2,2-dimethyl-5-((5-methylfuran-2-yl)methylene)-1,3-dioxane-4,6-dione | 109610-93-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-dimethyl-5-((5-methylfuran-2-yl)methylene)-1,3-dioxane-4,6-dione
• 英文别名: 2,2-dimethyl-5-(5-methyl-2-furfurylidene)-1,3-dioxane-4,6-dione；2,2-dimethyl-5-(5-methylfurfurylidene)-1,3-dioxane-4,6-dione；2,2-Dimethyl-5-[(5-methylfuran-2-yl)methylidene]-1,3-dioxane-4,6-dione
• CAS: 109610-93-7
• 化学式: C₁₂H₁₂O₅
• mdl: MFCD00473856
• 分子量: 236.224
• InChiKey: GHGSQHBSHYQLED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  65.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-5-((5-methylfuran-2-yl)methylene)-1,3-dioxane-4,6-dione 在 diazoisobutyronitrile N-溴代丁二酰亚胺(NBS) 、 乙酸酐 作用下， 以 四氯化碳 、 乙醇 为溶剂， 生成 N-[5-[5-[(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl]furan-2-yl]-4-methyl-1,3-thiazol-2-yl]acetamide
  参考文献：
  名称：

  通过2-（5-R-糠基）硫脲鎓盐与乙酸酐的反应合成5-（5-R-2-糠基）噻唑衍生物

  摘要：

  DOI：

  10.1007/bf00497226
• 作为产物：
  描述：

  5-甲基呋喃醛 、 丙二酸环(亚)异丙酯 以 水 为溶剂， 反应 2.0h， 以83%的产率得到2,2-dimethyl-5-((5-methylfuran-2-yl)methylene)-1,3-dioxane-4,6-dione
  参考文献：
  名称：

  合成（E）-α，β-不饱和酸的实用便捷方案†

  摘要：

  α，β-不饱和酸是有机合成中非常有用且用途广泛的试剂。描述了一种新颖，实用且方便的催化方案，该方案包括在CH 3 NO 2中包含FeCl 3 ·6H 2 O（0.5 mol％）和H 2 O（1当量）的方法，用于快速合成具有高E的α，β-不饱和酸在具有高TON和TOF值的微波和常规加热条件下均具有-立体选择性。这种强大的方法有效地证明了生物质衍生醛在构建用作燃料添加剂的化学试剂方面的实用性。该方法被证明可扩展至克级合成。

  DOI：

  10.1021/ol402130t

文献信息

• An expedient stereoselective synthesis of ( E )- α,β -unsaturated esters and thioesters using FeCl 3 ·6H 2 O
  作者：Amar R. Mohite、Trimbak B. Mete、Ramakrishna G. Bhat

  DOI：10.1016/j.tetlet.2017.01.024

  日期：2017.2

  Facile and convenient synthesis of α,β-unsaturated esters and thioesters from alkylidene derivatives of Meldrum’s Acid is described. This method uses catalytic amount of FeCl3·6H2O (0.001–0.005 equiv) with alcohols/thiols (1 equiv) in dry CH3NO2 followed by catalytic amount of piperidine. A variety of α,β-unsaturated esters and thioesters have been synthesized with high E-stereoselectivity in good

  描述了从Meldrum's Acid的亚烷基衍生物容易且方便地合成α，β-不饱和酯和硫代酯。该方法在干燥的CH 3 NO 2中使用催化量的FeCl 3 ·6H 2 O（0.001-0.005当量）与醇/硫醇（1当量），然后催化量的哌啶。已经以高至优异的产率合成了具有高E-立体选择性的多种α，β-不饱和酯和硫代酯。该方法的应用通过辛辛酸，防晒剂和其他对甲氧基肉桂酸酯的克规模合成得到证明。
• 2,2-Dimethyl-5-(5-r-2-furfurylidene)-1,3-dioxan-4,6-diones. 1. Synthesis, properties, and structure
  作者：G. D. Krapivin、V. G. Kul'nevich、N. I. Val'ter

  DOI：10.1007/bf00473480

  日期：1986.10
• Regioselective synthesis and molecular modeling study of vasorelaxant active 7,9-dioxa-1,2-diaza-spiro[4.5]dec-2-ene-6,10-diones
  作者：Adel S. Girgis、Nasser S.M. Ismail、Hanaa Farag、Wafaa I. El-Eraky、Dalia O. Saleh、Srinivasa R. Tala、Alan R. Katritzky

  DOI：10.1016/j.ejmech.2010.06.018

  日期：2010.9

  Nitrilimines (PhC-:N+:NR') generated in situ from hydrazonoyl chlorides 2a,b reacted regioselectively with 5-arylidene-2,2-dimethyl[1,3]dioxane-4,6-diones 1a-f to afford 1.3,4-triaryl-8,8-dimethyl-7,9-dioxa-1,2-diaza-spiro[4.5]dec-2-ene-6,10-diones 3a-1. In vitro vasodilation activity screening of the synthesized compounds using isolated thoracic aortic rings of male Wister rats pre-contracted with norepinephrine hydrochloride revealed considerable vasodilation activity: compounds 3f and 3j had IC50 (concentration necessary for 50% reduction of maximal norepinephrine hydrochloride induced contracture) of 0.325, 0.321 mM, respectively. Molecular modeling, including fitting to a 3D-pharma-cophore model using Discovery studio 2.1 programs and their docking into optimized alpha(1)-AR homology models as alpha(1)-AR antagonist showed high-docking score and fit values. The experimental in vitro vasodilation activity of compounds 3a-1 was consistent with the molecular modeling. (C) 2010 Elsevier Masson SAS. All rights reserved.
• 2,2-Dimethyl-5-(5-R-furfurylidene)-1,3-dioxane-4,6-diones. 3. Selective hydrogenation of the exocyclic double bond and three-dimensional structures of the reaction products
  作者：G. D. Krapivin、V. E. Zavodnik、N. I. Val'ter、V. K. Bel'skii、V. G. Kul'nevich

  DOI：10.1007/bf00487297

  日期：1989.9
• 5-[5-R-furfurylidene]-2,2-dimethyl-1,3-dioxane-4,6-diones 6. Synthesis, structure, and properties of substituted furylimino- and furfurylidenephosphoranes. Molecular and crystal structure of N-[5-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl-2-furylimino(triphenyl)phosphorane
  作者：G. D. Krapivin、N. I. Val'ter、V. E. Zavodnik、T. Ya. Kaklyugina、V. G. Kul'nevich

  DOI：10.1007/bf01165694

  日期：1994.3