1-(3,4,5-三甲氧基苯基)-1,3-丁二酮 | 100613-36-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(3,4,5-三甲氧基苯基)-1,3-丁二酮
• 英文名称: 1-(3,4,5-trimethoxyphenyl)butane-1,3-dione
• 英文别名: 1-(3,4,5-trimethoxyphenyl)butan-1,3-dione；1-(3,4,5-trimethoxy-phenyl)-butane-1,3-dione；1-(3,4,5-Trimethoxy-phenyl)-butan-1,3-dion
• CAS: 100613-36-3
• 化学式: C₁₃H₁₆O₅
• 分子量: 252.267
• InChiKey: RLECIGKIHMADPU-UHFFFAOYSA-N

物化性质

• 沸点：
  370.8±37.0 °C(Predicted)
• 密度：
  1.130±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(3,4,5-三甲氧基苯基)-1,3-丁二酮 在 溴 作用下， 以 氯仿 、 丙酮 为溶剂， 反应 48.0h， 生成 2-(5,6-Dihydro-imidazo[2,1-b]thiazol-3-yl)-1-(3,4,5-trimethoxy-phenyl)-ethanone; hydrobromide
  参考文献：
  名称：

  Hablouj; Robert; Panouse, European Journal of Medicinal Chemistry, 1986, vol. 21, # 6, p. 499 - 504

  摘要：

  DOI：
• 作为产物：
  描述：

  α-(3,4,5-trimethoxyphenyl)-α-morpholinoacetonitrile 在 sodium hydride 、 copper(II) sulfate 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.5h， 生成 1-(3,4,5-三甲氧基苯基)-1,3-丁二酮
  参考文献：
  名称：

  Propargyl Bromide as an Excellent α-Bromoacetone Equivalent:  Convenient and New Route to α-Aroylacetones

  摘要：

  A variety of alpha-aroylacetones 4a-g have been prepared in excellent yields following a new protocol wherein alpha-aminonitriles la-g as the aryl acyl anion equivalents readily react with propargyl bromide as the alpha-bromoacetone equivalent. The alkylated product undergoes one-pot unmasking of the keto functionality along with Markovnikov's hydration of the terminal alkyne with CuSO(4)center dot 5H(2)O in aqueous methanol at 60 degrees C to furnish the desired target in excellent isolated yields.

  DOI：

  10.1021/jo051538w

文献信息

• Synthesis and Biological Evaluation of 3-Alkyl-1,5-Diaryl-1H-Pyrazoles as Rigid Analogues of Combretastatin A-4 with Potent Antiproliferative Activity
  作者：Qile Xu、Huan Qi、Maolin Sun、Daiying Zuo、Xuewei Jiang、Zhiyong Wen、Zhiwei Wang、Yingliang Wu、Weige Zhang

  DOI：10.1371/journal.pone.0128710

  日期：——

  A series of novel 3-alkyl-1,5-diaryl-1H-pyrazoles were synthesized as combretastatin A-4 (CA-4) analogues and evaluated for antiproliferative activity against three human cancer cell lines (SGC-7901, A549 and HT-1080). Most of the target compounds displayed moderate to potent antiproliferative activity, and 7k was found to be the most potent compound. Structure-activity relationships indicated that

  合成了一系列新型的3-烷基-1,5-二芳基-1H-吡唑类化合物，作为康布雷他汀A-4（CA-4）类似物，并评估了其对三种人类癌细胞系（SGC-7901，A549和HT- 1080）。大多数目标化合物都显示出中等至有效的抗增殖活性，而7k是最有效的化合物。构效关系表明，在吡唑骨架的N-1位带有三甲氧基苯基A环的化合物比在C-5位带有A环的化合物更有效。微管蛋白聚合和免疫染色实验表明，7k以类似于CA-4的方式有效抑制微管蛋白聚合并破坏微管蛋白微管动力学。
• Rhodium-Catalyzed Regioselective and Chemoselective Deoxygenative Reduction of 1,3-Diketones
  作者：Bing Zhang、Xueying Guo、Lei Tao、Ruolin Li、Zhenyang Lin、Wanxiang Zhao

