3-methyl-1-phenyl-1,4,5,6-tetrahydrocyclopenta[c]pyrazole | 108898-63-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-methyl-1-phenyl-1,4,5,6-tetrahydrocyclopenta[c]pyrazole
• 英文别名: 1-Phenyl-3-methyl-4,5-trimethylenepyrazole；3-methyl-1-phenyl-5,6-dihydro-4H-cyclopenta[c]pyrazole
• CAS: 108898-63-1
• 化学式: C₁₃H₁₄N₂
• 分子量: 198.268
• InChiKey: JNLKHVLZSRKGFM-UHFFFAOYSA-N

物化性质

• 沸点：
  325.9±11.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-乙酰基环戊酮 、 苯肼 在 tungstate sulfuric acid 作用下， 反应 0.5h， 以82%的产率得到3-methyl-1-phenyl-1,4,5,6-tetrahydrocyclopenta[c]pyrazole
  参考文献：
  名称：

  钨酸硫酸的吲哚和吡唑的合成方法

  摘要：

  钨酸盐硫酸催化的克诺尔反应是一种简单，快速，原子经济且绿色的方法，该方法以肼衍生物和ß-二羰基化合物在无溶剂条件下的缩合为基础，合成吲唑和吡唑衍生物。发现该催化剂可以回收和再利用而不会显着损失其活性。在干净的反应曲线，使用安全的催化剂和无溶剂的条件方面，该方法的使用为克诺尔合成提供了新颖且改进的修饰。

  DOI：

  10.1002/jccs.201400251

文献信息

• [EN] HETEROCYCLIC COMPOUNDS FOR THE TREATMENT OF STRESS-RELATED CONDITIONS<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES POUR LE TRAITEMENT D'ÉTATS LIÉS AU STRESS
  申请人：OTSUKA PHARMA CO LTD

  公开号：WO2010137738A1

  公开（公告）日：2010-12-02

  The present invention provides a novel heterocyclic compound. A heterocyclic compound represented by general formula (1) wherein, R1 and R2, each independently represent hydrogen; a phenyl lower alkyl group that may have a substituent(s) selected from the group consisting of a lower alkyl group and the like on a benzene ring and/or a lower alkyl group; or a cyclo C3-C8 alkyl lower alkyl group; or the like; R3 represents a lower alkynyl group or the like; R4 represents a phenyl group that may have a substituent(s) selected from the group consisting of a 1,3,4-oxadiazolyl group that may have e.g., halogen or a heterocyclic group selected from pyridyl group and the like; the heterocyclic group may have at least one substituent(s) selected from a lower alkoxy group and the like or a salt thereof.

  本发明提供了一种新颖的杂环化合物。一种由通式（1）表示的杂环化合物，其中，R1和R2分别独立表示氢；苯基较低烷基基团，可能在苯环和/或较低烷基基团上具有从较低烷基基团等组成的取代基；或环C3-C8烷基较低烷基基团；或类似物；R3表示较低炔基基团或类似物；R4表示可能具有从1,3,4-噁二唑基团（例如，卤素）或从吡啶基团等组成的取代基的苯基团；所述杂环基可能具有至少一个从较低烷氧基等选择的取代基或其盐。
• Small Molecule Library Synthesis Using Segmented Flow
  作者：Christina M. Thompson、Jennifer L. Poole、Jeffrey L. Cross、Irini Akritopoulou-Zanze、Stevan W. Djuric

  DOI：10.3390/molecules16119161

  日期：——

  Flow chemistry has gained considerable recognition as a simple, efficient, and safe technology for the synthesis of many types of organic and inorganic molecules ranging in scope from large complex natural products to silicon nanoparticles. In this paper we describe a method that adapts flow chemistry to the synthesis of libraries of compounds using a fluorous immiscible solvent as a spacer between reactions. The methodology was validated in the synthesis of two small heterocycle containing libraries. The reactions were performed on a 0.2 mmol scale, enabling tens of milligrams of material to be generated in a single 200 mL reaction plug. The methodology allowed library synthesis in half the time of conventional microwave synthesis while maintaining similar yields. The ability to perform multiple, potentially unrelated reactions in a single run is ideal for making small quantities of many different compounds quickly and efficiently.

