phaitanthrin-B | 1033722-03-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: phaitanthrin-B
• 英文别名: methyl 2-(6-hydroxy-12-oxo-6,12-dihydroindolo[2,1-b]quinazolin-6-yl)acetate；Phaitanthrins B；methyl 2-(6-hydroxy-12-oxoindolo[2,1-b]quinazolin-6-yl)acetate
• CAS: 1033722-03-0
• 化学式: C₁₈H₁₄N₂O₄
• 分子量: 322.32
• InChiKey: CGMNLIDQBYRXFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  79.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  phaitanthrin-B 在 sodium tetrahydroborate 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 6.0h， 以82%的产率得到(-)-(R,R)-3-hydroxy-2H-pyrrolo[2,3-b]indolo[5,5a,6-b,a]quinazoline-9-(8H)-7'-dione
  参考文献：
  名称：

  Aryne Insertion Reactions Leading to Bioactive Fused Quinazolinones: Diastereoselective Total Synthesis of Cruciferane

  摘要：

  Insertion reactions of an in situ generated arynes to a variety of suitably substituted 1,3-quinazolin-4-ones have been demonstrated for a new efficient one-step approach to a diverse range of fused quinazolinone architectures. The present protocol has been effectively utilized to accomplish the concise total synthesis of recently isolated bioactive natural products tryptanthrin, phaitanthrins A-C, and cruciferane.

  DOI：

  10.1021/ol4018062
• 作为产物：
  描述：

  4-喹唑啉酮-2-甲酸乙酯 在 碳酸氢钠 、 cesium fluoride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 6.75h， 生成 phaitanthrin-B
  参考文献：
  名称：

  Aryne Insertion Reactions Leading to Bioactive Fused Quinazolinones: Diastereoselective Total Synthesis of Cruciferane

  摘要：

  Insertion reactions of an in situ generated arynes to a variety of suitably substituted 1,3-quinazolin-4-ones have been demonstrated for a new efficient one-step approach to a diverse range of fused quinazolinone architectures. The present protocol has been effectively utilized to accomplish the concise total synthesis of recently isolated bioactive natural products tryptanthrin, phaitanthrins A-C, and cruciferane.

  DOI：

  10.1021/ol4018062

文献信息

• Copper-Catalyzed One-Pot Synthesis of Quinazolinones from 2-Nitrobenzaldehydes with Aldehydes: Application toward the Synthesis of Natural Products
  作者：Subrata Sahoo、Shantanu Pal

  DOI：10.1021/acs.joc.1c02343

  日期：2021.12.17

  A novel, efficient, and atom-economical approach for the construction of quinazolinones from 2-nitrobenzaldehydes has been unveiled via copper-catalyzed nitrile formation, hydrolysis, and reduction in one pot for the first time. In this reaction, urea is used as a source of nitrogen for nitrile formation, hydrazine hydrate is used for both the reduction of the nitro group and the hydrolysis of nitrile

  首次通过铜催化的腈形成、水解和还原在一个锅中揭示了一种从 2-硝基苯甲醛构建喹唑啉酮的新型、高效和原子经济的方法。在该反应中，尿素用作生成腈的氮源，水合肼用于硝基的还原和腈的水解，大气中的氧气用作唯一的氧化剂。该方法描绘了具有良好官能团耐受性的宽底物范围。此外，该方法还用于合成裂殖菌素、色胺菊酯、phaitanthrin-A、phaitanthrin-B和8 H-喹唑啉[4,3 - b ]quinazolin-8-one。
• Direct Catalytic Asymmetric Synthesis of β-Hydroxy Acids from Malonic Acid
  作者：Hang Gao、Zhenli Luo、Pingjin Ge、Junqian He、Feng Zhou、Peipei Zheng、Jun Jiang

  DOI：10.1021/acs.orglett.5b02891

  日期：2015.12.18

  A nickel(II) catalyzed asymmetric synthesis of β-hydroxy acids from malonic acid and ketones was developed, revealing for the first time the synthetic utility of malonic acid in the construction of chiral carboxyl acids; importantly, the synthetic potential of this strategy was further demonstrated by the rapid construction of cephalanthrin A, phaitanthrin B, cruciferane, and rice metabolites.

