N-cyclohexyl-2-oxo-2H-chromene-3-carboxamide | 4021-23-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: N-cyclohexyl-2-oxo-2H-chromene-3-carboxamide
• 英文别名: N-cyclohexyl-2-oxochromene-3-carboxamide
• CAS: 4021-23-2
• 化学式: C₁₆H₁₇NO₃
• mdl: MFCD00249896
• 分子量: 271.316
• InChiKey: KUWSPPXPGQEHSQ-UHFFFAOYSA-N

物化性质

• 熔点：
  152-254 °C(Solv: ethanol (64-17-5))
• 沸点：
  530.8±50.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• 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

安全信息

• 海关编码：
  2932209090

反应信息

• 作为反应物：
  描述：

  N-cyclohexyl-2-oxo-2H-chromene-3-carboxamide 、 1-溴环丁烷羧酸甲酯 在 六甲基磷酰三胺 、 mercury dichloride 、 锌 作用下， 以 苯 为溶剂， 反应 4.0h， 以47%的产率得到3-cyclohexylspiro[chromeno[3,4-c]pyridine-1,1'-cyclobutane]-2,4,5(3H,4aH,10bH)-trione
  参考文献：
  名称：

  Reaction of methyl 1-bromocycloalkanecarboxylates with zinc and N-cyclohexyl-2-oxo- and 6-bromo-N-cyclohexyl-2-oxochromene-3-carboxamides

  摘要：

  Methyl 1-bromocycloalkanecarboxylates reacted with zinc and N-cyclohexyl-2-oxo- or 6-bromo-N-cyclohexyl-2-oxochromene-3-carboxamides to give methyl 1-[3-(cyclohexylcarbamoyl)-2-oxochroman-4-yl]- or methyl 1-[6-bromo-3-(cyclohexylcarbamoyl)-2-oxochroman-4-yl]cycloalkanecarboxylates and 3-cyclohexyl- or 9-bromo-3-cyclohexylspiro[chromeno[3,4-c]pyridine-1,1'-cycloalkane]-2,4,5(3H,4aH,10bH)-triones.

  DOI：

  10.1134/s1070428015040090
• 作为产物：
  描述：

  水杨醛 在 N,N'-二环己基碳二亚胺 、 L-脯氨酸 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 N-cyclohexyl-2-oxo-2H-chromene-3-carboxamide
  参考文献：
  名称：

  3-amidocoumarins的合成，抗菌和几丁质酶抑制活性。

  摘要：

  已经合成了一系列3-amidocoumarins，并在体外测试了它们的抗微生物和几丁质酶抑制活性。其中，化合物5k，5l，8b-8d，8f和8g对某些测试菌株表现出良好的抗菌活性，MIC值在6.25-25 µg / mL范围内，而化合物5l，8b，8c和8f显示出良好的活性对抗至少一种或两种真菌菌株。某些被测化合物5d，5k，5l，8b和8c显示出显着的几丁质酶抑制活性，IC50值在3.74-5.6 µM范围内。其中5l被证明是有效的几丁质酶抑制剂，IC50值为3.74 µM。为了更好地理解酶-抑制剂的相互作用，所有合成化合物的分子对接研究均在烟曲霉几丁质酶1W9U上进行。化合物5l显示出与受体的高结合亲和力，结合能值为-8.44 Kcal / mol。该研究还提供了合成化合物的结构活性关系（SAR）。

  DOI：

  10.1016/j.bioorg.2020.103700

文献信息

• Design, synthesis and antifungal activity evaluation of coumarin-3-carboxamide derivatives
  作者：Xiang Yu、Peng Teng、Ya-Ling Zhang、Zhao-Jun Xu、Ming-Zhi Zhang、Wei-Hua Zhang

  DOI：10.1016/j.fitote.2018.03.013

  日期：2018.6

  A series of coumarin-3-carboxamides/hydrazides have been designed and synthesized, all the target compounds were evaluated in vitro for their antifungal activity against Botrytis cinerea, Alternaria solani, Gibberella zeae, Rhizoctorzia solani, Cucumber anthrax and Alternaria leaf spot, some of the designed compounds 4a-4g exhibited potential activity in the primary assays, this highlighted by the

