(4S)-1-(4-fluorophenyl)-4-(hydroxyphenyl)azetidine-2-one | 452068-48-3

• 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: (4S)-1-(4-fluorophenyl)-4-(hydroxyphenyl)azetidine-2-one
• 英文别名: 1-(4-fluorophenyl)-4(S)-(4-hydroxyphenyl)-azetidin-2-one；(4S)-1-(4-fluorophenyl)-4-(4-hydroxyphenyl)azetidin-2-one
• CAS: 452068-48-3
• 化学式: C₁₅H₁₂FNO₂
• 分子量: 257.264
• InChiKey: KNVHOHPTYTUXBZ-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S)-1-(4-fluorophenyl)-4-(hydroxyphenyl)azetidine-2-one 、 trifluoromethanesulfonic acid anhydride 在 吡啶 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以90.7%的产率得到4-[[(2S)-1-(4-fluorophenyl)-4-oxoazetidine-2-yl]phenyl]trifluoromethanesulfonate
  参考文献：
  名称：

  BETA-LACTAM COMPOUNDS, PROCESS FOR REPODUCING THE SAME AND SERUM CHOLESTEROL-LOWERING AGENTS CONTAINING THE SAME

  摘要：

  公开号：

  EP1362855B1
• 作为产物：
  描述：

  (S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)azetidin-2-one 在 5%-palladium/activated carbon 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 9.0h， 以91.9%的产率得到(4S)-1-(4-fluorophenyl)-4-(hydroxyphenyl)azetidine-2-one
  参考文献：
  名称：

  BETA-LACTAM COMPOUNDS, PROCESS FOR REPODUCING THE SAME AND SERUM CHOLESTEROL-LOWERING AGENTS CONTAINING THE SAME

  摘要：

  公开号：

  EP1362855B1

文献信息

• Process for the preparation of 1-(4-fluorophenyl)-4(S)-(4-hydroxyphenyl)-azetidin-2-one
  申请人：——

  公开号：US20040254369A1

  公开（公告）日：2004-12-16

  A process for preparing a compound of the formula 1 comprising: (a) formation of 3(S)-(4-hydroxyphenyl)-3-methanesulfonyloxy-propionic acid methyl ester compound of the formula 2 (b) cyclization of the product of Step (a) with 4-fluoroaniline to yield 1-(4-fluorophenyl)-4(S)-(4-hydroxyphenyl)-azetidin-2-one.

  制备化合物的方法，包括：(a)形成式1的3(S)-(4-羟基苯基)-3-甲磺氧基丙酸甲酯化合物的步骤；(b)将步骤(a)的产物与4-氟苯胺环化，得到1-(4-氟苯基)-4(S)-(4-羟基苯基)-氮杂环丙酮的步骤。
• Process for the preparation of chiral azetidinones
  申请人：Framroze Patel Bomi

  公开号：US20070129540A1

  公开（公告）日：2007-06-07

  Processes for preparing compounds of formula I are disclosed comprising the steps of: (a) forming of chiral propionic acid ester compounds of formula V. (b) reacting compounds of formula V with aniline compounds to yield compounds of formula I

  公开了制备式I化合物的过程，包括以下步骤：(a)形成式V手性丙酸酯化合物。(b)将式V化合物与苯胺化合物反应，得到式I化合物。
• Beta-lactam compounds process for reproducing the same and serum cholesterol-lowering agents containing the same
  申请人：——

  公开号：US20040063929A1

  公开（公告）日：2004-04-01

  Novel &bgr;-lactam compounds represented by the following general formula (I) or pharmaceutically acceptable salts thereof which are useful as serum cholesterol-lowering agents: (I) wherein A 1 , A 3 and A 4 represent each hydrogen, halogen, C 1-5 alkyl, C 1-5 alkoxy, —COOR 1 , a group represented by the following general formula (b): (b) wherein R 1 represents hydrogen or C 1-5 alkyl, or a group represented by the following general formula (a): (a) wherein R 2 represents —CH 2 OH, —CH 2 OC(O)—R 1 or —CO 2 —R 1 ; R 3 represents —OH or —OC(O)—R 1 ; R 4 represents —(CH 2 ) k R 5 (CH 2 ) l — wherein k and l are each 0 or an integer of 1 or above provided k+l is an integer of not more than 10; and R 5 represents a single bond, —CH═CH—, —OCH 2 —, carbonyl or —CH(OH)—; provided that at least one of A 1 , A 3 and A 4 is a group represented by the above formula (a); A 2 represents C 1-5 alkyl, C 1-5 alkoxy, C 1-5 alkenyl, C 1-5 hydroxyalkyl or C 1-5 carbonylalkyl; and n, p, q and r are each an integer of 0, 1 or 2.

  以下一般式(I)所表示的新型&bgr;-内酰胺化合物或其药学上可接受的盐，可用作血清降胆固醇剂：其中，A1、A3和A4分别表示氢、卤素、C1-5烷基、C1-5烷氧基、—COOR1、由以下一般式(b)所表示的基团：(b)其中R1表示氢或C1-5烷基，或由以下一般式(a)所表示的基团：(a)其中R2表示—CH2OH、—CH2OC(O)—R1或—CO2—R1；R3表示—OH或—OC(O)—R1；R4表示—(CH2)kR5(CH2)l—，其中k和l分别为0或1以上的整数，且k+l为不超过10的整数；R5表示单键、—CH═CH—、—OCH2—、羰基或—CH(OH)—，但至少其中一个A1、A3和A4为上述一般式(a)所表示的基团；A2表示C1-5烷基、C1-5烷氧基、C1-5烯基、C1-5羟基烷基或C1-5羰基烷基；n、p、q和r分别为0、1或2的整数。
• Use of inhibitors of scavenger receptor class proteins for the treatment of infectious diseases
  申请人：Cenix Bioscience GmbH

  公开号：EP1832283A1

  公开（公告）日：2007-09-12

  The present invention relates to the use of inhibitors of scavenger receptor class proteins, in particular ScarB1 for the production of a medicament for treatment of and/or prophylaxis against infections, involving liver cells and/or hematopoietic cells, in particular malaria.

  本发明涉及使用清道夫受体类蛋白，特别是 ScarB1 的抑制剂来生产治疗和/或预防涉及肝细胞和/或造血细胞，特别是疟疾的感染的药物。
• METHOD FOR PREPARING AZETIDINONE COMPOUND AND INTERMEDIATE OF AZETIDINONE COMPOUND
  申请人：Zhejiang Hisun Pharmaceutical Co., Ltd.

  公开号：EP3153496A1

  公开（公告）日：2017-04-12

  Disclosed is a new method for preparing an azetidinone compound represented by formula (I). The carboxylic ketoester represented by formula (II) serves as the raw material and is subjected to Grignard addition, stereoselective dehydration, ester group reduction, hydroxyl group protection, addition with imine after condensation with a chiral auxiliary, cyclization and deprotection to obtain the compound represented by formula (I). The present invention has advantages of easily available raw material, a few synthetic steps, simple operation, high yield, good stereoselectivity and low cost, and can be used for industrial production.

  本发明公开了一种制备式 (I) 所代表的氮杂环丁酮化合物的新方法。以式（II）代表的羧基酮酯为原料，经过格氏加成、立体选择性脱水、酯基还原、羟基保护、与手性助剂缩合后与亚胺加成、环化和脱保护得到式（I）代表的化合物。本发明具有原料易得、合成步骤少、操作简单、收率高、立体选择性好、成本低等优点，可用于工业生产。