1-(4-(1H-pyrrol-1-yl)phenyl)propan-2-one | 1284216-68-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(4-(1H-pyrrol-1-yl)phenyl)propan-2-one
• 英文别名: 1-(4-pyrrol-1-yl-phenyl)propan-2-one；1-(4-Pyrrol-1-ylphenyl)propan-2-one
• CAS: 1284216-68-7
• 化学式: C₁₃H₁₃NO
• 分子量: 199.252
• InChiKey: JXRJXEQNBASNOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-(1H-pyrrol-1-yl)phenyl methanesulfonate 、 丙酮 在 potassium phosphate 、 bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)] 、 N-[2-二(1-金刚烷)磷苯基]吗啉 作用下， 以 1,4-二氧六环 、 叔丁醇 为溶剂， 以75%的产率得到1-(4-(1H-pyrrol-1-yl)phenyl)propan-2-one
  参考文献：
  名称：

  应对甲磺酸烷基酯的钯催化交叉偶联中的挑战：酮和伯烷基胺的单芳基化

  摘要：

  甲基（甲酸酯）的Mor（DalPhos）：描述了使用甲磺酸甲磺酸酯偶合伙伴进行酮单α-芳基化和脂肪族伯胺单芳基化的第一个实例。与二烷基酮，伯胺和仲胺以及否则具有挑战性的偶联伙伴丙酮和甲胺一起使用了一系列官能化的甲磺酸烷基酯。Ad =金刚烷基。

  DOI：

  10.1002/anie.201303305

文献信息

• Design of an Indolylphosphine Ligand for Reductive Elimination-Demanding Monoarylation of Acetone Using Aryl Chlorides
  作者：Wai Chung Fu、Chau Ming So、Wing Kin Chow、On Ying Yuen、Fuk Yee Kwong

  DOI：10.1021/acs.orglett.5b02344

  日期：2015.9.18

  elimination-demanding Pd-catalyzed mono-α-arylation of acetone is demonstrated and reported. The catalyst is tolerant of previously proven challenging electron-deficient aryl chlorides and provides excellent product yields with down to 0.1 mol % Pd. Preliminary investigations suggest that the rate-limiting step for the proposed system is the oxidative addition of aryl chlorides, in which it contradicts

  证明并报道了膦配体的合理设计，该膦配体用于还原性消除要求的Pd催化的丙酮单α-芳基化反应。该催化剂可耐受先前证明的具有挑战性的缺乏电子的芳基氯化物，并能以低至0.1 mol％的Pd提供出色的产品收率。初步研究表明，所提出系统的限速步骤是氧化加成芳基氯，在该反应中，它与先前有关丙酮与芳基卤化物的α-芳基化的发现相矛盾。
• Nickel‐Catalyzed Mono‐Selective α‐Arylation of Acetone with Aryl Chlorides and Phenol Derivatives
  作者：Sary Abou Derhamine、Tetiana Krachko、Nuno Monteiro、Guillaume Pilet、Johannes Schranck、Anis Tlili、Abderrahmane Amgoune

  DOI：10.1002/anie.202006826

  日期：2020.10.19

  The challenging nickel‐catalyzed mono‐α‐arylation of acetone with aryl chlorides, pivalates, and carbamates has been achieved for the first time. A nickel/Josiphos‐based catalytic system is shown to feature unique catalytic behavior, allowing the highly selective formation of the desired mono‐α‐arylated acetone. The developed methodology was applied to a variety of (hetero)aryl chlorides including

  丙酮与芳基氯化物，新戊酸酯和氨基甲酸酯的具有挑战性的镍催化的单α-芳基化反应已首次实现。镍/ Josiphos基催化体系显示出独特的催化行为，可以高度选择性地形成所需的单α-芳基化丙酮。所开发的方法适用于各种（杂）芳基氯化物，包括生物学相关的衍生物。该方法已扩展到丙酮与苯酚衍生物的空前偶联。机理研究允许分离和表征关键的Ni 0和Ni II催化中间体。已证明Josiphos配体在稳定Ni II中间体以产生Ni 0方面起关键作用/ Ni II催化途径。然后利用对空气稳定的Ni II预催化剂，利用机理上的理解来改进方案。
• Palladium-Catalyzed Mono-α-arylation of Acetone with Aryl Halides and Tosylates
  作者：Kevin D. Hesp、Rylan J. Lundgren、Mark Stradiotto

