1-Phenyl-3-methyl-4-p-methoxybenzyliden-5-pyrazolon | 39143-07-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-Phenyl-3-methyl-4-p-methoxybenzyliden-5-pyrazolon
• 英文别名: 4-(4-methoxy-benzylidene)-5-methyl-2-phenyl-2,4-dihydro-pyrazol-3-one；4-((Z)-4-methoxy-benzylidene)-5-methyl-2-phenyl-2,4-dihydro-pyrazol-3-one；4-((Z)-4-Methoxy-benzyliden)-5-methyl-2-phenyl-2,4-dihydro-pyrazol-3-on；(4Z)-4-(4-methoxybenzylidene)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one；(4Z)-4-[(4-methoxyphenyl)methylidene]-5-methyl-2-phenylpyrazol-3-one
• CAS: 39143-07-2
• 化学式: C₁₈H₁₆N₂O₂
• 分子量: 292.337
• InChiKey: WGISVRVYQCZWOR-ATVHPVEESA-N

物化性质

• 沸点：
  450.8±55.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-Phenyl-3-methyl-4-p-methoxybenzyliden-5-pyrazolon 生成 4-甲氧基苯甲醛
  参考文献：
  名称：

  FANGHAENEL, E.;AKHLAQ, M. S.;GROSSMANN, N., J. PRAKT. CHEM., 1985, 327, N 2, 209-219

  摘要：

  DOI：
• 作为产物：
  描述：

  苯肼 在 sodium acetate 、 溶剂黄146 作用下， 生成 1-Phenyl-3-methyl-4-p-methoxybenzyliden-5-pyrazolon
  参考文献：
  名称：

  有机磷烷催化的4-亚芳基吡唑啉酮和5-亚芳基噻唑酮的直接β-酰化与酰氯。

  摘要：

  报道了一种在有机膦催化的碱存在下用酰氯直接将亚芳基吡唑啉酮和噻唑酮进行β-酰化的有效方法。在无金属和温和条件下，通过串联磷-迈克尔加成/ O-酰化/分子内环化/重排序列制备了各种功能化的4-亚芳基吡唑啉酮和5-亚芳基噻唑酮衍生物。我们的机理研究表明，该反应具有很高的立体定向性，只能提供顺式异构体，并且该方法也可以按放大的比例放大，获得相似的功效。

  DOI：

  10.1021/acs.orglett.0c02408

文献信息

• H-Bond-Directing Organocatalyst for Enantioselective [4 + 2] Cycloadditions via Dienamine Catalysis
  作者：Shoulei Wang、Carles Rodriguez-Escrich、Miquel A. Pericàs

  DOI：10.1021/acs.orglett.5b03575

  日期：2016.2.5

  regio- and stereoselective [4 + 2] cycloaddition reaction to generate tetrahydropyranopyrazole frameworks has been developed. To this end, a dienamine-based catalytic strategy that relies on the H-bond-directing effect of the hydroxy group of a dinaphthylprolinol-type aminocatalyst has been used. This enables the synthesis of multifunctionalized heterocyclic derivatives with three contiguous stereocenters

  已经开发出有效的，高度区域选择性和立体选择性的[4 + 2]环加成反应以生成四氢吡喃并吡唑骨架。为此，已经使用了依赖于二萘基脯氨醇型氨基催化剂的羟基的H键导向作用的基于二烯胺的催化策略。这使得能够以良好的产率和优异的对映选择性合成具有三个连续的立体中心的多官能化杂环衍生物。
• Bis-pyrazolone for color photography
  申请人：EASTMAN KODAK CO

