N-(furan-2-ylmethyl)-2-nitrobenzamide | 120275-54-9

• 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: N-(furan-2-ylmethyl)-2-nitrobenzamide
• CAS: 120275-54-9
• 化学式: C₁₂H₁₀N₂O₄
• mdl: MFCD00734539
• 分子量: 246.222
• InChiKey: UACAWKQFCADZEV-UHFFFAOYSA-N

物化性质

• 熔点：
  101-106 °C
• 沸点：
  453.5±35.0 °C(Predicted)
• 密度：
  1.330±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  88.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(furan-2-ylmethyl)-2-nitrobenzamide 在 sodium hydroxide 、 锌 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以48%的产率得到2-(furan-2-ylmethyl)-1,2-dihydro-3H-indazol-3-one
  参考文献：
  名称：

  Indazolinones, a new series of redox-active 5-lipoxygenase inhibitors with built-in selectivity and oral activity

  摘要：

  Since the hypothetical mechanisms of hydroperoxydation of arachidonic acid by, respectively, 5-lipoxygenase (5-LPO) and cyclooxygenase (CO) involve a redox cycle, a compound which reduces 5-LPO and CO to their inactive state would give a nonselective inhibitor of both enzymes. Structural modifications of such a compound could be expected to give improved potency and selectivity for 5-LPO and oral activity. Such an approach has led to the discovery of 1,2-dihydroindazol-3-ones which are potent 5-LPO inhibitors with various degrees of selectivity. Structure-activity relationship studies indicated that while N-1,N-2-unsubstituted and N-1-substituted derivatives are orally inactive, N-2-alkyl derivatives are orally active and inhibit both 5-LPO and CO. In contrast, N-2-benzyl derivatives are selective for 5-LPO but possess only weak oral activity. Further structural modifications have identified ICI 207968 [1,2-dihydro-2-(3-pyridylmethyl)-3H-indazol-3-one, 21a] which combines potent oral activity and high selectivity. Methemoglobin (MHb) induction by 21a in dog blood precluded its development for clinical use. Attempts at dissociating 5-LPO inhibitory properties and MHb formation showed that MHb formation in vitro seemed to be related to the redox potential of the compounds whereas 5-LPO inhibition was not. This study led to a series of 4-(N-n-pentylcarbamoyl)indazolinones which maintained in vitro 5-LPO potency but did not induce MHb.

  DOI：

  10.1021/jm00107a023
• 作为产物：
  描述：

  邻硝基苯甲酸 在 吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 N-(furan-2-ylmethyl)-2-nitrobenzamide
  参考文献：
  名称：

  铜催化重排级联烯丙基胺化二氮杂七元杂环衍生物的一锅法合成

  摘要：

  提出了一种在三苯基膦存在下，以乙酰丙酮钼和三氟甲磺酸铜 (II) 为催化剂，从邻硝基苯甲酸N-烯丙基酰胺合成 1,4-苯二氮卓-5-酮的新型有效方法。该合成过程包括氮烯形成、C-H 键插入、C=C 键重排以及通过铜和钼催化介导的 C-N 键形成级联反应。该方法具有广泛的底物范围和中高产率（高达 90%），具有实际应用的可能性。

  DOI：

  10.1021/acs.joc.9b02710

文献信息

• Furan ring opening–pyrrole ring closure: a new synthetic route to aryl(heteroaryl)-annulated pyrrolo[1,2-a][1,4]diazepines
  作者：Alexander V. Butin、Tatyana A. Nevolina、Vitaly A. Shcherbinin、Igor V. Trushkov、Dmitry A. Cheshkov、Gennady D. Krapivin

  DOI：10.1039/c002994g

  日期：——

  presence of alkyl or aryl groups on amide nitrogen due to competitive furfuryl cation elimination. But alkylation of pyrrolo[1,2-a][1,4]benzodiazepines yields efficiently the corresponding N-alkyl derivatives. Steric effects also prevent cyclization due to reversibility of diazepine ring formation under these reaction conditions. However, the corresponding pyrrolo[1,2-a][1,4]benzodiazepines can be obtained

