1-(4-dimethylamino-phenyl)-penta-1,4-dien-3-one | 916750-27-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 1-(4-dimethylamino-phenyl)-penta-1,4-dien-3-one
• 英文别名: para-(dimethylamino)styryl vinyl ketone；1-[4-(Dimethylamino)phenyl]penta-1,4-dien-3-one；(1E)-1-[4-(dimethylamino)phenyl]penta-1,4-dien-3-one
• CAS: 916750-27-1
• 化学式: C₁₃H₁₅NO
• 分子量: 201.268
• InChiKey: LMLZWNWRRHRVDY-JXMROGBWSA-N

物化性质

• 熔点：
  95-96 °C
• 沸点：
  349.0±35.0 °C(Predicted)
• 密度：
  1.039±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-dimethylamino-phenyl)-penta-1,4-dien-3-one 、 苯二甲酰亚氨基乙醛 在 Bis(1,5-cyclooctadiene)rhodium(I) hexafluoroantimonate (2-Fur)3P 、 氢气 、 lithium carbonate 作用下， 以 二氯甲烷 为溶剂， 25.0 ℃ 、101.32 kPa 条件下， 反应 12.0h， 以81%的产率得到2-[6-(4-dimethylamino-phenyl)-2-hydroxy-3-methyl-4-oxo-hex-5-enyl]-isoindole-1,3-dione
  参考文献：
  名称：

  Reductive Aldol Coupling of Divinyl Ketones via Rhodium-Catalyzed Hydrogenation:  syn-Diastereoselective Construction of β-Hydroxyenones

  摘要：

  Catalytic hydrogenation of divinyl ketones 1a and 1e in the presence of diverse aldehydes 2a-e at ambient temperature and pressure using cationic rhodium catalysts ligated by tri-2-furyl phosphine enables formation of aldol products 3a-e and 5a-e, respectively, with high levels of syn diastereoselection. Through an assay of counterions (Rh(COD)(2)X), Rh(COD)(2)SbF6 is identified as the optimum precatalyst for reductive aldol couplings of this type. For para-substituted styryl vinyl ketones 1b-e, a progressive increase in isolated yield is observed for electron-releasing para substituents.

  DOI：

  10.1021/ol0624023
• 作为产物：
  描述：

  3-(4-dimethylamino-phenyl)-propenal 在 manganese(IV) oxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 1-(4-dimethylamino-phenyl)-penta-1,4-dien-3-one
  参考文献：
  名称：

  Reductive Aldol Coupling of Divinyl Ketones via Rhodium-Catalyzed Hydrogenation:  syn-Diastereoselective Construction of β-Hydroxyenones

  摘要：

  Catalytic hydrogenation of divinyl ketones 1a and 1e in the presence of diverse aldehydes 2a-e at ambient temperature and pressure using cationic rhodium catalysts ligated by tri-2-furyl phosphine enables formation of aldol products 3a-e and 5a-e, respectively, with high levels of syn diastereoselection. Through an assay of counterions (Rh(COD)(2)X), Rh(COD)(2)SbF6 is identified as the optimum precatalyst for reductive aldol couplings of this type. For para-substituted styryl vinyl ketones 1b-e, a progressive increase in isolated yield is observed for electron-releasing para substituents.

  DOI：

  10.1021/ol0624023

文献信息

• CURCUMIN, ANALOGUES OF CURCUMIN AND NOVEL USES THEREOF
  申请人：RESEARCH DEVELOPMENT FOUNDATION

  公开号：EP0738143A1

  公开（公告）日：1996-10-23
• [EN] CURCUMIN, ANALOGUES OF CURCUMIN AND NOVEL USES THEREOF<br/>[FR] CURCUMINE, SES ANALOGUES ET LEURS NOUVELLES UTILISATIONS
  申请人：——

  公开号：WO1995018606A1

  公开（公告）日：1995-07-13

  [EN] The present invention provides novel methods for the treatement of pathological cell proliferative diseases. The novel methods of the present invention comprise administration to an animal of a pharmacologically effective dose of curcumin or an analogue thereof. The present invention also provides a novel method of inhibiting the activity of phosphorylase kinase and tyrosine kinase and a novel method of treating cell proliferative diseases by administering a pharmacologically effective dose of a flavonoid.
  [FR] Nouvelles méthodes de traitement de maladies caractérisées par la prolifération pathologique de cellules, consistant à administrer à un animal une dose à efficacité pharmacologique de curcumine ou de l'un de ses analogues, nouvelle méthode d'inhibition de l'activité de la phosphorylase kinase et de la tyrosine kinase, et nouvelle méthode de traitement des maladies caractérisées par la prolifération pathologique de cellules consistant à administrer une dose à efficacité pharmacologique de flavonoïde.
• [EN] CURCUMIN ANALOGUES FOR TREATING CANCER<br/>[FR] ANALOGUES DE CIRCUMINE DESTINES AU TRAITEMENT DU CANCER
  申请人：——

  公开号：WO2001040188A9

  公开（公告）日：2002-07-25

  [EN] The present invention is directed to curcumin analogs (I), wherein Y is OH, halogen, or CF3; Z is H, OH, OR1, halogen, or CF3; X1 and X2 are independently C or N; and A is as defined in the application; exhibiting anti-tumor and anti-angiogenic properties, pharmaceutical formulations including such compounds and methods of using such compounds.
  [FR] La présente invention concerne des analogues de circumine (I) dans laquelle Y est OH, halogène ou CF3; Z est H, OH, OR1, halogène ou CF3; X1 et X2 sont indépendamment C ou N et A est défini dans l'application; ces analogues ont des propriétés anti-angiogéniques et antitumorales. L'invention concerne aussi des formulation comprenant ces composés et des procédés d'utilisation correspondants.
• Reductive Aldol Coupling of Divinyl Ketones via Rhodium-Catalyzed Hydrogenation:  syn-Diastereoselective Construction of β-Hydroxyenones
  作者：Soo Bong Han、Michael J. Krische

  DOI：10.1021/ol0624023

  日期：2006.11.1

  Catalytic hydrogenation of divinyl ketones 1a and 1e in the presence of diverse aldehydes 2a-e at ambient temperature and pressure using cationic rhodium catalysts ligated by tri-2-furyl phosphine enables formation of aldol products 3a-e and 5a-e, respectively, with high levels of syn diastereoselection. Through an assay of counterions (Rh(COD)(2)X), Rh(COD)(2)SbF6 is identified as the optimum precatalyst for reductive aldol couplings of this type. For para-substituted styryl vinyl ketones 1b-e, a progressive increase in isolated yield is observed for electron-releasing para substituents.