  DOI：10.1021/acscatal.2c00520

  日期：2022.4.15

  aliphatic carbonyl reduction over aromatic carbonyl reduction. Moreover, the reaction showed good functional group tolerance and broad substrate scope as well as great potential in the late-stage modification and synthesis of natural products and pharmaceutical skeletons. Preliminary mechanistic studies and DFT calculations revealed that this reaction involved the deoxygenation of 1,3-diketone to α, β-unsaturated

  羰基化合物的脱氧还原已得到充分证实。然而，开发的大多数协议通常需要苛刻的反应条件或高反应性/毒性试剂，尽管 1,3-二酮对合成化学和材料科学很重要，但很少探索其脱氧还原。我们在这里描述了在温和反应条件下铑催化的区域选择性和化学选择性脱氧还原 1,3-二酮。与芳香族羰基还原相比，该方法对脂肪族羰基还原表现出异常高的区域选择性。此外，该反应还表现出良好的官能团耐受性和广泛的底物范围，在天然产物和药物骨架的后期修饰和合成中具有巨大潜力。初步机理研究和 DFT 计算表明，该反应涉及 1,3-二酮脱氧为 α, β-不饱和酮及其随后的 1,4-还原。与芳族 C=O 插入相比，脂肪族 C=O 插入 [Rh]-Bpin 的能垒明显较低，这是该还原过程中高区域选择性的原因。
• Photoredox-catalyzed 1,2-oxo-alkylation of vinyl arenes with 1,3-diketones: an approach to 1,4-dicarbonyls <i>via</i> C–C activation
  作者：Pushbaraj Palani、Ajithkumar Arumugam、Dineshkumar Raja、Kesavan Muthu、Gopal Chandru Senadi

  DOI：10.1039/d3cc02366d

  日期：——

  A mild approach to 1,4-diketones in moderate to excellent yields via 1,2-oxo alkylation has been developed using visible-light photocatalysis. The notable feature is the late-stage functionalization of thymol and ibuprofen derivatives.

  我们利用可见光光催化技术开发出了一种温和的方法，通过 1,2-oxo 烷基化反应以中等至极好的收率获得 1,4-二酮。其显著特点是百里酚和布洛芬衍生物的后期官能化。
• Aged red wine pigments as a source of inspiration for organic synthesis—the cases of the color-stable pyranoflavylium and flavylium-(4→8)-flavan chromophores
  作者：Stefan Chassaing、Géraldine Isorez-Mahler、Marie Kueny-Stotz、Raymond Brouillard

  DOI：10.1016/j.tet.2014.10.058

  日期：2015.5

  Two flavylium-based chromophores peculiar to aged red wine pigments are investigated from a synthetic viewpoint. The condensation between easy-to-prepare 5-hydroxy-4-methylflavylium salts and aldehydes, giving birth to color-stable pyranoflavylium pigments, further proves efficient and wide in scope. A set of some twenty structurally-related flavylium-based pigments has been prepared and structure:color relationships are discussed. Furthermore, the synthesis of the flavylium-(4 -> 8)-flavan chromophore is achieved via a novel three-step sequence. The elaborated sequence starts with an iodine magnesium exchange from an 8-iodinated flavan, thus generating a magnesiated species that then smoothly reacts with a flavone to furnish an adduct, that finally leads to the expected chromophore via dehydration. (C) 2014 Elsevier Ltd. All rights reserved.
• Regioselective synthesis of 6-aryl-5-(chloroethyl)salicylates by domino ‘[3+3] cyclization/homo-Michael’ reactions of 1,3-bis(silyloxy)-1,3-butadienes with 1-formyl- and 1-acetyl-1-aroyl-cyclopropanes
  作者：Abdolmajid Riahi、Matthias Lau、Helmut Reinke、Christine Fischer、Peter Langer

  DOI：10.1016/j.tet.2009.04.019

  日期：2009.7

  Functionalized 3-aryl-4-(chloroethyl)phenols are regioselectively prepared by domino '[3+3] cyclization/homo-Michael' reactions of 1,3-bis(silyloxy)-1,3-butadienes with 1-formyl- and 1-acetyl-1-aroyl-cyclopropanes. (C) 2009 Elsevier Ltd. All rights reserved.