  公开号：US02706683A1

  公开（公告）日：1955-04-19

  a - 41 - 11 - (211 : 411 : 611 - Trichlorophenyl) - 31 - [3111 - (2111 : 4111 - di - tert. - amylphenoxyacetamido) - benzamido] - 51 - pyrazolonyl}} - 1 - phenyl - 3 - methyl - 4 - (p - methoxybenzyl) - 5 - pyrazolone is prepared by refluxing together 1-phenyl-3-methyl-4-(41-methoxybenzylidene) - 5 - pyrazolone and 1-(21 : 41 : 61 - trichlorophenyl) - 3 - [311\h - (2111 : 4111 - di - tert. - amylphenoxyacetamido) - benzamido] - 5 - pyrazolone in acetic acid containing sodium acetate. a -41 - (11 - Benzthiazolyl) - 31 - [(311 - tert. - amylphenoxy) - benzamido] - 51-pyrazolonyl}} - 1 - phenyl - 3 - amino - 4 - (p-methoxybenzyl) - 5 - pyrazolone, a - 41 - [11-phenyl - 31 - a - phenylbutyramido - 51 - pyrazolonyl]} - 1 - [411 - (4111 - tert. - butylphenoxy)-phenyl] - 3 - [41111 - (41111 - tert. - butylphenoxy)-phenyl] - carbamyl - 4 - (p - methoxybenzyl) - 5-pyrazolone, and a - 1 - (21 - benzthiazolyl) - 3-d - [41 - (311 - p - tert. - amylphenoxy) - benzamido phenyl] - valeramido - 5 - pyrazolonyl} - 1-phenyl - 3 - a - phenylbutyrylamino - 4 - p-methoxybenzyl - 5 - pyrazolone are similarly prepared. 1 - Phenyl - 3 - methyl - 4 - (41 - methoxybenzylidene) - 5 - pyrazolone is prepared by heating together 1 - phenyl - 3 - methyl - 5-pyrazolone and p-methoxybenzaldehyde in glacial acetic acid. 1-Benzthiazolyl-3-[31-(tert.-amylphenoxy) - benzamido] - 4 - p - methoxybenzylidene - 5 - pyrazolone and 1 - phenyl - 3-a - phenylbutyramido - 4 - anisal - 5 - pyrazolone are similarly prepared. 1 - [41 - [411 - Tert. - Butylphenoxy) - phenyl]-3 - [4111 - (41111 - tert. - butylphenoxy) - phenyl]-carbamyl - 5 - pyrazolone is prepared by acylating 4-tert.-butylphenoxyaniline with 1-(41 - tert. - butylphenoxy) - phenyl - 3 - carboxy-5-pyrazolone. 1 - (21 - Benzthiazolyl) - 3 - d - [41 - (311 - p-tert. - amylphenoxy) - benzamido] - phenylvaleramido) - 5 - pyrazolone is prepared by acylating 1 - (21 - benzthiazolyl) - 3 - (d - 41-aminophenylvaleramido) - 5 - pyrazolone with 4 - (31 - p - tert.-amylphenoxy) - benzoyl chloride. Specifications 524,154, 524,555, 541,589, [all in Group XX], 599,919 and 680,488 are referred to.