  流动化学作为一种简便、高效且安全的合成技术，已获得广泛认可，适用于多种有机和无机分子的制备，其规模从复杂的大型天然产物到硅纳米颗粒不等。本文介绍了一种利用流动化学合成化合物库的方法，该方法采用氟烃不溶性溶剂作为反应间的间隔物。我们在合成两个含小杂环的化合物库中验证了该方法。反应规模为0.2毫摩尔，单次200毫升反应插件即可生成数十毫克的物质。与传统微波合成相比，该方法在保持相似产率的同时，将化合物库合成时间缩短了一半。能够在单次运行中进行多个潜在不相关的反应，这为快速高效地制备少量多种不同化合物提供了理想条件。
• A new and a convenient route to enaminones and pyrazoles
  作者：Bogdan Štefane、Slovenko Polanc

  DOI：10.1039/b108524g

  日期：2002.1.24

  A new method has been developed for the regioselective preparation of enaminones and pyrazoles from 1,3-diketonatoboron difluorides. The reactions proceed smoothly under mild reaction conditions, producing enaminones and pyrazoles in high yields.

  已经开发出一种新的方法用于区域选择性制备甲壳素。 烯胺 和 吡唑类由1，3-二酮基硼酸二氟化物制得。反应在温和的反应条件下平稳进行，产生烯胺 和 吡唑类 高产。
• HETEROCYCLIC COMPOUNDS FOR THE TREATMENT OF STRESS-RELATED CONDITIONS
  申请人：Takahashi Akira

  公开号：US20120065189A1

  公开（公告）日：2012-03-15

  The present invention provides a novel heterocyclic compound. A heterocyclic compound represented by general formula (1) wherein, R 1 and R 2 , each independently represent hydrogen; a phenyl lower alkyl group that may have a substituent(s) selected from the group consisting of a lower alkyl group and the like on a benzene ring and/or a lower alkyl group; or a cyclo C3-C8 alkyl lower alkyl group; or the like; R 3 represents a lower alkynyl group or the like; R 4 represents a phenyl group that may have a substituent(s) selected from the group consisting of a 1,3,4-oxadiazolyl group that may have e.g., halogen or a heterocyclic group selected from pyridyl group and the like; the heterocyclic group may have at least one substituent(s) selected from a lower alkoxy group and the like or a salt thereof.

  本发明提供了一种新型杂环化合物。所述杂环化合物的通式（1）表示，其中，R1和R2各自独立地表示氢；苯基低烷基，其可以在苯环上和/或低烷基上具有选自低烷基等的取代基；或环状C3-C8烷基低烷基；或类似物；R3表示低炔基或类似物；R4表示苯基，其可以具有选自1,3,4-噁二唑基（例如，卤素）或选自吡啶基等杂环基的取代基；所述杂环基可以具有至少一个选自低烷氧基等的取代基或其盐。
• Synthesis, <i>in silico</i> modelling, and <i>in vitro</i> biological evaluation of substituted pyrazole derivatives as potential anti-skin cancer, anti-tyrosinase, and antioxidant agents
  作者：Samuel T. Boateng、Tithi Roy、Kara Torrey、Uchechi Owunna、Sergette Banang-Mbeumi、David Basnet、Eleonora Niedda、Alexis D. Alexander、Denzel El Hage、Siriki Atchimnaidu、Bolni Marius Nagalo、Dinesh Aryal、Ann Findley、Navindra P. Seeram、Tatiana Efimova、Mario Sechi、Ronald A. Hill、Hang Ma、Jean Christopher Chamcheu、Siva Murru

  DOI：10.1080/14756366.2023.2205042

  日期：2023.12.31

  prominent-phenotypic actives to engage diverse cancer/hyperpigmentation-related targets with relatively high affinities. Altogether, promising early-stage hits were identified – some with multiple activities – warranting further hit-to-lead optimisation chemistry with further biological evaluations, towards identifying new skin-cancer and skin-pigmentation renormalising agents.

  抽象的 采用区域选择性贱金属催化和微波辅助方法合成了 25 种唑类化合物 ( P1 – P25 )，并通过高分辨率质谱 (HRMS)、核磁共振 (NMR) 和红外光谱 (IR) 分析进行了全面表征，并在计算机和体外评估了抗癌、抗酪氨酸酶和抗氧化活性。 P25对四种皮肤癌 (SC) 系的细胞表现出有效的抗癌活性，对黑色素瘤 (A375、SK-Mel-28) 或非黑色素瘤 (A431、SCC-12) SC 细胞的选择性高于非癌性 HaCaT 角质形成细胞。克隆形成、划伤和免疫印迹测定数据与抗增殖结果一致，其表达谱暗示内在和外在细胞凋亡激活。在蘑菇酪氨酸酶抑制测定中， P14是化合物中最有效的（50% 细胞死亡时的半最大抑制浓度，IC 50 15.9 μM），活性高于熊果苷和曲酸。此外， P6还表现出值得注意的自由基清除活性。此外，计算机对接和吸收、分布、代谢、排泄和毒性（ADMET）模拟预测