6-methyl-3-nitro-2H-chromen-2-one | 244029-31-0

• 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: 6-methyl-3-nitro-2H-chromen-2-one
• 英文别名: 6-methyl-3-nitrocoumarin；6-Methyl-3-nitrocoumarin；6-methyl-3-nitrochromen-2-one
• CAS: 244029-31-0
• 化学式: C₁₀H₇NO₄
• 分子量: 205.17
• InChiKey: MRRKEUKDMYOJQN-UHFFFAOYSA-N

物化性质

• 沸点：
  366.5±31.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-methyl-3-nitro-2H-chromen-2-one 在 sodium hydroxide 、 phosphoramidite 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 16.0h， 生成 4-methyl-2-(1-nitropropan-2-yl)phenol
  参考文献：
  名称：

  亚磷酰胺铜（I）催化α，β-不饱和硝基乙酸二烷基锌试剂的不对称共轭加成；β-芳基-硝基烷烃的对映选择性路线

  摘要：

  不对称铜（I）亚磷酰胺催化将二烷基锌试剂共轭加成到α，β-不饱和硝基乙酸酯的E，Z混合物中，从而以优异的收率提供1,4加合物，但ee较低。使用结构刚性的3-硝基香豆素可实现高对映选择性（ee高达92％），从而开辟了一种新的制备旋光性β-芳基-硝基烷烃的途径。

  DOI：

  10.1016/s0040-4039(99)01118-1
• 作为产物：
  描述：

  硝基乙酸乙酯 、 5-甲基水杨醛 在 L-脯氨酸 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以82%的产率得到6-methyl-3-nitro-2H-chromen-2-one
  参考文献：
  名称：

  l -Proline catalyzed condensation of salicylaldehydes with ethyl nitroacetate: an efficient access to 3-nitrocoumarins

  摘要：

  Abstractl-Proline catalyzed condensation of salicylaldehydes and ethyl nitroacetate afforded 3-nitrocoumarins in good to high yields under mild conditions. This organocatalyzed process offers a much improved yield of 3-nitrocoumarins and well tolerates both electron-donating and electron-withdrawing substituents on the phenyl ring. Graphical abstract

  DOI：

  10.1007/s00706-016-1736-4

文献信息

• Enantioselective Diels–Alder Reaction of 3-Nitrocoumarins Promoted by Chiral Organoammonium Salt Catalysts
  作者：Akira Sakakura、Yudai Fujii、Ryota Nakao、Saki Sugihara、Keita Fujita、Yuya Araki、Takayuki Kudoh、Ichiro Hayakawa、Haruki Mizoguchi

  DOI：10.1055/s-0040-1707302

  日期：2020.12

  An enantioselective Diels–Alder reaction of 3-nitrocoumarins has been developed. A tryptophan-derived C 1-symmetric organoammonium thiourea catalyst promoted the reaction of 3-nitrocoumarins with Danishefsky’s diene to give the corresponding adducts with good enantioselectivity (up to 94% ee). One of the resulting adducts was converted into a chiral carbocyclic quaternary β-amino alcohol.

  已经开发了 3-硝基香豆素的对映选择性 Diels-Alder 反应。色氨酸衍生的 C 1-对称有机铵硫脲催化剂促进了 3-硝基香豆素与丹麦谢夫斯基二烯的反应，得到具有良好对映选择性（高达 94% ee）的相应加合物。所得加合物之一被转化为手性碳环季 β-氨基醇。
• Diastereoselective Tandem Michael Additions of Indoles to 3-Nitrocoumarin Derivatives and Methyl Vinyl Ketone
  作者：Yong Tang、Meng-Chun Ye、Yao-Yu Yang、Xiu-Li Sun、Zhi Ma、Wei-Min Qin

  DOI：10.1055/s-2006-932472

  日期：——

  Tandem Michael additions of indole derivatives to 3-nitrocoumarins 2, followed by MVK, in one pot, has been developed for the synthesis of multi-functionalized 3,4-dihydrocoumarins bearing a quaternary stereocenter. The reaction proceeds with high diastereoselectivities in good to excellent yields.

