N-(4-hydroxyphenyl)azetidin-2-one | 1309606-48-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: N-(4-hydroxyphenyl)azetidin-2-one
• 英文别名: 1-(4-Hydroxyphenyl)azetidin-2-one
• CAS: 1309606-48-1
• 化学式: C₉H₉NO₂
• 分子量: 163.176
• InChiKey: ZFPKIQYKTUWFAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氮杂环丁酮 、 4-碘苯酚 在 copper(l) iodide 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以31%的产率得到N-(4-hydroxyphenyl)azetidin-2-one
  参考文献：
  名称：

  N-Arylazetidin-2-one的低温薯条重排合成2,3-二氢-4（1H）-喹诺酮和相应的4（1H）-喹诺酮*

  摘要：

  N型未取代的氮杂环丁烷-2-酮与相关的芳基卤化物或使用Mitsunobu环化方法，可通过Goldberg–Buchwald型铜催化的偶联反应容易地制备通式1的N-氮杂环丁烷-2-酮在三氟乙酸中于0–18°C进行重排，得到异构体2,3-二氢-4（1 H）-喹诺酮（2）。后一种化合物在1.0 M氢氧化钠/丙-2-醇水溶液中，在大约50 ℃下，用10％Pd / C脱氢。在82℃下提供了相应的4（1 H）-喹诺酮（3）。

  DOI：

  10.1071/ch10465

文献信息

• Process for preparing taxol-type compound from beta-lactam precursors
  申请人：WISCONSIN ALUMNI RESEARCH FOUNDATION

  公开号：EP0582469A2

  公开（公告）日：1994-02-09

  Taxol-type compounds are produced by coupling baccatin III-type compounds (and related alcohols) with chemoenzymatically produced β-lactam enantiomers. The β-lactam enantiomers are produced from racemic starting substituted β-lactams through lipase contacting to achieve either enantioselective hydrolysis or enantioselective transesterification (the latter with an added 1-substituted ethenyl acetate). Preferred β-lactam enantiomers are coupled to the C-13 hydroxyl of the starting baccatin III-type compounds which are derived from 10-deacetyl baccatin III. Certain of the β-lactam enantiomers are new as are taxol-type compounds produced by the coupling reaction.

  紫杉醇类似化合物是通过将紫杉醇Ⅲ型化合物（及相关醇类）与化学酶法产生的β-内酰胺对映体偶联而产生的。β-内酰胺对映体是通过脂肪酶接触来自手性起始取代β-内酰胺的光学异构体，以实现择优水解或选择性转酯化（后者加入了1-取代乙烯酸乙酯）。优选的β-内酰胺对映体与起始紫杉醇Ⅲ型化合物的C-13羟基耦合，后者是从10-去乙酰紫杉醇Ⅲ型化合物中得到的。某些β-内酰胺对映体是新的，由耦合反应产生的紫杉醇类似化合物也是新的。
• SULFUR-SUBSTITUTED AZETIDINONE COMPOUNDS USEFUL AS HYPOCHOLESTEROLEMIC AGENTS
  申请人：SCHERING CORPORATION

  公开号：EP0792264B1

  公开（公告）日：2002-02-27
• METHOD OF INHIBITING THE EXPRESSION OF A MULTI-DRUG RESISTANCE GENES AND INHIBITING THE PRODUCTION OF PROTEINS RESULTING FROM THE EXPRESSION OF SUCH GENES THEREBY ENHANCING THE EFFECTIVENESS OF CHEMOTHERAPEUTIC AGENTS TO TREAT CANCERS
  申请人：Forbes Medi-Tech Inc.

  公开号：EP1677803A2

  公开（公告）日：2006-07-12
• [EN] A METHOD OF INHIBITING THE EXPRESSION OF GENES WHICH MEDIATE CELLULAR CHOLESTEROL INFLUX IN ANIMAL CELLS AND INHIBITING THE PRODUCTION OF PROTEINS RESULTING FROM THE EXPRESSION OF SUCH GENES<br/>[FR] METHODE PERMETTANT D'INHIBER L'EXPRESSION DE GENES QUI INDUISENT L'INFLUX DE CHOLESTEROL CELLULAIRE DANS LES CELLULES ANIMALES ET D'INHIBER LA PRODUCTION DE PROTEINES ISSUES DE L'EXPRESSION DE CES GENES
  申请人：FORBES MEDI TECH INC

  公开号：WO2005042692A2

  公开（公告）日：2005-05-12

  The present invention provides, in one aspect, a method of inhibiting the expression of a gene which mediates cellular cholesterol influx in an animal cell which comprises administering to an animal an effective amount of at least one cholesterol absorption inhibitor. In another aspect, it provides a method of inhibiting the production of a protein expressed by a gene which mediates cellular cholesterol influx in an animal cell which comprises administering to an animal an effective amount of at least one cholesterol absorption inhibitor.
• [EN] METHOD OF INHIBITING THE EXPRESSION OF A MULTI-DRUG RESISTANCE GENES AND INHIBITING THE PRODUCTION OF PROTEINS RESULTING FROM THE EXPRESSION OF SUCH GENES THEREBY ENHANCING THE EFFECTIVENESS OF CHEMOTHERAPEUTIC AGENTS TO TREAT CANCERS<br/>[FR] METHODE DESTINEE A INHIBER L'EXPRESSION DE GENES DE MULTIRESISTANCE AUX MEDICAMENTS ET A INHIBER LA PRODUCTION DE PROTEINES RESULTANT DE L'EXPRESSION DE CES GENES EN VUE D'AMELIORER L'EFFICACITE D'AGENTS CHIMIOTHERAPEUTIQUES POUR LE TRAITEMENT DES CANCERS
  申请人：FORBES MEDI TECH INC

  公开号：WO2005030225A2

  公开（公告）日：2005-04-07

  The present invention provides, in one aspect, a method of inhibiting the expression of a multi-drug resistance gene in an animal cell which comprises administering to an animal an effective amount of at least one cholesterol absorption inhibitor. In another aspect, it provides a method of inhibiting the production of a protein expressed by a multi-drug resistance gene in an animal cell which comprises administering to an animal an effective amount of at least one cholesterol absorption inhibitor. In another aspect, the present invention provides a method of enhancing the effectiveness of a chemotherapeutic agent in an animal having cancer, which comprises administering to said animal an effective amount of the chemotherapeutic agent and at least one cholesterol absorption inhibitor. Further, there are provided compositions and kits for use in cancer treatment which comprise at least one chemotherapeutic agent and at least one cholesterol absorption inhibitor.