  开发了镍（II）催化由丙二酸和酮不对称合成β-羟基酸的方法，这首次揭示了丙二酸在手性羧酸的合成中的合成作用。重要的是，该方法的合成潜力通过快速构建头孢菌素A，紫杉醇B，十字花青素和大米代谢产物得到了进一步证明。
• Efficient chiral ¹H NMR analysis of indoloquinazoline alkaloids phaitanthrin A, cephalanthrin-A and their analogues with a chiral phosphoric acid
  作者：Chong-Xing Liu、Longzhangdi Zheng、Linjing Zhu、Hong-Ping Xiao、Xinhua Li、Jun Jiang

  DOI：10.1039/c7ob00823f

  日期：——

  A chiral phosphoric acid promoted enantioselective NMR recognition and determination of indoloquinazoline alkaloids phaitanthrin A, cephalanthrin-A and their analogues was described, which conveniently reveals their optical purities with high accuracy. Besides, pyrazine type tertiary alcohols, cyclic amino alcohols and diamines can also be well resolved under optimal conditions. Importantly, this methodology

  描述了一种手性磷酸促进对映体选择性NMR的识别以及吲哚喹唑啉生物碱类紫杉醇A，头孢菌素A及其类似物的测定，可方便地揭示其光学纯度。此外，吡嗪类叔醇，环状氨基醇和二胺在最佳条件下也能很好地拆分。重要的是，该方法还用于直接分析氨基酸金属盐催化的紫丹菊酯A的不对称合成的反应混合物，从而提供了高效获得最佳反应条件的途径。
• An efficient Selectfluor-mediated condensation of indoles and anthranilates for the synthesis of indoloquinazolinones
  作者：Xinzhe Wang、Zhipeng Wu、Guogang Tu、Yuanyue Zhao、Xiaodong Xiong

  DOI：10.1039/d3cc02673f

  日期：——

  Intermolecular fluorocyclization of indoles with anthranilates, which proceeded smoothly to give diverse indoloquinazolinone architectures under mild reaction conditions, has been developed. A wide range of substrates were compatible with this cyclization system. The synthetic fluorinated compounds could be modified by their conversion to various substituted quinazolinones for drug discovery. In addition

  吲哚与邻氨基苯甲酸盐的分子间氟环化反应在温和的反应条件下顺利进行，得到多种吲哚并喹唑啉酮结构。多种底物与该环化系统兼容。合成的氟化化合物可以通过转化为各种取代的喹唑啉酮来进行修饰，用于药物发现。此外，该方案已应用于生物活性天然生物碱 phaitanthrins A–B、cephalanthrin A 和 cruciferane 的简明全合成。
• Electrochemical Oxidation of Indoles to Access Tryptanthrins at Room Temperature
  作者：Ziyi Guo、Yi Liu、Hang Li、Jiaping Wu、Meihua Xie、Jitan Zhang

  DOI：10.1002/adsc.202301027

  日期：2024.1.30

  An electrooxidative reconstruction of the indole core under ambient conditions is reported, resulting in the construction of tryptanthrins. This electrochemical strategy simplifies molecular skeleton-hopping by employing commercially available NH-indole feedstock as the starting materials. Furthermore, the synthetic value of this skeletal reconstruction was demonstrated by divergent further transformations

  据报道，在环境条件下吲哚核心的电氧化重建，导致色胺酮的构建。这种电化学策略通过使用市售的 NH-吲哚原料作为起始材料，简化了分子骨架跳跃。此外，这种骨骼重建的综合价值通过不同的进一步变换得到了证明。涉及控制实验和循环伏安研究的初步机理研究表明电的必要性以及氧气和 TEMPO 的重要性，从而揭示了可能的反应途径。