  将1-苯基-3-甲基-4-(对-甲氧基苄基)-5-吡唑酮与1-(2,4,6-三氯苯基)-3-[3-(2,4-二叔丁基苯氧基)苯基氨基]-5-吡唑酮在含有乙酸钠的冰醋酸中回流，制备出a-41-11-(苯并噻唑基)-31-[(3-叔丁基苯氧基)苯基氨基]-51-吡唑酮基}}-1-苯基-3-氨基-4-(对-甲氧基苄基)-5-吡唑酮，a-41-[11-苯基-31-a-苯基丁酰氨基-51-吡唑酮基]}-1-[4-(4-叔丁基苯氧基)苯基]-3-[4-(4-叔丁基苯氧基)苯基]羰基-4-(对-甲氧基苄基)-5-吡唑酮，以及a-1-(苯并噻唑基)-3-d-[41-(3-叔丁基苯氧基)苯基氨基苯基]戊酰氨基-5-吡唑酮}-1-苯基-3-a-苯基丁酰氨基-4-对-甲氧基苄基-5-吡唑酮同样制备。1-苯基-3-甲基-4-(对-甲氧基苄基)-5-吡唑酮通过在冰醋酸中加热1-苯基-3-甲基-5-吡唑酮和对-甲氧基苯甲醛制备。1-苯并噻唑基-3-[3-(叔丁基苯氧基)苯基氨基]-4-对-甲氧基苄基-5-吡唑酮和1-苯基-3-a-苯基丁酰氨基-4-苯甲醛-5-吡唑酮同样制备。1-[4-(叔丁基苯氧基)苯基]-3-[4-(4-叔丁基苯氧基)苯基]羰基-5-吡唑酮通过用1-(4-叔丁基苯氧基)苯基-3-羧基-5-吡唑酮酰化4-叔丁基苯氧基苯胺制备。1-(苯并噻唑基)-3-d-[4-(3-叔丁基苯氧基)苯基氨基]-苯基戊酰氨基-5-吡唑酮通过用1-(苯并噻唑基)-3-(d-4-氨基苯基戊酰氨基)-5-吡唑酮酰化4-(3-叔丁基苯氧基)苯甲酰氯制备。规格524,154, 524,555, 541,589，[均在XX组中]，599,919和680,488被引用。
• Highly stereoselective construction of spiro[cyclopropane-1,4′-pyrazolin-5′-one]with 4-arylidene-3-methyl-1-phenyl-pyrazolin-5-one and arsonium ylide
  作者：Zhongjiao Ren、Weiguo Cao、Jie Chen、Yali Chen、Hongmei Deng、Min Shao、Danyi Wu

  DOI：10.1016/j.tet.2008.03.049

  日期：2008.5

  A highly stereoselective synthesis of exo-spiro[cyclopropane-1,4′-pyrazolin-5′-one] from 4-arylidene-3-methyl-1-phenyl-pyrazolin-5-one and arsonium bromide in the presence of base has been achieved. The triphenylarsine-catalyzed cyclopropanation of 4-arylidene-3-methyl-1-phenyl-pyrazolin-5-one with bromide in the presence of NaHCO3 has also been studied. Both exo and endo isomers were formed in this

  在碱存在下，由4-亚芳基-3-甲基-1-苯基-吡唑啉-5-酮和溴化砷高度立体选择性地合成exo -spiro [cyclopropane-1,4'-pyrazolin-5'-one]实现了。在NaHCO 3存在下，还研究了三苯ar催化四溴化亚芳基-3-甲基-1-苯基-1-吡唑啉-5-酮的环丙烷化反应。两个外和内切形成在该反应中的异构体。产物的结构通过IR，MS，1 H NMR，元素分析和X射线衍射分析来表征。
• Synthesis of difluoromethylated spiropyrazolones <i>via</i> [3 + 2] cycloaddition of difluoroacetohydrazonoyl bromides with alkylidene pyrazolones
  作者：Yang Feng、Yuanyuan Ren、Duoduo Tang、Ke-Hu Wang、Junjiao Wang、Danfeng Huang、Xiaobo Lv、Yulai Hu

  DOI：10.1039/d4ob00044g

  日期：2024.4.3

  An effective [3 + 2] cycloaddition reaction of difluoromethyl or trifluoromethyl hydrazonoyl bromides with alkylidene pyrazolones was disclosed. This method provides an efficient approach for accessing a variety of highly functionalized fluoroalkyl spiropyrazolones in good yields. This protocol also features some advantages such as easily available and stable substrates, simple operation procedures

  公开了二氟甲基或三氟甲基亚肼酰溴与亚烷基吡唑啉酮的有效[3+2]环加成反应。该方法提供了一种以良好收率获得各种高度官能化的氟代烷基螺吡唑啉酮的有效方法。该方案还具有底物容易获得且稳定、操作程序简单、原子和步骤经济等优点。讨论了（顺式）-和（反式）-产物的形成。
• Ionescu; Popescu, Bulletin de la Societe Chimique de France, 1932, vol. <4>, p. 1215,1223
  作者：Ionescu、Popescu

  DOI：——

  日期：——