2-imino-3-(N-methyl)carbamoyl-4-methyl-5,5-pentamethylene-2,5-dihydrofuran | 1108179-89-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 2-imino-3-(N-methyl)carbamoyl-4-methyl-5,5-pentamethylene-2,5-dihydrofuran
• 英文别名: 2-imino-N,4-dimethyl-1-oxaspiro[4.5]dec-3-ene-3-carboxamide
• CAS: 1108179-89-0
• 化学式: C₁₂H₁₈N₂O₂
• 分子量: 222.287
• InChiKey: BQRVGOXJOUNRHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  62.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-imino-3-(N-methyl)carbamoyl-4-methyl-5,5-pentamethylene-2,5-dihydrofuran 在 盐酸 作用下， 以 苯 为溶剂， 以98%的产率得到2-imino-3-(N-methyl)carbamoyl-4-methyl-5,5-pentamethylene-2,5-dihydrofuran hydrochloride
  参考文献：
  名称：

  The Synthesis of New 2-Iminoderivatives of 2,5-Dihydrofurans and Their Chemical Transformations

  摘要：

  The new 2-iminoderivatives of 2,5-dihydrofurans, their salts, and some products of their transformations have been synthesized by the interaction of accessible tertiary alpha-ketols with amides of cyanoacetic acid. It was showed that the data and the supposed mechanism of the above-mentioned interaction described previously in literature are incorrect and do not correspond to the reality.

  DOI：

  10.1080/00397910701739022
• 作为产物：
  描述：

  1-乙酰基环己醇 、 2-氰基-N-甲基乙酰胺 在 sodium ethanolate 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 生成 2-imino-3-(N-methyl)carbamoyl-4-methyl-5,5-pentamethylene-2,5-dihydrofuran
  参考文献：
  名称：

  呋喃并[3,4- c ]吡啶-3-酮的新C 4和C 1衍生物及相关化合物：对组成型蛋白酶体及其免疫同工型进行位点特异性抑制的证据

  摘要：

  一组18个新的去甲-头孢菌素（1,1-二甲基呋喃[3,4- c ]吡啶-3-一）的C 4和C 1衍生物，6个模型化合物（γ-和δ-内酯）和20个呋喃设计或合成了噻吩并[2,3- d ]-嘧啶-4-one相关化合物。测定每种化合物对20S组成型蛋白酶体（c20S）的CT-L，TL和PA蛋白水解活性的抑制。还可以在20S免疫蛋白酶体（i20S）上分析大多数性能良好的化合物。在呋喃吡啶环的C 4处有苄氨基并在C 1处二甲基化的化合物10是c20S的最有效的PA位点特异性抑制剂（我知道了50每次转化费用600 nM）不会显着抑制i20S PA位点（iPA）。在iPA催化位点的计算机对接分析中，对10个化合物的分析表明，通常在该组成性PA位点（cPA）上没有观察到该化合物及相关位姿。Thieno [2,3- d ]嘧啶-4-酮40具有TL位​​点特异性，在体外对c20S和i20S均具有轻度抑制作用（我知道了50脂蛋白

  DOI：

  10.1016/j.bmcl.2014.01.072

文献信息

• Synthesis of new derivatives of 2-imino-2,5-dihydrofurans
  作者：Aida Avetisyan、Lusine Karapetyan

  DOI：10.1515/hc-2012-0113

  日期：2012.12.1

  New N-substituted 2-imino-2,5-dihydrofurans were synthesized by using several efficient approaches starting from readily available 2-imino-2,5-dihydrofurans. All new compounds were characterized by NMR and IR spectral data and elemental analysis.

  通过使用几种高效方法，从易得的2-亚亚胺-2,5-二氢呋喃合成了新的N-取代的2-亚亚胺-2,5-二氢呋喃。所有新化合物均通过核磁共振和红外光谱数据以及元素分析进行了表征。

• Synthesis of 2-imino-4-vinyl-2,5-dihydrofuran-3-carboxamides and some their chemical transformations
  作者：A. A. Avetisyan、L. V. Karapetyan、M. D. Tadevosyan

  DOI：10.1134/s1070428009070082

  日期：2009.7

  2-Imino-2,5-dihydrofuran-3-carboxamides containing 2-phenyl- and 2-furylvinyl substituents in position 4 of the furan ring were synthesized by condensation of 2-imino-4-methyl-2,5-dihydrofuran-3-carboxamides with the corresponding aldehydes. Acid hydrolysis of 4-(2-arylvinyl)-2-imino-2,5-dihydrofuran-3-carboxamides gave 4-(2-arylvinyl)-2-oxo-2,5-dihydrofuran-3-carboxamides, and their condensation with malononitrile resulted in the formation of 2-dicyanomethylidene derivatives.
• Synthesis and hydrolysis of bicyclic 2-imino-2,5-dihydrofurans fused to a pyridine ring
  作者：A. A. Avetisyan、L. V. Karapetyan、M. D. Tadevosyan

  DOI：10.1134/s1070428010080257

  日期：2010.8
• The Synthesis of New 2-Iminoderivatives of 2,5-Dihydrofurans and Their Chemical Transformations
  作者：Aida Avetissyan、Lousine Karapetyan

  DOI：10.1080/00397910701739022

  日期：2008.12.16

  The new 2-iminoderivatives of 2,5-dihydrofurans, their salts, and some products of their transformations have been synthesized by the interaction of accessible tertiary alpha-ketols with amides of cyanoacetic acid. It was showed that the data and the supposed mechanism of the above-mentioned interaction described previously in literature are incorrect and do not correspond to the reality.
• New C4- and C1-derivatives of furo[3,4-c]pyridine-3-ones and related compounds: Evidence for site-specific inhibition of the constitutive proteasome and its immunoisoform
  作者：Anna Hovhannisyan、The Hien Pham、Dominique Bouvier、Alexander Piroyan、Laure Dufau、Lixian Qin、Yan Cheng、Gagik Melikyan、Michèle Reboud-Ravaux、Michelle Bouvier-Durand

  DOI：10.1016/j.bmcl.2014.01.072

  日期：2014.3

  furo[3,4-c]pyridine-3-one), 6 model compounds (γ- and δ-lactones) and 20 furo- or thieno[2,3-d]-pyrimidine-4-one related compounds were designed and synthesized. Each compound was assayed for inhibition of CT-L, T-L and PA proteolytic activities of 20S constitutive proteasome (c20S). Most performant compounds were also assayed on 20S immunoproteasome (i20S). Compound 10 with a benzylamino group at C4

  一组18个新的去甲-头孢菌素（1,1-二甲基呋喃[3,4- c ]吡啶-3-一）的C 4和C 1衍生物，6个模型化合物（γ-和δ-内酯）和20个呋喃设计或合成了噻吩并[2,3- d ]-嘧啶-4-one相关化合物。测定每种化合物对20S组成型蛋白酶体（c20S）的CT-L，TL和PA蛋白水解活性的抑制。还可以在20S免疫蛋白酶体（i20S）上分析大多数性能良好的化合物。在呋喃吡啶环的C 4处有苄氨基并在C 1处二甲基化的化合物10是c20S的最有效的PA位点特异性抑制剂（我知道了50每次转化费用600 nM）不会显着抑制i20S PA位点（iPA）。在iPA催化位点的计算机对接分析中，对10个化合物的分析表明，通常在该组成性PA位点（cPA）上没有观察到该化合物及相关位姿。Thieno [2,3- d ]嘧啶-4-酮40具有TL位​​点特异性，在体外对c20S和i20S均具有轻度抑制作用（我知道了50脂蛋白