6-bromo-3-nitro-2H-chromen-2-one | 88184-80-9

• 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-bromo-3-nitro-2H-chromen-2-one
• 英文别名: 2H-1-Benzopyran-2-one, 6-bromo-3-nitro-；6-bromo-3-nitrochromen-2-one
• CAS: 88184-80-9
• 化学式: C₉H₄BrNO₄
• 分子量: 270.039
• InChiKey: IJNZICFKDGQTCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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-bromo-3-nitro-2H-chromen-2-one 在 sodium tetrahydroborate 、 (S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(1-(dimethylamino)-3-(1H-indol-3-yl)propan-2-yl)thiourea 、 zinc 、 四丁基氟化铵 、 氯化铵 、 三氟乙酸 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 47.34h， 生成 (1'R,4S,9'R)-4'-bromospiro[1,3-oxazolidine-4,13'-8-oxatricyclo[7.3.1.02,7]trideca-2(7),3,5-triene]-2,11'-dione
  参考文献：
  名称：

  手性有机铵盐催化剂促进3-硝基香豆素的对映选择性Diels-Alder反应

  摘要：

  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。

  DOI：

  10.1055/s-0040-1707302
• 作为产物：
  描述：

  硝基乙酸甲酯 、 5-溴水杨醛 在 二乙胺盐酸盐 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以72%的产率得到6-bromo-3-nitro-2H-chromen-2-one
  参考文献：
  名称：

  A Convenient One-Flask Synthesis of 3-Nitrocoumarins

  摘要：

  DOI：

  10.1055/s-1983-30534

文献信息

• Efficient method for the synthesis of functionalized pyrazoles by catalyst-free one-pot tandem reaction of nitroalkenes with ethyl diazoacetate
  作者：Jian-Wu Xie、Zheng Wang、Wei-Jun Yang、Li-Chun Kong、Dong-Cheng Xu

  DOI：10.1039/b915231h

  日期：——

  The one-pot synthesis of multisubstituted pyrazole derivatives was achieved viacatalyst-free 1,3-dipolar cycloaddition of ethyl diazoacetate and nitroalkenes as the key step and elimination of the leaving group (NO2 or Br) followed by intramolecular proton transfer with satisfactory yields.

  一锅合成多取代的吡唑衍生物是通过无催化剂的1,3-偶极环加成反应实现的重氮乙酸乙酯和硝基烯烃作为关键步骤，消除离去基团（NO 2或Br），然后以令人满意的产率进行分子内质子转移。
• Efficient synthesis of functionalized 1,2,3-triazoles by catalyst-free 1,3-dipolar cycloaddition of nitroalkenes with sodium azide
  作者：Ting Wang、Xiao-Chun Hu、Xu-Jiao Huang、Xin-Sheng Li、Jian-Wu Xie

  DOI：10.1590/s0103-50532012000600017

  日期：——

  A simple and efficient protocol has been developed for the synthesis of 1,2,3-triazole derivatives by catalyst-free 1,3-dipolar cycloaddition of nitroalkenes with sodium azide under mild conditions.

  已经开发了一种简单有效的方案，用于在温和条件下通过无催化剂的硝基烯烃与叠氮化钠的1,3-偶极环加成反应来合成1,2,3-三唑衍生物。
• Copper(I) phosphoramidite catalyzed asymmetric conjugate addition of dialkylzinc reagents of α,β-unsaturated nitroacetates; an enantioselective route to β-aryl-nitroalkanes
  作者：Jos P.G. Versleijen、Albert M. van Leusen、Ben L. Feringa

  DOI：10.1016/s0040-4039(99)01118-1

  日期：1999.7

  The asymmetric copper(I) phosphoramidite catalyzed conjugate addition of dialkylzinc reagents to E,Z-mixtures of α,β-unsaturated nitroacetates provided the 1,4-adducts in excellent yields but with low e.e.'s. High enantioselectivities (e.e.'s up to 92%) were obtained with structurally rigid 3-nitrocoumarins, leading to a new route to optically active β-aryl-nitroalkanes.

  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。
• l-Proline catalyzed condensation of salicylaldehydes with ethyl nitroacetate: an efficient access to 3-nitrocoumarins
  作者：Rajesh Kumar Sharma、Priyanka、Diksha Katiyar

  DOI：10.1007/s00706-016-1736-4

  日期：2016.12

  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

  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
• 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。