3-hydroxy-1-methyl-4-phenylquinolin-2(1H)-one | 94298-57-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-hydroxy-1-methyl-4-phenylquinolin-2(1H)-one
• 英文别名: N-methyl-4-phenyl-3-hydroxy-2-quinolone；3-hydroxy-1-methyl-4-phenyl-1H-quinolin-2-one；3-Hydroxy-1-methyl-4-phenylcarbostyril；N-Methyl-viridicatin；N-Methylviridicatin；3-Hydroxy-1-methyl-4-phenylquinolin-2-one
• CAS: 94298-57-4
• 化学式: C₁₆H₁₃NO₂
• 分子量: 251.285
• InChiKey: XWPKGECSARICSE-UHFFFAOYSA-N

物化性质

• 熔点：
  207-208 °C(Solv: ethanol (64-17-5))
• 沸点：
  397.3±42.0 °C(Predicted)
• 密度：
  1.293±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-hydroxy-1-methyl-4-phenylquinolin-2(1H)-one 、 氯化钍 在 氨 作用下， 以 乙醇 、 水 为溶剂， 以84%的产率得到
  参考文献：
  名称：

  Soliman, Ezzat M.; EL-Roudi, Ahmed M.; Hassaan, Aly M. A., Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 1989, vol. 19, p. 957 - 968

  摘要：

  DOI：
• 作为产物：
  描述：

  N-methyl-3-oxo-N,3-diphenylpropanamide 在 硫酸 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 二氯甲烷 为溶剂， 反应 2.2h， 生成 3-hydroxy-1-methyl-4-phenylquinolin-2(1H)-one
  参考文献：
  名称：

  One-Pot Synthesis of 3-Hydroxyquinolin-2(1H)-ones from N-Phenylacetoacetamide via PhI(OCOCF₃)₂-Mediated α-Hydroxylation and H₂SO₄-Promoted Intramolecular Cyclization

  摘要：

  A clean, one-pot synthesis of the biologically important 3-hydroxyquinolin-2(1H)-one compounds has been realized from the readily available N-phenylacetoacetamide derivatives through a PhI(OCOCF3)(2)-mediated alpha-hydroxylation and a H2SO4-promoted intramolecular condensation. The hydroxyl group in the generated alpha-hydroxylated intermediate can be well tolerated in the second H2SO4-promoted cyclization step.

  DOI：

  10.1021/jo400541s

文献信息

• Regioselective Ring Expansion of Isatins with <i>In Situ</i> Generated α-Aryldiazomethanes: Direct Access to Viridicatin Alkaloids
  作者：Yellaiah Tangella、Kesari Lakshmi Manasa、Namballa Hari Krishna、B. Sridhar、Ahmed Kamal、Bathini Nagendra Babu

  DOI：10.1021/acs.orglett.8b01417

  日期：2018.6.15

  A novel efficient one-pot regioselective ring-expansion reaction of isatins with in situ generated α-aryl/heteroaryldiazomethanes for the construction of viridicatin alkaloids has been described under metal-free conditions. The utility of this protocol is further demonstrated in the synthesis of naturally occurring viridicatin, viridicatol, and substituted 3-O-methyl viridicatin and their scale up

  在无金属条件下，已经描述了一种新型的靛红与原位生成的α-芳基/杂芳基重氮甲烷的有效的一锅区域选择性环扩环反应，用于构建ridicatin的生物碱。该协议的效用在天然存在的viridicatin，viridicatol和取代的3- O-甲基viridicatin的合成及其规模放大中得到了进一步证明。
• Pinacol Rearrangement of 3,4-Dihydro-3,4-dihydroxyquinolin-2(1<i>H</i>)-ones: An Alternative Pathway to Viridicatin Alkaloids and Their Analogs
  作者：Ondřej Rudolf、Michal Rouchal、Antonín Lyčka、Antonín Klásek

  DOI：10.1002/hlca.201300074

  日期：2013.10

  3‐Alkyl/aryl‐3‐hydroxyquinoline‐2,4‐diones were reduced with NaBH4 to give cis‐3‐alkyl/aryl‐3,4‐dihydro‐3,4‐dihydroxyquinolin‐2(1H)‐ones. These compounds were subjected to pinacol rearrangement by treatment with concentrated H2SO4, resulting in 4‐alkyl/aryl‐3‐hydroxyquinolin‐2(1H)‐ones. When a benzyl (Bn) group was present in position 3 of the starting compound, its elimination occurred during the

  用NaBH 4还原3-烷基/芳基-3-羟基喹啉-2,4-二酮，得到顺-3-烷基/芳基-3,4-二氢-3,4-二羟基喹啉-2（1 H）-1 。这些化合物通过用浓H 2 SO 4处理进行频哪醇重排，生成4-烷基/芳基-3-羟基喹啉-2（1 H）-酮。当起始化合物第3位存在苄基（Bn）时，在重排过程中会发生消除，并形成了相应的3-羟基喹啉-2（1 H）-1 。讨论了所有转化的反应机理。所有化合物的特征在于IR，1 H‐和13C-NMR光谱以及质谱。
• A Concise and Versatile Synthesis of Viridicatin Alkaloids from Cyanoacetanilides
  作者：Yusuke Kobayashi、Takashi Harayama

  DOI：10.1021/ol900255g

  日期：2009.4.2

  The efficient synthesis of 3-hydroxy-4-arylquinolin-2(1H)-ones through one-pot Knoevenagel condensation/epoxidation of cyanoacetanilides followed by decyanative epoxide-arene cyclization is described. A convergent assembly with functionalized aldehydes allows for rapid synthesis with diverse substitution patterns. Isolation of 3-hydroxy-4-arylquinolin-2(1H)-ones is readily accomplished by precipitation and filtration.
• Synthesis of Bisquinolone-Based Mono- and Diphosphine Ligands of the Aza-BINAP Type
  作者：Nuzhat Arshad、Jamshed Hashim、C. Oliver Kappe

  DOI：10.1021/jo800665t

  日期：2008.6.1

  Mono- and bisphosphine ligands based on the 4,4'-bisquinolone structural framework (BIQUIP ligands) were generated by direct microwave-assisted palladium-catalyzed carbon-phosphorus cross-coupling reactions employing the corresponding heteroaryl bromides and diphenylphosphine as substrates.
• Masoud, Mamdouh S.; Taha, Fouad; Soliman, Ezzat M., Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 1987, vol. 17, p. 881 - 900
  作者：Masoud, Mamdouh S.、Taha, Fouad、Soliman, Ezzat M.、Mohammed, Youssef S.

  DOI：——

  日期：——