  已开发出将吲哚衍生物串联迈克尔加成到 3-硝基香豆素 2，然后是 MVK，在一锅中，用于合成带有四元立体中心的多功能化 3,4-二氢香豆素。该反应以高非对映选择性进行，产率良好至极好。
• Intensified synthesis of [3,4-d]triazole-fused chromenes, coumarins, and quinolones
  作者：Georg Schwendt、Toma Glasnov

  DOI：10.1007/s00706-016-1885-5

  日期：2017.1

  AbstractEfficient and metal-free synthesis of [3,4-d]triazole-fused chromenes, coumarins, and quinolones has been achieved in an intensified regime using microwave heating. The smooth 1,3-dipolar cycloaddition reaction of heterocyclic nitroalkenes with sodium azide provides a rapid entry into valuable heterocyclic scaffolds with potential biological properties. Graphical abstract

  摘要使用微波加热在强化过程中​​已经实现了[3,4- d ]三唑稠合的色烯，香豆素和喹诺酮的高效无金属合成。杂环硝基烯烃与叠氮化钠的平滑1,3-偶极环加成反应可快速进入有价值的具有潜在生物学特性的杂环支架。 图形概要
• Looking for New Targets: Simple Coumarins as Antibacterial Agents
  作者：Maria Joao Matos、Saleta Vazquez-Rodriguez、Lourdes Santana、Eugenio Uriarte、Cristina Fuentes-Edfuf、Ysabel Santos、Angeles Munoz-Crego

  DOI：10.2174/1573406411208061140

  日期：2012.9.1

  The dramatic worldwide increase of dangerous infections by resistant and multi-resistant microbes makes the search of new molecules and new chemical entities an important topic in Medicinal Chemistry. As the ideal drug candidate has not been attained, an intensive search for new and innovative antimicrobials is still needed. A small series of 3- amino/nitrocoumarins without substitutions or substituted by methyl or methoxy groups at different positions were synthesized and evaluated for their antibacterial and antifungal activities against clinical isolates of Staphylococcus aureus, Escherichia coli and Candida albicans strains. Some of these structurally simple molecules exhibited antibacterial activity. The preliminary SAR study showed that the antibacterial activity against E. coli and S. aureus was dependent on the kind and position of the substitution pattern at the coumarin moiety.

  全球范围内由耐药和多重耐药微生物引起的危险感染急剧增加，使得 寻找新分子和新化学实体是药物化学的重要课题。作为理想的候选药物 虽然尚未实现，但仍需要深入寻找新的创新抗菌药物。小编整理了3- 合成了未取代或在不同位置被甲基或甲氧基取代的氨基/硝基香豆素 并评估其对金黄色葡萄球菌临床分离株的抗菌和抗真菌活性， 大肠杆菌和白色念珠菌菌株。其中一些结构简单的分子表现出抗菌活性。 初步SAR研究表明，对大肠杆菌和金黄色葡萄球菌的抗菌活性取决于 香豆素部分的取代模式的种类和位置。
• Lewis acid-controlled divergent condensation of 1,1-bis(methylthio)-2‑nitroethylene and salicylaldehydes for the synthesis of 3-nitrocoumarins and 4H-chromenes
  作者：Li Han、Xiaocao Quan、Xusheng Shao、Xiaoyong Xu、Zhong Li

  DOI：10.1016/j.tetlet.2022.154080

  日期：2023.3

  An efficient Lewis acid-controlled divergent synthesis of 3-nitrocoumarins and 4H-chromenes under mild conditions has been developed. The corresponding 3-nitrocoumarin products were obtained in moderate to excellent yields through FeCl3-catalyzed annulation of 1,1-bis (methylthio)-2‑nitroethylene with various salicylaldehydes, while 4H-chromene products were afforded by using BF3·OEt2 as catalyst with

  已开发出一种在温和条件下有效的路易斯酸控制发散合成 3-硝基香豆素和 4 H-色烯的方法。FeCl 3催化1,1-双(甲硫基)-2-硝基乙烯与各种水杨醛环化得到相应的3-硝基香豆素产物，收率中等，而4 H-色烯产物通过BF 3 ·OEt得到2作为具有相同起始原料的催化剂。