  设计并合成了一系列香豆素-3-羧酰胺/酰肼，体外评估了所有目标化合物对灰霉病菌，链格孢菌，玉米赤霉菌，索氏根瘤菌，黄瓜炭疽和链霉菌叶斑的抗真菌活性。设计的化合物4a-4g在主要试验中表现出潜在的活性，这在化合物4a，4d，4e和4f中得到了突出显示，其对茄枯菌的EC50值低至1.80μg/ mL，2.50μg/ mL，2.25μg / mL和2.10μg/ mL分别显示出比Boscalid更有效的对照。此外，化合物4a和4e与Boscalid对灰葡萄孢的抗真菌活性相当。
• Cyclopropanation of N-Substituted 2-Oxochromene- and 6-Bromo-2-oxochromene-3-carboxamides with Zinc Enolates Derived from 1-Aryl-2,2-dibromoalkanones
  作者：V. V. Shchepin、P. S. Silaichev、R. V. Shchepin、M. A. Ezhikova、M. I. Kodess

  DOI：10.1007/s11178-005-0199-6

  日期：2005.4

  Zinc enolates derived from 1-aryl-2,2-dibromoalkanones react with N-cyclohexyl-2-oxochromene-3-carboxamides to give N-cyclohexyl-1-alkyl-1-aroyl-2-oxo-1a,7b-dihydrocyclopropa[c]chromene-1a-carboxamides mainly as cis isomers with respect to the substituents in positions 1 and 1a. Reactions of the same zinc enolates with N-benzyl-2-oxochromene-3-carboxamide and N-benzyl-6-bromo-2-oxochromene-3-carboxamide lead to formation of 1-aryl-2-benzyl- and 1-aryl-2-benzyl-6-bromo-1-hydroxy-9c-alkyl-1,2,9b,9c-tetrahydro-5-oxa-2-azacyclopenta[2,3]cyclopropa[1,2-a]naphthalene-3,4-diones. The reaction of zinc enolates with N-aryl-2-oxochromene-3-carboxamides in a weakly polar solvent (diethyl ether or ethyl acetate) affords mixtures of cis-N-aryl-1-aroyl-1-alkyl-2-oxo-1a,7b-dihydrocyclopropa[c]chromene-1a-carboxamides and their cyclic isomers, 9c-alkyl-1,2-diaryl-1-hydroxy-1,2,9b,9c-tetrahydro-5-oxa-2-azacyclopenta[2,3]cyclopropa[1,2-a]naphthalene-3,4-diones, the latter prevailing. N-Substituted 1-alkyl-1-aroyl-2-oxo-1a,7b-dihydrocyclopropa[c]chromene-1a-carboxamides in which the aroyl group on C1 and the carboxamide group on C1a are arranged trans are formed by reactions of zinc enolates with the corresponding 2-oxochromene-3-carboxamides in the presence of hexamethylphosphoric triamide.

