di(3-methylbenzylidene)acetone | 17011-56-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: di(3-methylbenzylidene)acetone
• 英文别名: 1,5-Bis-(m-tolyl)-1,4-pentadien-3-on；1,5-Bis(3-methylphenyl)-1,4-pentadien-3-one；1,5-bis(3-methylphenyl)penta-1,4-dien-3-one
• CAS: 17011-56-2
• 化学式: C₁₉H₁₈O
• 分子量: 262.351
• InChiKey: KLSUMXUEVAJVLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  di(3-methylbenzylidene)acetone 在 盐酸 、 三氟化硼乙醚 、 sodium acetate 作用下， 以 四氢呋喃 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.83h， 生成 3,3'-(4-(trifluoromethyl)cyclopenta-1,3-diene-1,2-diyl)bis(methylbenzene)
  参考文献：
  名称：

  Efficient synthesis of trifluoromethylated cyclopentadienes/fulvenes/norbornenes from divinyl ketones

  摘要：

  已开发出合成三氟甲基化环戊二烯/富烯/诺尔博烯的方法，使用3-CF3-1,4-二烯-3-醇作为合成前体，这些前体可以通过Ruppert–Prakash试剂（TMSCF3）与二烯酮进行 regio-specific 1,2-加成轻松制备。所有反应均在温和的无金属条件下进行，产物得率高至优秀。

  DOI：

  10.1039/c3ob41400k
• 作为产物：
  描述：

  异丙醇 、 3-甲基苯甲醛 在 Wilkinson's catalyst 、 三氟化硼乙醚 作用下， 以 甲苯 为溶剂， 以76%的产率得到di(3-methylbenzylidene)acetone
  参考文献：
  名称：

  A RhCl(PPh3)3/BF3·OEt2 co-promoted direct C–C cross-coupling of alcohols at β-position with aldehydes

  摘要：

  A novel RhCl(PPh3)(3)/BF3 center dot OEt2 co-promoted direct C-C cross-coupling of primary and secondary alcohols at beta-position with aldehyde was developed. This reaction could provide an efficient synthesis of a series of alpha, beta-unsaturated aldehydes and diarylidene ketones, just from simple and easily available alcohols and aldehydes. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.05.006

文献信息

• Chemoselective Double Michael Addition: Synthesis of 2,6-Diarylspiro[Cyclohexane-1,3′-Indoline]-2′,4-Diones via Addition of Indolin-2-One to Divinyl Ketones
  作者：Zheng Li、Jiasheng Li、Jingya Yang

  DOI：10.3184/174751917x14878812592779

  日期：2017.3

  Seventeen examples of 2,6-diarylspiro[cyclohexane-1,3′-indoline]-2′4-diones were efficiently prepared by the Cs₂CO₃-catalysed chemoselective double Michael additions of indolin-2-one to divinyl ketones. This method has the advantage of high chemoselectivity, mild reaction conditions, high yield and atom- and step-economy.

  通过 Cs2CO3 催化吲哚啉-2-酮与二乙烯基酮的化学选择性双迈克尔加成反应，有效地制备了 17 个 2,6-二芳基螺[环己烷-1,3′-吲哚啉]-2′4-二酮的实例。该方法具有化学选择性高、反应条件温和、产率高、原子和步骤经济等优点。
• Synthesis of 4-arylethyl-6-arylpyrimidine-2-thiols through aza-Michael addition/nucleophilic addition/aromatization tandem reactions
  作者：Zheng Li、Wenli Song、Jiaojiao He、Yan Du、Jingya Yang

  DOI：10.1515/hc-2017-0169

  日期：2018.2.23

  Abstract An efficient method for the synthesis of the title compounds by reactions of divinyl ketones with thiourea is described. This protocol has the advantages of high yields, mild reaction conditions and simple work-up procedure.

  摘要 描述了一种通过二乙烯基酮与硫脲反应合成标题化合物的有效方法。该方案具有收率高、反应条件温和、后处理程序简单等优点。
• A highly organocatalytic stereoselective double Michael reaction: efficient construction of optically enriched spirocyclic oxindoles
  作者：Liang-Liang Wang、Lin Peng、Jian-Fei Bai、Li-Na Jia、Xi-Ya Luo、Qing-Chun Huang、Xiao-Ying Xu、Li-Xin Wang

  DOI：10.1039/c1cc11223f

  日期：——

  An array of spirocyclic oxindoles have been constructed via a double Michael reaction in high yields and excellent enantioselectivities.

  一系列螺环氧吲哚化合物已经通过双Michael反应高产率和优异对映选择性构建。
• Synthesis of tetrasubstituted 1H-indazolo[1,2-b]phthalazinedione derivatives bearing three-dimensional turbine-type structures via domino reaction of phthalhydrazide and vinylketones
  作者：Ya-Lun Xu、Ji-Ya Fu、Chun-Hui Liu、Tao Ding

  DOI：10.1039/c7ra06856e

  日期：——

  A domino reaction of phthalhydrazide and vinylketone in the presence of phosphotungstic acid was successfully established, and 3D turbine-type tetrasubstituted 1H-indazolo[1,2-b]phthalazinedione derivatives were conveniently obtained with moderate to excellent yields (up to 95%). The highly efficient catalytic system exhibited broad substrate scopes under mild conditions. A 78% yield of the desired

  成功地建立了在磷钨酸存在下的邻苯二甲酰肼和乙烯基酮的多米诺反应，并以中等至优异的收率（高达95％）方便地获得了3D涡轮型四取代的1 H-吲哚并[1,2- b ]酞嗪二酮衍生物。 。高效的催化体系在温和的条件下具有广阔的底物范围。当反应在几克规模下进行时，获得了所需产物的78％的收率。
• Synthesis of Optically Enriched Spirocyclic Benzofuran-2-ones by Bifunctional Thiourea-Base Catalyzed Double-Michael Addition of Benzofuran-2-ones to Dienones
  作者：Xin Li、Chen Yang、Jia-Lu Jin、Xiao-Song Xue、Jin-Pei Cheng

  DOI：10.1002/asia.201201244

  日期：2013.5

  A highly enantioselective catalytic double‐Michael addition reaction of substituted benzofuran‐2‐ones with divinyl ketones promoted by readily accessible tertiary amine–thiourea Cinchona alkaloids has been developed. A number of optically enriched spirocyclic benzofuran‐2‐ones were prepared in very good yields (up to 99 %), diastereoselectivities (up to 19:1 d.r.), and very good enantioselectivities

  已经开发出一种高度对映选择性的双苯甲酰呋喃-2-酮催化的双迈克尔加成反应与易于获得的叔胺-硫脲金鸡纳生物碱促进的二乙烯基酮。制备了许多光学富集的螺环苯并呋喃-2-酮，具有很高的收率（高达99％），非对映选择性（高达19：1 dr）和非常好的对映选择性（高达92％ee）。进行密度泛函理论（DFT）计算以研究立体选择性的起源。