3-(2-Chlorophenyl)-1-cyclopropylprop-2-en-1-one | 1387581-92-1

• 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: 3-(2-Chlorophenyl)-1-cyclopropylprop-2-en-1-one
• CAS: 1387581-92-1
• 化学式: C₁₂H₁₁ClO
• 分子量: 206.672
• InChiKey: JPWHQTRJTXBIDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(2-Chlorophenyl)-1-cyclopropylprop-2-en-1-one 、 propargyl azide 在 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 24.5h， 以103 mg的产率得到4-(2-chlorophenyl)-2-cyclopropyl-5-methylpyridine
  参考文献：
  名称：

  Synthesis of Polysubstituted Pyridines via a One-Pot Metal-Free Strategy

  摘要：

  An efficient strategy for the one-pot synthesis of polysubstituted pyridines via a cascade reaction from aldehydes, phosphorus ylides, and propargyl azide is reported. The reaction sequence involves a Wittig reaction, a Staudinger reaction, an aza-Wittig reaction, a 6 pi-3-azatriene electrocyclization, and a 1,3-H shift. This protocol provides quick access to the polysubstituted pyridines from readily available substrates in good to excellent yields.

  DOI：

  10.1021/acs.orglett.5b02903
• 作为产物：
  描述：

  (2-环丙基-2-氧代乙基)三苯基-鏻溴化物 在 sodium hydroxide 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 2.0h， 生成 3-(2-Chlorophenyl)-1-cyclopropylprop-2-en-1-one
  参考文献：
  名称：

  Synthesis of Polysubstituted Pyridines via a One-Pot Metal-Free Strategy

  摘要：

  An efficient strategy for the one-pot synthesis of polysubstituted pyridines via a cascade reaction from aldehydes, phosphorus ylides, and propargyl azide is reported. The reaction sequence involves a Wittig reaction, a Staudinger reaction, an aza-Wittig reaction, a 6 pi-3-azatriene electrocyclization, and a 1,3-H shift. This protocol provides quick access to the polysubstituted pyridines from readily available substrates in good to excellent yields.

  DOI：

  10.1021/acs.orglett.5b02903

文献信息

• Synthesis and biological evaluation of novel pyrazoline derivatives as anti-inflammatory and antioxidant agents
  作者：Nadia A. Khalil、Eman M. Ahmed、Hala B. El-Nassan、Osama K. Ahmed、Ahmed M. Al-Abd

  DOI：10.1007/s12272-012-0606-9

  日期：2012.6

  A series of novel 5-aryl-3-cyclopropyl-4,5-dihydropyrazole derivatives 2a–p were synthesized via cyclization of chalcones 1a–h with thiosemicarbazide or semicarbazide HCl and evaluated as anti-inflammatory/antioxidant agents. The structures were confirmed by elemental analyses and spectral data. The free radical scavenging activity toward superoxide was determined. Their effect on hepatocytes viability and nitric oxide (NO) production in LPS-stimulated macrophages was also determined. The results showed that compounds 2e and 2n demonstrated the highest free-radical scavenging and anti-inflammatory activities, thus can be useful in the prevention of oxidative stress and inflammation-related disorders.

  通过查耳酮 1a-h 与硫代氨基脲或盐酸氨基脲的环化反应，合成了一系列新型 5-芳基-3-环丙基-4,5-二氢吡唑衍生物 2a-p，并将其作为抗炎/抗氧化剂进行了评估。元素分析和光谱数据证实了这些化合物的结构。还测定了它们对超氧化物的自由基清除活性。还测定了它们对肝细胞活力和 LPS 刺激巨噬细胞产生一氧化氮（NO）的影响。结果表明，化合物 2e 和 2n 具有最高的自由基清除活性和抗炎活性，因此可用于预防氧化应激和炎症相关疾病。
• PROCESS FOR THE PRODUCTION OF ANILINES
  申请人：Walter Harald

  公开号：US20090221855A1

  公开（公告）日：2009-09-03

  The present invention relates to a process for the preparation of compounds of formula wherein R 1 , R 2 and R 3 are each independently of the others hydrogen or C 1 -C 4 alkyl, by a) reacting compounds of formula (II) wherein R 1 , R 2 and R 3 are as defined for formula (I) and X is bromine or chlorine, with a compound of formula (III) wherein R 4 is hydrogen or C 1 -C 4 alkyl, in the presence of a base and catalytic amounts of at least one palladium complex compound, to form compounds of formula (IV) wherein R 1 , R 2 , R 3 and R 4 are as defined for formula (I), and b) converting those compounds, using a reducing agent, into compounds of formula (I).

  本发明涉及一种制备式化合物的方法，其中R1、R2和R3各自独立地为氢或C1-C4烷基，通过a)在碱和至少一种钯配合物催化剂存在下，将式（II）化合物与式（III）化合物反应，其中R1、R2和R3如式（I）所定义，X为溴或氯，形成式（IV）化合物，其中R1、R2、R3和R4如式（I）所定义；b)使用还原剂将这些化合物转化为式（I）化合物。
• PROCESS FOR THE PRODUCTION OF AROMATIC AMINDES IN THE PRESENCE OF A PALLADIUM COMPLEX COMPRISING A FERROCENYL BIPHOSPHINE LIGAND
  申请人：Walter Harald

  公开号：US20100256417A1

  公开（公告）日：2010-10-07

  The present invention relates to a process for the preparation of compounds of Formula (I), wherein R 1 is 1,3-dimethyl-butyl, 1,3,3-trimethyl-butyl or a group A 1 , wherein R 3 , R 4 and R 5 are each independently of the others hydrogen or C 1 -C 4 alkyl; and R 2 is hydrogen; or R 1 and R 2 together from the group A 2 , wherein R 6 , and R7 are each independently of the other hydrogen or C 1 -C 4 alkyl; or R 1 and R 2 together from the group A 3 , wherein R 5 and R 9 are each independently of the other hydrogen or C 1 -C 4 alkyl; wherein a compound of Formula (II) wherein R 1 and R 2 are as defined for formula I and X is bromine or chlorine, is reacted with ammonia in the presence of a base and a catalytic amount of at least one palladium complex compound, wherein the palladium complex compound comprises at least one ferrocenyl-biphosphine ligand.

  本发明涉及一种制备式（I）化合物的方法，其中R1为1,3-二甲基丁基、1,3,3-三甲基丁基或A1基团，其中R3、R4和R5各自独立地为氢或C1-C4烷基；R2为氢；或者R1和R2一起形成A2基团，其中R6和R7各自独立地为氢或C1-C4烷基；或者R1和R2一起形成A3基团，其中R5和R9各自独立地为氢或C1-C4烷基；其中化合物式（II）其中R1和R2如式（I）所定义，X为溴或氯，在碱和至少一种钯配合物催化剂的存在下与氨反应，其中钯配合物包括至少一种二茂铁双膦配体。
• PROCESS FOR THE PRODUCTION OF AROMATIC AMINES IN THE PRESENCE OF A PALLADIUM COMPLEX COMPRISING A FERROCENYL BIPHOSPHINE LIGAND
  申请人：Syngenta Participations AG

  公开号：EP2066617A1

  公开（公告）日：2009-06-10
• US7737301B2
  申请人：——

  公开号：US7737301B2

  公开（公告）日：2010-06-15