1-(2'-methyl-7'-quinolyl)-2-propanone | 1398566-01-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-(2'-methyl-7'-quinolyl)-2-propanone
• 英文别名: 1-(2-methylquinolin-7-yl)propan-2-one
• CAS: 1398566-01-2
• 化学式: C₁₃H₁₃NO
• 分子量: 199.252
• InChiKey: IJNYMBXSRNZGEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  7-氯喹哪啶 、 丙酮 在 bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)] 、 [2-二环己基膦基-3-甲氧基-N-甲基-N-苯基苯胺 、 caesium carbonate 作用下， 反应 12.0h， 以81%的产率得到1-(2'-methyl-7'-quinolyl)-2-propanone
  参考文献：
  名称：

  Zheda-Phos用于丙酮与芳基氯的一般α-单芳基化

  摘要：

  已经开发出一种新的，易于获得的，对空气稳定的单膦配体Zheda-Phos，用于丙酮与芳基氯化物的丙酮催化的一般的，高效的单芳基化反应。与芳基氯的反应速率是一阶依赖性的。

  DOI：

  10.1002/adsc.201300207

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。
• DIALKYL(2-ALKOXY-6-AMINOPHENYL)PHOSPHINE, THE PREPARATION METHOD AND USE THEREOF
  申请人：Ma Shengming

  公开号：US20140309422A1

  公开（公告）日：2014-10-16

  The present invention relates to the compound of dialkyl(2-alkoxy-6-aminophenyl)phosphine and the preparation method thereof and the application in the palladium catalyzed coupling reactions of aryl chloride and ketone. The dialkyl(2-alkoxy-6-aminophenyl)phosphine of the present invention could coordinate with the palladium catalyst to highly selectively activate the inert carbon-chlorine bond, and to catalyze direct arylation reaction in the α-position of ketones to produce corresponding coupling compounds. The preparation method of the present invention is a simple one-step method which produces the air-stable dialkyl(2-alkoxy-6-aminophenyl)phosphine. Compared with the synthetic routes of ligands to be used in the activation of carbon-chlorine bonds in the prior arts, the preparation method of the present invention has the advantages of short route and easy operation.

  本发明涉及二烷基（2-烷氧基-6-氨基苯基）膦化合物及其制备方法，以及在钯催化芳基氯化物和酮的偶联反应中的应用。本发明的二烷基（2-烷氧基-6-氨基苯基）膦化合物能够与钯催化剂配位，高度选择性地活化惰性碳-氯键，并催化酮的α位直接芳基化反应，生成相应的偶联化合物。本发明的制备方法是一种简单的一步法，可制备出稳定于空气中的二烷基（2-烷氧基-6-氨基苯基）膦化合物。与先前用于活化碳-氯键的配体的合成路线相比，本发明的制备方法具有路线短、操作简便的优点。
• Organic Base Enabled Nickel‐Catalyzed Mono‐α‐Arylation of Feedstock Solvents
  作者：Joshua W. M. MacMillan、Ryan T. McGuire、Mark Stradiotto

  DOI：10.1002/chem.202200764

  日期：2022.5.16

  We report on our successful development of the first metal-catalyzed mono-α-arylation of carbonyl compounds employing a soluble organic base. The scope of these Ni/DalPhos-catalyzed transformations encompasses a range of (hetero)aryl halides (Cl, Br, I) and phenol-derived electrophiles (sulfonates, carbonates, carbamates, sulfamates), including active pharmaceutical ingredients (chloroquine, clozapine)

  我们报告了我们使用可溶性有机碱成功开发了第一个金属催化的羰基化合物单α-芳基化。这些 Ni/DalPhos 催化转化的范围包括一系列（杂）芳基卤化物（Cl、Br、I）和苯酚衍生的亲电子试剂（磺酸盐、碳酸盐、氨基甲酸盐、氨基磺酸盐），包括活性药物成分（氯喹、氯氮平） ，与通常有问题的原料小分子底物丙酮、二甲基乙酰胺结合，并首次与任何金属催化剂/碱、乙酸乙酯结合。
• 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.
• US9243011B2
  申请人：——

  公开号：US9243011B2

  公开（公告）日：2016-01-26