2-([1,1′-biphenyl]-4-yl)-1-(1H-pyrazol-1-yl)ethanone | 1609077-09-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-([1,1′-biphenyl]-4-yl)-1-(1H-pyrazol-1-yl)ethanone
• 英文别名: 2-([1,1'-biphenyl]-4-yl)-1-(1H-pyrazol-1-yl)ethanone；2-(4-Phenylphenyl)-1-pyrazol-1-ylethanone；2-(4-phenylphenyl)-1-pyrazol-1-ylethanone
• CAS: 1609077-09-9
• 化学式: C₁₇H₁₄N₂O
• 分子量: 262.311
• InChiKey: PVGBBYRWPRAWAA-UHFFFAOYSA-N

物化性质

• 熔点：
  101.8-102 °C
• 沸点：
  459.7±48.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tert-butyl 1-methyl-2-oxoindolin-3-ylidenecarbamate 、 2-([1,1′-biphenyl]-4-yl)-1-(1H-pyrazol-1-yl)ethanone 在 C₄₁H₄₂N₆O₅S₂ 作用下， 以 乙腈 为溶剂， 反应 9.0h， 以96%的产率得到tert-butyl ((R)-3-((S)-1-([1,1′-biphenyl]-4-yl)-2-oxo-2-(1H-pyrazol-1-yl)ethyl)-1-methyl-2-oxoindolin-3-yl)carbamate
  参考文献：
  名称：

  吡唑酰胺与伊斯丁衍生的酮亚胺的有机催化对映选择性曼尼希反应

  摘要：

  已开发出吡唑酰胺与靛红衍生的N -Boc酮亚胺的第一个有机催化对映选择性曼尼希反应，能够以良好的非对映和对映选择性（高达99％）提供基于2-氧吲哚的手性β-氨基酰胺，产率高（84-97％）。 ：1 dr和> 99％ee）。

  DOI：

  10.1021/jo500145w
• 作为产物：
  描述：

  4-联苯乙酸 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 2-([1,1′-biphenyl]-4-yl)-1-(1H-pyrazol-1-yl)ethanone
  参考文献：
  名称：

  Discovery libraries targeting the major enzyme classes: The serine hydrolases

  摘要：

  Two libraries of modestly reactive ureas containing either electron-deficient acyl anilines or acyl pyrazoles were prepared and are reported as screening libraries for candidate serine hydrolase inhibitors. Within each library is a small but powerful subset of compounds that serve as a chemotype fragment screening library capable of subsequent structural diversification. Elaboration of the pyrazole-based ureas provided remarkably potent irreversible inhibitors of fatty acid amide hydrolase (FAAH, apparent Ki=100-200 pM) complementary to those previously disclosed enlisting electron-deficient aniline-based ureas.

  DOI：

  10.1016/j.bmcl.2014.06.063

文献信息

• N-Acyl pyrazoles: Effective and tunable inhibitors of serine hydrolases
  作者：Katerina Otrubova、Shreyosree Chatterjee、Srijana Ghimire、Benjamin F. Cravatt、Dale L. Boger

  DOI：10.1016/j.bmc.2019.03.020

  日期：2019.4

  (urea > carbamate > amide) and the pyrazole C4 substituent (CN > H > Me). It was further demonstrated that the acyl chain of the N-acyl pyrazole ureas can be used to tailor the potency and selectivity of the inhibitor class to a targeted serine hydrolase. Thus, elaboration of the acyl chain of pyrazole-based ureas provided remarkably potent, irreversible inhibitors of fatty acid amide hydrolase (FAAH

  研究了一系列N-酰基吡唑作为候选的丝氨酸水解酶抑制剂，其中不仅可以通过酰基的性质来调节活性位点的酰化反应性和吡唑的离去基能力（反应性：酰胺>氨基甲酸酯>尿素） ，也可以通过吡唑C4取代为吸电子或供电子的取代基。它们对酶抑制活性的影响显示出显着效果，并且随着显着改变反应的羰基（脲>氨基甲酸酯>酰胺）和吡唑C4取代基（CN> H> Me）的性质，其活性显着提高。进一步证明，N-酰基吡唑脲的酰基链可用于调节抑制剂类别对靶向的丝氨酸水解酶的效力和选择性。因此，
• Diastereo‐ and Enantioselective Mannich/Cyclization Cascade Reaction Access to Chiral Benzothiazolopyrimidine Derivatives
  作者：Yan Zhang、Jia‐Hui Yang、Ying‐Qi Xia、Lin Dong、Fen‐Er Chen