  DOI：10.1021/ja200009c

  日期：2011.4.13

  selective Pd-catalyzed mono-α-arylation of acetone employing aryl chlorides, bromides, iodides, and tosylates. The use of appropriately designed P,N-ligands proved to be the key to controlling the reactivity and selectivity. The reaction affords good yields with substrates containing a range of functional groups at modest Pd loadings using Cs(2)CO(3) as the base and employing acetone as both a reagent and

  我们报告了第一个使用芳基氯化物、溴化物、碘化物和甲苯磺酸盐选择性 Pd 催化的丙酮单α-芳基化的例子。使用适当设计的 P,N 配体被证明是控制反应性和选择性的关键。该反应使用 Cs(2)CO(3) 作为碱并使用丙酮作为试剂和溶剂，在适度的 Pd 负载下，使用含有一系列官能团的底物提供良好的产率。
• Secondary phenylethanol amines, processes for their preparation and their pharmaceutical application
  申请人：BEECHAM GROUP PLC

  公开号：EP0068669A1

  公开（公告）日：1983-01-05

  Compounds of formula (I) and salts and in vivo hydrolysable acyl derivatives thereof wherein R' is hydrogen or methyl; R2 is hydrogen or methyl; R3 is hydrogen, fluarine, chlorine, bromine, trifluoromethyl or C1-6 straight or branched chain alkyl; R4 is nitro, or optionally substitutec RS is hydrogen or C1-6 straight or branched chain alkyl; X is R6; R6 is hydrogen or C1-6 straight or branched chain alkyl; R7 is C1-6 straight or branched chain alkyl; R8 is hydrogen or C1-6 straight or branched chain alkyl; m is an integer from 1 to 6; p is an integer from 2 to 5; q is an integer from 0 to 2; provided that p + q is from 3 to 5; Y is R9 is hydrogen, C1-6 straight or branched alkyl or aralkyl consisting of a C2 or C10 aryl group and a C1-6 straight or branched chain alkylene group; any substituent on the group when present, being a carboxyl group or a salt, ester or amide thereof. have anti-obesity, and/or hypoglycaemic and/or antiin- flammation and/or platelet aggregation inhibiting activity.

  式(I)化合物 及其盐类和体内可水解酰基衍生物，其中 R' 是氢或甲基 R2 是氢或甲基 R3 是氢、氟、氯、溴、三氟甲基或 C1-6 直链或支链烷基； R4 是硝基、 或任选取代的C RS 是氢或 C1-6 直链或支链烷基； X 是 R6； R6 是氢或 C1-6 直链或支链烷基 R7 是 C1-6 直链或支链烷基 R8 是氢或 C1-6 直链或支链烷基； m 是 1 至 6 的整数； p 是 2 至 5 的整数 q 是 0 至 2 的整数； 条件是 p+q 为 3 至 5； Y 是 R9 是氢、C1-6 直链或支链烷基或由 C2 或 C10 芳基和 C1-6 直链或支链亚烷基组成的芳基； 基团上的任何取代基 基团上的任何取代基均为羧基或其盐、酯或酰胺。 具有抗肥胖和/或降血糖和/或抗炎和/或抑制血小板聚集活性。
• Preparation of a Highly Congested Carbazoyl-Derived P,N-Type Phosphine Ligand for Acetone Monoarylations
  作者：Wai Chung Fu、Zhongyuan Zhou、Fuk Yee Kwong

  DOI：10.1021/acs.organomet.6b00154

  日期：2016.5.23

  We report a newly developed carbazoyl-derived P,N-type phosphine ligand (L1) for the monoarylation of acetone with aryl chlorides. The proposed Pd(dba)(2)/L1 catalyst exhibited remarkable catalytic reactivity toward highly electron rich and sterically congested aryl chlorides, with catalyst loading as low as 0.1 mol % of Pd along with excellent chemoselectivity. A reaction rate study of the system using electronically diverse aryl chlorides determined the mechanisms regarding the rate-limiting steps in this reaction. The oxidative addition adduct of Pd-PhenCar-Phos with p-chlorotoluene showed the participation of N-Pd coordination in the metal complex. The isolated palladium complex C1 could be utilized as a precatalyst in the transformation and achieved performance comparable to that of the in situ generated palladium species.