5-Methyl-1-(3-nitrophenyl)-2,8-dioxa-5-azonia-1-boranuidabicyclo[3.3.0]octane-3,7-dione | 1311484-45-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-Methyl-1-(3-nitrophenyl)-2,8-dioxa-5-azonia-1-boranuidabicyclo[3.3.0]octane-3,7-dione
• 英文别名: 5-methyl-1-(3-nitrophenyl)-2,8-dioxa-5-azonia-1-boranuidabicyclo[3.3.0]octane-3,7-dione
• CAS: 1311484-45-3
• 化学式: C₁₁H₁₁BN₂O₆
• 分子量: 278.029
• InChiKey: VGKKOQGJKGMZEY-UHFFFAOYSA-N

物化性质

• 熔点：
  211-215 °C

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-溴色烯-2-酮 、 5-Methyl-1-(3-nitrophenyl)-2,8-dioxa-5-azonia-1-boranuidabicyclo[3.3.0]octane-3,7-dione 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 水 、 甲苯 为溶剂， 以61%的产率得到6-(3-nitrophenyl)-2H-chromen-2-one
  参考文献：
  名称：

  Structure–Activity Relationship (SAR) Study of Ethyl 2-Amino-6-(3,5-dimethoxyphenyl)-4-(2-ethoxy-2-oxoethyl)-4H-chromene-3-carboxylate (CXL017) and the Potential of the Lead against Multidrug Resistance in Cancer Treatment

  摘要：

  Multidrug resistance (MDR) against standard therapies poses a serious challenge in cancer treatment, and there is a clinical need for new anticancer agents that would selectively target MDR malignancies. Our previous studies have identified a 4H-chromene system, CXL017 (4) as an example, that can preferentially kill MDR cancer cells. To further improve its potency, we have performed detailed structure-activity relationship (SAR) studies at the 3, 4, and 6 positions of the 4H-chromene system. The results reveal that the 3 and 4 positions prefer rigid and hydrophobic functional groups while the 6 position prefers a meta or para-substituted aryl functional group and the substituent should be small and hydrophilic. We have also identified and characterized nine MDR cancer cells that acquire MDR through different mechanisms and demonstrated the scope of our new lead, 9g, to selectively target different MDR cancers, which holds promise to help manage MDR in cancer treatment.

  DOI：

  10.1021/jm300515q

文献信息

• The Multiple Facets of Iodine(III) Compounds in an Unprecedented Catalytic Auto-amination for Chiral Amine Synthesis
  作者：Julien Buendia、Gwendal Grelier、Benjamin Darses、Amanda G. Jarvis、Frédéric Taran、Philippe Dauban

  DOI：10.1002/anie.201602022

  日期：2016.6.20

  Iodine(III) reagents are used in catalytic one‐pot reactions, first as both oxidants and substrates, then as cross‐coupling partners, to afford chiral polyfunctionalized amines. The strategy relies on an initial catalytic auto C(sp3)−H amination of the iodine(III) oxidant, which delivers an amine‐derived iodine(I) product that is subsequently used in palladium‐catalyzed cross‐couplings to afford a

  碘（III）试剂用于催化一锅法反应，首先用作氧化剂和底物，然后用作交叉偶联伙伴，以提供手性多官能胺。该策略依赖于碘（III）氧化剂的初始催化自动C（sp 3）-H胺化反应，该胺可提供胺衍生的碘（I）产品，该产品随后用于钯催化的交叉偶联中，从而提供多种具有高产量和出色的立体选择性的有用构建基块。这项研究证明了高价碘试剂的自我胺化的概念，这增加了芳基部分的价值。
• MIDA boronate allylation – synthesis of ibuprofen
  作者：David Phillips、Glen Brodie、Sarah Memarzadeh、Gi Lum Tang、David J. France

  DOI：10.1039/d0ra03338c

  日期：——

  MIDA boronates are among the most useful reagents for the Suzuki–Miyaura reaction. This chemistry typically generates new bonds between two aromatic rings, thereby restricting access to important areas of chemical space. Here we demonstrate the coupling of MIDA boronates to allylic electrophiles, including a new synthesis of the well-known COX inhibitor ibuprofen.

  MIDA 硼酸盐是铃木-宫浦反应最有用的试剂之一。这种化学通常会在两个芳环之间产生新的键，从而限制进入化学空间的重要区域。在这里，我们展示了 MIDA 硼酸盐与烯丙基亲电子试剂的偶联，包括众所周知的 COX 抑制剂布洛芬的新合成。
• Closed-loop optimization of general reaction conditions for heteroaryl Suzuki-Miyaura coupling
  作者：Nicholas H. Angello、Vandana Rathore、Wiktor Beker、Agnieszka Wołos、Edward R. Jira、Rafał Roszak、Tony C. Wu、Charles M. Schroeder、Alán Aspuru-Guzik、Bartosz A. Grzybowski、Martin D. Burke

  DOI：10.1126/science.adc8743

  日期：2022.10.28

  matrix down-selection, uncertainty-minimizing machine learning, and robotic experimentation to discover general reaction conditions. Application to the challenging and consequential problem of heteroaryl Suzuki-Miyaura cross-coupling identified conditions that double the average yield relative to a widely used benchmark that was previously developed using traditional approaches. This study provides a practical

  有机反应的一般条件很重要但很少见，识别它们的努力通常只考虑化学空间的狭窄区域。发现更一般的反应条件需要考虑从与反应条件的高维矩阵交叉的大基质基质衍生的广阔化学空间区域，使得详尽的实验不切实际。在这里，我们报告了一个简单的闭环工作流程，该工作流程利用数据引导矩阵向下选择、不确定性最小化机器学习和机器人实验来发现一般反应条件。应用于杂芳基 Suzuki-Miyaura 交叉偶联的具有挑战性和后果性的问题，确定了相对于先前使用传统方法开发的广泛使用的基准而言平均产量翻倍的条件。