  DOI：10.1002/chem.202005509

  日期：2021.4.7

  An efficient asymmetric Mannich/cyclization cascade strategy was established from 2‐benzothiazolimines with N‐acylpyrazoles to provide optical active benzothiazolopyrimidine derivatives using a copper‐based complex. The mild cascade process constructed various structurally diverse products with broad scope of substrates together with excellent enantioselectivities (up to 99 % ee) and diastereoselectivities

  一种有效的不对称曼尼希/环化级联策略是从2-苯并噻唑啉与N-酰基吡唑建立的，以使用铜基络合物提供光学活性的苯并噻唑并嘧啶衍生物。温和的级联过程构建了各种结构多样的产品，具有广泛的底物范围，同时具有出色的对映选择性（高达99％ee）和非对映选择性（高达99：1 dr）。
• An organocatalytic asymmetric Mannich reaction of pyrazoleamides with cyclic trifluoromethyl ketimines: enantioselective access to dihydroquinazolinone skeletons
  作者：Yuan Luo、Ke-Xin Xie、Deng-Feng Yue、Xiao-Mei Zhang、Xiao-Ying Xu、Wei-Cheng Yuan

  DOI：10.1039/c8ob00707a

  日期：——

  An organocatalyzed asymmetric Mannich reaction of pyrazoleamides and cyclic trifluoromethyl ketimines with a chiral bifunctional amine-squaramide as the catalyst was developed. A wide range of trifluoromethyl dihydroquinazolinone derivatives bearing adjacent quaternary and tertiary stereogenic centers were readily obtained in good to excellent yields (up to 99%) with high diastereo- and enantioselectivities

  吡唑酰胺和环状三氟甲基酮亚胺的有机催化不对称曼尼希反应，以手性双官能胺-方酸酰胺为催化剂进行了研究。容易获得具有相邻的四级和三级立体异构中心的各种三氟甲基二氢喹唑啉酮衍生物，具有良好的至优异的产率（高达99％），具有高非对映异构和对映选择性（高达99％ee和> 20：1 dr）。还证明了该产品的大规模实验和转化。
• Organocatalytic asymmetric Michael addition of pyrazoleamides to β -phthalimidonitroethene
  作者：Yuan Luo、Ke-Xin Xie、Deng-Feng Yue、Xiao-Mei Zhang、Xiao-Ying Xu、Wei-Cheng Yuan

  DOI：10.1016/j.tet.2017.09.019

  日期：2017.10

  A highly organocatalyzed asymmetric Michael addition reaction of pyrazoleamides to β-phthalimidonitroethene has been developed with a chiral bifunctional thiourea-tertiary amine as the catalyst. A wide range of γ-nitro β-amino amides were readily obtained in good to excellent yields with high diastereo- and enantioselectivities (up to 99% yield, 99% ee and >20:1 dr). The large scale experiment and

  以手性双官能硫脲-叔胺为催化剂，开发了高度有机催化的吡唑酰胺与β-邻苯二甲酰亚胺基硝基乙烯的迈克尔不对称加成反应。容易获得具有高非对映和对映选择性（高至99％收率，99％ee和> 20：1 dr的高非对映选择性）的各种γ-硝基β-氨基酰胺，产率高至优。还证明了该产品的大规模实验和转化。
• Discovery libraries targeting the major enzyme classes: The serine hydrolases
  作者：Katerina Otrubova、Venkat Srinivasan、Dale L. Boger

  DOI：10.1016/j.bmcl.2014.06.063

  日期：2014.8

  Two libraries of modestly reactive ureas containing either electron-deficient acyl anilines or acyl pyrazoles were prepared and are reported as screening libraries for candidate serine hydrolase inhibitors. Within each library is a small but powerful subset of compounds that serve as a chemotype fragment screening library capable of subsequent structural diversification. Elaboration of the pyrazole-based ureas provided remarkably potent irreversible inhibitors of fatty acid amide hydrolase (FAAH, apparent Ki=100-200 pM) complementary to those previously disclosed enlisting electron-deficient aniline-based ureas.