  源自1-芳基-2,2-二溴代烷基酮的锌烯醇盐与N-环己基-2-氧代色烯-3-羧酰胺反应，主要生成顺式异构体，相对于位置1和1a的取代基，形式为N-环己基-1-烷基-1-芳酰基-2-氧代-1a,7b-二氢环丙[c]色烯-1a-羧酰胺。同样的锌烯醇盐与N-苄基-2-氧代色烯-3-羧酰胺和N-苄基-6-溴-2-氧代色烯-3-羧酰胺反应，生成1-芳基-2-苄基和1-芳基-2-苄基-6-溴-1-羟基-9c-烷基-1,2,9b,9c-四氢-5-氧-2-氮杂环戊[2,3]环丙[1,2-a]萘-3,4-二酮。锌烯醇盐与N-芳基-2-氧代色烯-3-羧酰胺在弱极性溶剂（乙醚或乙酸乙酯）中反应，得到顺式N-芳基-1-芳酰基-1-烷基-2-氧代-1a,7b-二氢环丙[c]色烯-1a-羧酰胺及其环状异构体，即9c-烷基-1,2-二芳基-1-羟基-1,2,9b,9c-四氢-5-氧-2-氮杂环戊[2,3]环丙[1,2-a]萘-3,4-二酮，后者占优势。在六甲基磷酸三胺存在下，锌烯醇盐与相应的2-氧代色烯-3-羧酰胺反应，生成N-取代的1-烷基-1-芳酰基-2-氧代-1a,7b-二氢环丙[c]色烯-1a-羧酰胺，其中C1上的芳酰基和C1a上的羧酰胺基团以反式排列。
• One-Step Synthesis of Chromene-3-Carboxamide, Bischromene, Chromeno[3,4-<i>c</i>]Pyridine and Bischromeno[3,4-<i>c</i>]Pyridine Derivatives for Antimicrobial Evaluation
  作者：Mohamed H. Helal、Gameel A. M. El-Hag Ali、Ahmed A. Ali、Yousry A. Ammar

  DOI：10.3184/030823410x12812852410870

  日期：2010.8

  Cyanoacetamide derivatives were reacted with salicylaldehyde under different conditions afforded chromenes and coumarin derivatives respectively. A number of chromeno[3,4-c]pyridine derivatives were prepared from the reaction of N-cyclohexyl-2-imino-2H-chromene-3-carboxamide with malononitrile and/or cynaothiocatemaide. Bischromeno[3,4-c]pyridine derivatives were prepared from the reaction of N,N’-(ethane-1

  氰乙酰胺衍生物在不同条件下与水杨醛反应，分别得到色烯和香豆素衍生物。许多 chromeno[3,4-c] 吡啶衍生物由 N-cyclohexyl-2-imino-2H-chromene-3-carboxamide 与丙二腈和/或 cynaothiocatemaide 反应制备。双色烯[3,4-c]吡啶衍生物由N,N'-(乙烷-1,2-二基)双(2-亚氨基-2H-色烯-3-甲酰胺)与丙二腈和/或N的反应制备-烷基-2-氰基乙酰胺衍生物分别与2-亚氨基铬衍生物。筛选了其中一些化合物的抗微生物活性。
• KPF₆-Mediated Esterification and Amidation of Carboxylic Acids
  作者：Sonam、Vikki N. Shinde、Anil Kumar

  DOI：10.1021/acs.joc.1c02611

  日期：2022.3.4

  been developed for the synthesis of esters and amides. A wide range of carboxylic acids and alcohols or amines worked well under the developed reaction conditions, thus providing good to excellent (61–98%) yields of the corresponding esters and amides. The method worked well with bioactive substrates such as cholesterol, levulinic acid, and linoleic acid. Wide substrate scope, operational simplicity

  已经开发了一种新的 KPF 6促进的绿色方法来合成酯和酰胺。广泛的羧酸和醇或胺在开发的反应条件下工作良好，因此提供了良好至优异（61-98%）的相应酯和酰胺产率。该方法适用于胆固醇、乙酰丙酸和亚油酸等生物活性底物。广泛的底物范围、操作简单性、可扩展性和可持续性使该协议成为制备酯和酰胺的实用且经济上有吸引力的方法。
• An efficient three-component synthesis of coumarin-3-carbamides by use of Ni–NiO nanoparticles as magnetically separable catalyst
  作者：Nayim Sepay、Chayan Guha、Arpan Kool、Asok K. Mallik

  DOI：10.1039/c5ra13932e

  日期：——

  An efficient and ecofriendly synthesis of coumarin-3-carbamides has been developed by a three-component reaction of 2-hydroxybenzaldehydes, aliphatic amines (p-/s-) and diethyl malonate using Ni–NiO nanoparticles as catalyst.

  使用Ni-NiO纳米颗粒作为催化剂，通过2-羟基苯甲醛、脂肪胺（p-/s-）和二乙基丙二酸酯的三组分反应，开发了一种高效、环保的香豆素-3-氨基甲酰化合物的合成方法。