1-(4-methoxyphenyl)-1,3-hexanedione | 791064-82-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-methoxyphenyl)-1,3-hexanedione
• 英文别名: 1-(4-Methoxyphenyl)hexane-1,3-dione
• CAS: 791064-82-9
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: BMLLVRZVNKJPQY-UHFFFAOYSA-N

物化性质

• 沸点：
  355.1±17.0 °C(Predicted)
• 密度：
  1.058±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 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：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-methoxyphenyl)-1,3-hexanedione 在 甲酸铵 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Direct Oxidative Coupling of Enamines and Electron-Deficient Amines: TBAI/TBHP-Mediated Synthesis of Substituted Diaminoalkenes under Metal-Free Conditions

  摘要：

  A metal-free cross-coupling of enamines and electron-deficient amines through oxidative C(sp(2))-N bond formation has been realized by using TBAI as catalyst and TBHP as oxidant. This novel strategy allows for an efficient organocatalytic synthesis of the synthetically useful diaminoalkene derivatives and is highlighted by appealing features such as readily available of the starting materials, wide substrate scope and transition-metal-free characteristics.

  DOI：

  10.1021/ol5026525
• 作为产物：
  描述：

  丁酸乙酯 、 对甲氧基苯乙酮 在 sodium 作用下， 反应 1.0h， 生成 1-(4-methoxyphenyl)-1,3-hexanedione
  参考文献：
  名称：

  作为康布雷他汀A-4的刚性类似物的3-烷基-1,5-二芳基-1H-吡唑的合成及生物评价，具有较强的抗增殖活性。

  摘要：

  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。

  DOI：

  10.1371/journal.pone.0128710

文献信息

• α‐Addition of 1,3‐Dicarbonyl Compounds to Acetylenic Ketones Catalyzed by Triphenylphosphine
  作者：Song Xue、Qing‐Fa Zhou、Xiao‐Qi Zheng

  DOI：10.1080/00397910500278602

  日期：2005.12

  Abstract The present work describes a simple way of synthesizing multifunctional compounds by α‐addition of 1,3‐dicarbonyl compounds to acetylenic ketones catalyzed by triphenylphosphine in moderate to good yields.

  摘要 目前的工作描述了一种通过 1,3-二羰基化合物与由三苯基膦催化的炔酮的 α-加成以中等至良好产率合成多功能化合物的简单方法。
• Formation of Functionalized 2<i>H</i>-Azirines through PhIO-Mediated Trifluoroethoxylation and Azirination of Enamines
  作者：Xiaoqian Sun、Youran Lyu、Daisy Zhang-Negrerie、Yunfei Du、Kang Zhao

  DOI：10.1021/ol4030716

  日期：2013.12.20

  A variety of enaminones and enamine carboxylic esters were converted to trifluoroethoxylated 2H-azirines through reactions with PhIO in trifluoroethanol (TFE). The cascade reaction is postulated to proceed via a PhIO-mediated oxidative trifluoroethoxylation and a subsequent azirination of the alpha-trifluoroethoxylated enamine intermediates.
• Iodobenzene Dichloride Mediated Sequential C–Cl Bond Formation: A Safe, Convenient and Efficient Method for the Direct α,α-Dichlorination of β-Dicarbonyl Compounds
  作者：Xiyan Duan、Junying Ma、Huiyun Zhou、Xinlei Tian、Jianwei Liu

  DOI：10.1055/s-0034-1379973

  日期：——

  Various -keto esters, 1,3-diketones, and -oxo amides are directly converted into their corresponding ,-dichloro--keto esters, 2,2-dichloro-1,3-diketones, and ,-dichloro--oxo amides, respectively, in moderate to high yields, using iodobenzene dichloride in dichloromethane in the presence of 4 angstrom molecular sieves at room temperature. This process is postulated to proceed via the iodobenzene dichloride mediated sequential oxidative -chlorination of the -dicarbonyl substrates.
• Modified reaction conditions to achieve high regioselectivity in the two component synthesis of 1,5-diarylpyrazoles
  作者：Sunil K. Singh、M. Srinivasa Reddy、S. Shivaramakrishna、D. Kavitha、R. Vasudev、J. Moses Babu、A. Sivalakshmidevi、Y. Koteswar Rao

  DOI：10.1016/j.tetlet.2004.08.100

  日期：2004.10

  The factors affecting regioselectivity during the formation of 1,5-diarylpyrazoles from aryl hydrazines and 1,3-diketones are identified and the regioisomers were characterized by 1D NOESY, LC-NMR and X-ray analyses. A simple alteration in the usual reaction conditions is reported, which allows the exclusive formation of 1,5-diarylpyrazoles. (C) 2004 Elsevier Ltd. All rights reserved.
• Zinc-Mediated Chain Extension Reaction of 1,3-Diketones to 1,4-Diketones and Diastereoselective Synthesis of <i>trans</i>-1,2-Disubstituted Cyclopropanols
  作者：Song Xue、Le-Zhen Li、Yong-Kang Liu、Qing-Xiang Guo

  DOI：10.1021/jo051950b

  日期：2006.1.1

  A variety of 1,3-diketones can be efficiently converted into the corresponding 1.4-diketones and trans-1,2-disubstituted cyclopropanols by using organozinc species in one-pot reactions. It was found that 2.3 equiv of CF3CO2ZnCH2I was effective to give the corresponding chain-extended products in 44-85% yields, while a mixture of organozinc species formed from 4.0 equiv of Et2Zn, 2.0 equiv of CF3CO2H, and 4.0 equiv of CH2I2 resulted in the formation of trans-1,2-disubstituted cyclopropanols with quite good yields and diastereoselectivity.