1-acetyl-N-(2-methoxyphenyl)cyclopropanecarboxamide | 937733-19-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-acetyl-N-(2-methoxyphenyl)cyclopropanecarboxamide
• 英文别名: 1-acetyl-N-(2-methoxyphenyl)cyclopropane-1-carboxamide
• CAS: 937733-19-2
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: XYLLNJPCNXHHCQ-UHFFFAOYSA-N

物化性质

• 熔点：
  79-80 °C
• 沸点：
  407.4±25.0 °C(Predicted)
• 密度：
  1.257±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-acetyl-N-(2-methoxyphenyl)cyclopropanecarboxamide 在 四氯化锡 作用下， 以 xylene 为溶剂， 反应 10.34h， 生成 8-methoxy-4-methyl-2,3,4,9-tetrahydro[2,3-b]quinolin-4-ol
  参考文献：
  名称：

  双活化环丙烷的多米诺开环/再循环反应是呋喃喹啉衍生物合成的一种策略。

  摘要：

  DOI：

  10.1002/anie.200604276
• 作为产物：
  描述：

  邻甲氧基苯胺 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 15.5h， 生成 1-acetyl-N-(2-methoxyphenyl)cyclopropanecarboxamide
  参考文献：
  名称：

  Facile synthesis of furoquinoline and effects on radical-induced oxidation of DNA

  摘要：

  The aim of this work was to clarify the influences of the position of hydroxyl group and furo[2,3-b] moiety on the antioxidant effectiveness of quinoline. Thus, 4-methyl-2,3-dihydrofuro[2,3-b]quinolin-6-ol (PFQ), 4-methyl-2,3-dihydrofuro[2,3-b]quinolin-8-ol (OFQ), and 4-methyl-2,3-dihydrofuro[2,3-b]quinolin-7-ol (MFQ) were synthesized by a recyclization reaction of 1-acetyl-N-phenylcyclopropanecarboxamide in the presence of SnCl4 as the catalyst. The antioxidant capacities of PFQ, OFQ, and MFQ were evaluated in the experimental system of the oxidation of DNA caused by Cu2+/glutathione (GSH), (OH)-O-aEuro cent, and 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH). OFQ and PFQ were able to protect DNA against Cu2+/GSH- and (OH)-O-aEuro cent-induced oxidation because the furo[2,3-b] moiety was beneficial for stabilizing the produced furoquinoline radical. Moreover, MFQ can decrease the oxidation rate of AAPH-induced oxidation of DNA, while PFQ and OFQ can inhibit AAPH-induced oxidation of DNA for a period. The data obtained from AAPH-induced oxidation of DNA were treated by chemical kinetic method; it was found that PFQ and OFQ can trap 1.3 and 1.5 radicals, respectively. Therefore, the hydroxyl group at different positions changed the mechanism of furoquinoline in protecting DNA against radical-induced oxidation.Effects on Cu2+/glutathione-, (OH)-O-aEuro cent-, and peroxyl radical-induced oxidation of DNA.

  DOI：

  10.1007/s00044-012-0157-0

文献信息

• Ring-Enlargement of Dimethylaminopropenoyl Cyclopropanes: An Efficient Route to Substituted 2,3-Dihydrofurans
  作者：Rui Zhang、Yongjiu Liang、Guangyuan Zhou、Kewei Wang、Dewen Dong

  DOI：10.1021/jo801289p

  日期：2008.10.17

  A convenient and efficient synthesis of substituted dihydrofurans is developed via ring-enlargement of 1-dimethylaminopropenoyl-1-carbamoyl/benzoyl cyclopropanes catalyzed by ammonium acetate in acetic acid with high regio- and stereoselectivity. Some of the newly synthesized substituted dihydrofurans are subjected to further synthetic transformation in the presence of NaOH (aq) in ethanol to afford

  通过乙酸铵在乙酸中催化的1-二甲基氨基丙烯酰基-1-氨基甲酰基/苯甲酰基环丙烷的环区域选择性高和立体选择性高的合成，开发了一种方便高效的取代二氢呋喃合成方法。一些新合成的取代二氢呋喃在乙醇中的NaOH（水溶液）存在下进行进一步的合成转化，得到相应的5-芳基-2,3-二氢呋喃[3,2-c]吡啶-4（5H）-高产的。
• Efficient and Divergent Synthesis of Functionalized Cyclopropanes via Iodoform Reaction
  作者：Ning Zhang、Dewen Dong、Dingyuan Zhang、Rui Zhang、Dexuan Xiang、Yongjiu Liang

