3-((3r,5r,7r)-adamantan-1-yl)-1-phenyl-1H-pyrazol-5(4H)-one | 112351-69-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 3-((3r,5r,7r)-adamantan-1-yl)-1-phenyl-1H-pyrazol-5(4H)-one
• 英文别名: 1-Phenyl-3-adamantyl-(1)-pyrazolon-(5)；3-(1-adamantyl)-1-phenyl-1H-pyrazol-5-one；3-(1-adamantyl)-1-phenyl-4,5-dihydro-1H-pyrazol-5-one；5-adamantan-1-yl-2-phenyl-1,2-dihydro-pyrazol-3-one；3-(1-adamantyl)-1-phenyl-4,5-dihydropyrazol-5-one；5-(1-adamantyl)-2-phenyl-4H-pyrazol-3-one
• CAS: 112351-69-6
• 化学式: C₁₉H₂₂N₂O
• 分子量: 294.396
• InChiKey: LEVBDJAAMGVVRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-((3r,5r,7r)-adamantan-1-yl)-1-phenyl-1H-pyrazol-5(4H)-one 在 溶剂黄146 、 sodium nitrite 作用下， 反应 3.0h， 以100%的产率得到3-(1-adamantyl)-4-hydroxyimino-1-phenyl-4,5-dihydro-1H-pyrazol-5-one
  参考文献：
  名称：

  Synthesis and Some Chemical Transformations of Adamantyl-Substituted Pyrazolones

  摘要：

  1-Substituted 3-(1-adamantyl)-4,5-dihydro-1H-pyrazol-5-ones and 3-(1-adamantyl)-4,5-dihydroiso-xazol-5-one were synthesized by reaction of ethyl 3-(1-adamantyl)-3-oxopropanoate with various hydrazine derivatives and hydroxylamine hydrochloride. Nitrosation of adamantyl-substituted pyrazolones with sodium nitrite in acetic acid gave the corresponding 4-hydroxyimino derivatives. Reactions of 3-(1-adamantyl)-4,5-di-hydro-1H-pyrazol-5-ones and 3-(1-adamantyl)-4,5-dihydroisoxazol-5-one with aromatic and heterocyclic aldehydes led to the formation of condensation products at position 4 of the heteroring.

  DOI：

  10.1134/s1070428010100209
• 作为产物：
  描述：

  3-(1-金刚烷)-3-氧代丙酸乙酯 、 苯肼 在 溶剂黄146 作用下， 以85%的产率得到3-((3r,5r,7r)-adamantan-1-yl)-1-phenyl-1H-pyrazol-5(4H)-one
  参考文献：
  名称：

  Pyrazolones as inhibitors of immune checkpoint blocking the PD-1/PD-L1 interaction

  摘要：

  DOI：

  10.1016/j.ejmech.2022.114343

文献信息

• Quinazolin-4-one derivatives
  申请人：Itai Akiko

  公开号：US20060229324A1

  公开（公告）日：2006-10-12

  A medicament having an inhibitory activity against hematopoietic prostaglandin D2 synthase, which comprises as an active ingredient a compound represented by the following general formula (I) or a salt thereof: wherein X represents a group represented by the formula —N═C(R 5 )— or the formula —NH—CH(R 5 )—, R 1 , R 2 , R 3 , and R 4 represent a hydrogen atom, a halogen atom, a C 1 to C 6 alkyl group, or a hydroxy group, R 5 represents a C 1 to C 6 alkyl group or a C 6 to C 10 aryl group, and R represents an amino group.

  一种具有对造血前列腺素D2合成酶抑制活性的药物，其包括以下一般式（I）所代表的化合物或其盐作为活性成分： 其中X代表由式—N═C(R5)—或式—NH—CH(R5)—所代表的基团，R1、R2、R3和R4代表氢原子、卤原子、C1到C6烷基或羟基，R5代表C1到C6烷基或C6到C10芳基，R代表氨基。
• Pyrazolones as inhibitors of immune checkpoint blocking the PD-1/PD-L1 interaction
  作者：Raphaël Le Biannic、Romain Magnez、Frédérique Klupsch、Natascha Leleu-Chavain、Bryan Thiroux、Morgane Tardy、Hassiba El Bouazzati、Xavier Dezitter、Nicolas Renault、Gérard Vergoten、Christian Bailly、Bruno Quesnel、Xavier Thuru、Régis Millet

  DOI：10.1016/j.ejmech.2022.114343

  日期：2022.6
• Synthesis and Some Chemical Transformations of Adamantyl-Substituted Pyrazolones
  作者：K. M. Bormasheva、S. A. Kon’kov、I. K. Moiseev

  DOI：10.1134/s1070428010100209

  日期：2010.10

  1-Substituted 3-(1-adamantyl)-4,5-dihydro-1H-pyrazol-5-ones and 3-(1-adamantyl)-4,5-dihydroiso-xazol-5-one were synthesized by reaction of ethyl 3-(1-adamantyl)-3-oxopropanoate with various hydrazine derivatives and hydroxylamine hydrochloride. Nitrosation of adamantyl-substituted pyrazolones with sodium nitrite in acetic acid gave the corresponding 4-hydroxyimino derivatives. Reactions of 3-(1-adamantyl)-4,5-di-hydro-1H-pyrazol-5-ones and 3-(1-adamantyl)-4,5-dihydroisoxazol-5-one with aromatic and heterocyclic aldehydes led to the formation of condensation products at position 4 of the heteroring.