酮），醛，汉茨sch酯和甲基乙烯基酮的脯氨酸催化的级联Knoevenagel /加氢和级联的Robinson环氧化反应提供了高官能度的W-M酮类似物，并具有良好的收率。优异的对映选择性。许多还原性烷基化产物直接显示在药物化学中。
• Evaluation of sodium acetate trihydrate–urea DES as a benign reaction media for the Biginelli reaction. Unexpected synthesis of methylenebis(3-hydroxy-5,5-dimethylcyclohex-2-enones), hexahydroxanthene-1,8-diones and hexahydroacridine-1,8-diones
  作者：Camilo A. Navarro、Cesar A. Sierra、Cristian Ochoa-Puentes

  DOI：10.1039/c6ra13848a

  日期：——

  In this work, the low melting mixture sodium acetate trihydrate–urea was synthesized and the eutectic composition was determined and characterized. The performance of this deep eutectic solvent on the Biginelli reaction was evaluated.

  在这项工作中，合成了低熔点混合物醋酸钠三水合物-尿素，并确定并表征了共熔组成。评估了这种深共熔溶剂在Biginelli反应中的性能。
• Chickpea leaf exudates (CLE) mediated Knoevenagel–Michael reactions for the synthesis of diketodiols and biscoumarins
  作者：Rupesh C. Patil、Dnyandev N. Zambare、Shashikant A. Damate、Ashutosh A. Jagdale、Snehali R. Mali、Sachinkumar K. Shinde、Suresh S. Patil

  DOI：10.1007/s11164-022-04707-8

  日期：2022.5

  A green, highly efficient, and eco-friendly protocol for Knoevenagel–Michael addition reaction is reported in Chickpea leaf exudates (CLE) as a naturally sourced biosurfactant. The reactions between dimedone/4-hydroxycoumarins and a variety of aryl aldehydes were carried out in presence of CLE to afford diketodiols/biscoumarins. The synthetic pathway complies with several key requirements of green chemistry principles such as the employment of natural feedstock as green reaction media, ambient temperature, atom economy along with natural biosurfactant type Bronsted acids, and recyclable and biodegradable catalyst which led to a 28-fold increase in molar efficiency versus industrial standard protocols. Its dynamic phase is confirmed by the optical microscopy technique and critical micelle concentration measurement. The notable advantages of the present protocol were simple work-up procedure, high yield within short reaction time, easy separation of products, avoiding tedious column chromatography thus making the protocol environmentally friendly, sustainable, and economical.

  报告采用鹰嘴豆叶渗出物（CLE）作为天然生物表面活性剂，提出了一种绿色、高效、环保的 Knoevenagel-Michael 加成反应方案。在 CLE 的存在下，二酮/4-羟基香豆素与多种芳基醛发生反应，生成二酮二醇/双香豆素。该合成途径符合绿色化学原则的几个关键要求，如使用天然原料作为绿色反应介质、环境温度、原子经济性以及天然生物表面活性剂型勃朗斯特酸和可回收和生物降解催化剂，与工业标准协议相比，摩尔效率提高了 28 倍。光学显微镜技术和临界胶束浓度测量证实了其动态阶段。本方案的显著优点是操作步骤简单，反应时间短，产率高，产品易于分离，避免了繁琐的柱层析，从而使该方案具有环境友好性、可持续性和经济性。
• Reaction of Imines with 5,5‐Dimethyl‐1, 3‐cyclohexandione
  作者：Liangce Rong、Xiaoyue Li、Haiying Wang、Daqing Shi、Shujiang Tu、Qiya Zhuang

  DOI：10.1080/00397910600640131

  日期：2006.8

  The reaction of imines 1 with 5,5-dimethyl-1,3-cyclohexandione 2 in methanol was investigated. When the reaction was carried out without a catalytic amount of molecular iodine, ring-opening derivatives of xanthenediones 3 were obtained in high yields. On the other hand, when molecular iodine and a catalytic amount of zinc powder were employed as the catalyst, xanthenediones derivatives 4 were obtained with excellent yields.
• Samanta, Swati; Das Gupta, Arpita; Mondal, Rina, Journal of the Indian Chemical Society, 2013, vol. 90, # 6, p. 845 - 852
  作者：Samanta, Swati、Das Gupta, Arpita、Mondal, Rina、Mallik, Asok Kumar

  DOI：——

  日期：——