  DOI：10.1055/s-0031-1289693

  日期：2012.3

  Efficient and divergent one-pot synthesis of cyclopropyl amides and esters from readily available 1-acetylcyclopropanes via iodoform reaction based on the selection of reaction conditions is reported. A series of substituted cyclopropyl amides were synthesized from 1-acetylcyclopropanes, iodine, and ammonia in water in the presence of K2CO3 in good yields, whereas substituted cyclopropyl esters were

  据报道，基于反应条件的选择，通过碘仿反应从易得的1-乙酰基环丙烷通过一锅法高效，多样地合成了环丙基酰胺和酯。在K 2 CO 3存在下，由1-乙酰基环丙烷，碘和氨在水中以高收率合成了一系列取代的环丙基酰胺，而由1-乙酰基环丙烷与碘和醇在乙醇中的反应制得了取代的环丙基酯。 DBU的存在。 环丙烷-碘仿反应-碘-酰胺-水
• Efficient One-Pot Synthesis of Highly Substituted Pyridin-2(1<i>H</i>)-ones via the Vilsmeier−Haack Reaction of 1-Acetyl,1-Carbamoyl Cyclopropanes
  作者：Wei Pan、Dewen Dong、Kewei Wang、Jie Zhang、Rigenhada Wu、Dexuan Xiang、Qun Liu

  DOI：10.1021/ol070905i

  日期：2007.6.1

  A facile and efficient one-pot synthesis of highly substituted pyridin-2(1H)-ones is developed via the Vilsmeier-Haack reaction of readily available 1-acetyl,1-carbamoyl cyclopropanes, and a mechanism involving sequential ring-opening, haloformylation, and intramolecular nucleophilic cyclization reactions is proposed.

  通过容易获得的1-乙酰基，1-氨基甲酰基环丙烷的Vilsmeier-Haack反应以及涉及顺序开环，卤代甲酰化，并提出了分子内亲核环化反应。
• Regiospecific β-lactam ring-opening/recyclization reactions of N-aryl-3-spirocyclic-β-lactams catalyzed by a Lewis–Brønsted acids combined superacid catalyst system: a new entry to 3-spirocyclicquinolin-4(1H)-ones
  作者：Yinqiao Hu、Xiaolan Fu、Badru-Deen Barry、Xihe Bi、Dewen Dong

  DOI：10.1039/c1cc15881c

  日期：——

  The regiospecific β-lactam ring-opening/recyclization reaction of N-aryl-3-spirocyclic-β-lactams, made by the one-pot cyclization reaction of acetoacetanilides, has been achieved for the first time using a Lewis–Brønsted acids combined superacid catalyst system, thus providing an efficient entry to 3-spirocyclicquinolin-4(1H)-ones. A mechanism involving superacid-catalysis was proposed.

  N-芳基-3-螺环-β-内酰胺的区域特异性β-内酰胺环开环/重环化反应通过一次性环化反应合成的乙酰乙酸苯胺首次实现，采用了路易斯-布朗斯特酸联合超酸催化剂系统，从而为3-螺环喹啉-4(1H)-酮提供了高效的合成途径。提出了一种涉及超酸催化的机制。
• Efficient and Divergent Synthesis of Fully Substituted 1<i>H</i>-Pyrazoles and Isoxazoles from Cyclopropyl Oximes
  作者：Kewei Wang、Dexuan Xiang、Jinying Liu、Wei Pan、Dewen Dong

  DOI：10.1021/ol800178x

  日期：2008.5.1

  Efficient and divergent one-pot synthesis of fully substituted 1H-pyrazoles and isoxazoles from cyclopropyl oximes based on reaction conditions selection is reported. Under Vilsmeier conditions (POCl3/DMF), substituted 1 H-pyrazoles were synthesized from 1-carbamoyl, 1-oximyl cyclopropanes via sequential ring-opening, chlorovinylation, and intramolecular aza-cyclization. In the presence of POCl3/CH2Cl2

  据报道，根据反应条件的选择，可以从环丙基肟中高效，多样地一锅合成全取代的1H-吡唑和异恶唑。在Vilsmeier条件（POCl3 / DMF）下，通过顺序开环，氯乙烯基化和分子内氮杂环化反应，由1-氨基甲酰基，1-肟基环丙烷合成取代的1 H-吡唑。在POCl3 / CH2Cl2存在下，通过开环和分子内亲核乙烯基取代（SNV）反应从环丙基肟中获得取代的异恶唑。