  描述了吡咯并[1,2- a ] [1,4]苯并二氮杂s的合成方法。该方法是基于用Na 2 O 3处理的N-（糠基）蒽酰胺的再循环。盐酸/醋酸 系统，并允许两者同时形成 地西平和吡咯环一步就形成。反应通过 呋喃开环成二酮部分，随后NH 2-基团与两个羰基官能团连续相互作用。由于竞争性糠基阳离子消除，该方法在酰胺氮上存在烷基或芳基的情况下效率不高。但是吡咯并[1,2- a ] [1,4]苯并二氮杂卓的烷基化有效地产生了相应的N-烷基衍生物。在这些反应条件下，由于二氮杂ring环形成的可逆性，立体效应也阻止了环化作用。但是，相应的吡咯并[1,2- a ] [1,4]苯并二氮杂卓可通过逐步方法获得，即1）呋喃环开环为aq。盐酸/醋酸 和2）在冰河处理下，将分离的氨基二酮环化 醋酸。合成吡咯并[1,2- a ] [1,4]苯并二氮杂卓的另一种有效方法是酸催化N-（糠基）-2-硝基苯甲酰胺的呋喃环开环，然后处理所形成的吡咯并[1
• Synthesis of Isoindolo[2,1-<i>a</i>]quinazoline-5,11-dione Derivatives<i>via</i>the Reductive One-Pot Reaction of<i>N</i>-Substituted 2-Nitrobenzamides and 2-Formylbenzoic Acids
  作者：Mohammad Mahdavi、Ramin Najafi、Mina Saeedi、Eskandar Alipour、Abbas Shafiee、Alireza Foroumadi

  DOI：10.1002/hlca.201200199

  日期：2013.3

  Various isoindolo[2,1‐a]quinazoline‐5,11‐dione derivatives 3 were synthesized in good yields by means of the reductive reaction of N‐substituted 2‐nitrobenzamides 1 and 2‐formylbenzoic acids 2 in the presence of SnCl2⋅2 H2O under reflux in EtOH (Scheme, Table). The procedure needed two steps, the reduction of the nitro group of the 2‐nitrobenzamide and ring closure by nucleophilic addition of the NH2

  各种异吲哚基[2,1-一个]喹唑啉-5,11-二酮衍生物3进行以良好的收率由的还原反应的方法合成ñ -取代的2- nitrobenzamides 1和2甲酰基酸2中的SnCl存在2 ⋅在EtOH中回流下的2 H 2 O（方案，表）。该过程需要两个步骤，即2-硝基苯甲酰胺的硝基还原和通过在甲酰基和羧酸CO基团上亲核加成NH 2基来闭环。
• OCinneide, Proceedings of the Royal Irish Academy. Section B: Biological, geological, and chemical science, 1943, vol. 49 B, p. 143,150
  作者：OCinneide

  DOI：——

  日期：——
• BRUNEAU, P.;DELVARE, C.;EDWARDS, M. P.;MCMILLAN, R. M., J. MED. CHEM. , 34,(1991) N, C. 1028-1036
  作者：BRUNEAU, P.、DELVARE, C.、EDWARDS, M. P.、MCMILLAN, R. M.

  DOI：——

  日期：——
• One-Pot Synthesis of Seven-Membered Heterocyclic Derivatives of Diazepines Involving Copper-Catalyzed Rearrangement Cascade Allyl-Amination
  作者：Yuepeng Chen、Xinglei Liu、Wei Shi、Shilong Zheng、Guangdi Wang、Ling He

  DOI：10.1021/acs.joc.9b02710

  日期：2020.4.17

  trifluoromethanesulfonate as catalysts in the presence of triphenylphosphine. This synthesis process involves nitrene formation, C–H bond insertion, C═C bond rearrangement, and C–N bond formation cascade reactions via copper- and molybdenum-catalyzed mediation. The method features a wide substrate scope and a moderate to high yield (up to 90%), exhibiting the possibility for practical applications

  提出了一种在三苯基膦存在下，以乙酰丙酮钼和三氟甲磺酸铜 (II) 为催化剂，从邻硝基苯甲酸N-烯丙基酰胺合成 1,4-苯二氮卓-5-酮的新型有效方法。该合成过程包括氮烯形成、C-H 键插入、C=C 键重排以及通过铜和钼催化介导的 C-N 键形成级联反应。该方法具有广泛的底物范围和中高产率（高达 90%），具有实际应用的可能性。