(3R-trans)-3-phenoxyacetylamino-4-phenylsulfonyl-2-azetidinone | 88002-47-5

• 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: (3R-trans)-3-phenoxyacetylamino-4-phenylsulfonyl-2-azetidinone
• 英文别名: N-[(2S,3R)-2-(benzenesulfonyl)-4-oxoazetidin-3-yl]-2-phenoxyacetamide
• CAS: 88002-47-5
• 化学式: C₁₇H₁₆N₂O₅S
• 分子量: 360.39
• InChiKey: GUZWHKAVYLVYBW-WBVHZDCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R-trans)-3-phenoxyacetylamino-4-phenylsulfonyl-2-azetidinone 在 吡啶 、 盐酸 、 二甲基硫 、 4 A molecular sieve 、 四氯化锡 、 臭氧 、 lithium tri-t-butoxyaluminum hydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 19.75h， 生成 p-nitrobenzyl 7β-[(phenoxyacetyl)amino]-3-hydroxy-1-carba-1-dethia-3-cephem-4-carboxylate
  参考文献：
  名称：

  Halide-Terminated N-Acyliminium Ion−Alkyne Cyclizations:  A New Construction of Carbacephem Antibiotics

  摘要：

  A series of 4-(3-alkynyl)azetidinones 13 was prepared from 4-(phenylsulfonyl)azetidine-2-one (9) and isopropyl glyoxylate hydrate. The 3-pentynyl (13a) and 4-phenyl-3-butynyl (13b) azetidinone acetates underwent 6-exo cyclization when treated with 3 equiv of SnCl4 at 0 degrees C to provide 3-(1-chloroalkylidene)carbacephems 15a (65%) and 15b (33%) respectively. In contrast, the 5-butynyl (13d) and 4-(trimethylsilyl)-3-butynyl (13c) azetidinone acetates under ent 7-endo cyclization under similar conditions to give 1-azabicyclo[5.2.0]nonenes 14a (11%) and 14b (71%), respectively. Beginning with penicillin degradation product 18, the more elaborate 3-pentynyl azetidinone cyclization substrate 27 was prepared in seven steps. Exposure to 27 to 3 equiv of SnCl4 in CH2Cl2 at 0 degrees C for 6 h, followed by allowing the reaction mixture to warm to rt, provided the desired 3-(1-chloroethylidene)carbacephem 28 in 60% yield and high (>99%) enantiometric purity. Cleavage of the chloroethylidene group of 28 with ozone gave 3-hydroxy carbacephem 29 in 77% yield. Since this intermediate has been converted in three steps to loracarbef (3), a new formal total synthesis of this carbacephem antiboitic was concluded.

  DOI：

  10.1021/jo971433w
• 作为产物：
  描述：

  sodium benzenesulfonate 、 3-phenoxyacetamido-4-acetoxy-2-azetidinone 以 N,N-二甲基甲酰胺 为溶剂， 以81%的产率得到(3R-trans)-3-phenoxyacetylamino-4-phenylsulfonyl-2-azetidinone
  参考文献：
  名称：

  从青霉素立体选择性合成顺式取代的氮杂环丁酮：洛拉卡培的正式全合成

  摘要：

  描述了合成在4-位​​带有碳-碳键的手性氮杂环丁酮的新方法。该制备涉及甲硅烷基化的4-苯基磺酰基氮杂环丁酮的立体选择性烷基化还原。正式的劳拉卡帕夫全合成方法证明了该方法的实用性。

  DOI：

  10.1016/s0040-4039(00)93376-8

文献信息

• 4-Norbornyl-sulfonyl azetidinone intermediates and process for preparing
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04421686A1

  公开（公告）日：1983-12-20

  Compounds having the formula ##STR1## can be prepared by reacting a compound having the formula ##STR2## with a Grignard reagent having the formula R.sub.3 -Mg-X.sub.1 , wherein R.sub.1 is phenylacetyl or phenoxyacetyl; R.sub.2 is a not readily enolyzable alkyl group, aryl or norbornyl; R.sub.3 is alkyl, alken-1-yl, alkyn-1-yl, 2-phenylethenyl, 2-phenylethynyl, aryl or arylalkyl; X.sub.1 is bromine or chlorine. (3R-cis)-3-Acylamino-4-norbornylsulfonyl-2-azetidinones are novel compounds that form an integral part of this invention.

  具有公式##STR1##的化合物可以通过将具有公式##STR2##的化合物与具有公式R.sub.3-Mg-X.sub.1的Grignard试剂反应制备，其中R.sub.1为苯乙酰基或苯氧乙酰基；R.sub.2为不易使烯醇化的烷基、芳基或莫反烯基；R.sub.3为烷基、烯基、炔基、2-苯乙烯基、2-苯乙炔基、芳基或芳基烷基；X.sub.1为溴或氯。(3R-cis)-3-酰基氨基-4-莫反烯基磺酰基-2-氮杂环己酮是本发明的新化合物的一部分。
• Novel intermediates and process for preparing (S)-3-acylamino-4-substituted-2-azetidinones
  申请人：E.R. Squibb & Sons, Inc.

  公开号：EP0080942A1

  公开（公告）日：1983-06-08

  Compounds having the formula can be prepared by reacting a compound having the formula with a Grignard reagent having the formula wherein R, is phenylacetyl or phenoxyacetyl; R2 is a not readily enolyzable alkyl group, aryl or norbornyl; R3 is alkyl, alken-1-yl, alkyn-1-yl, 2-phenylethenyl, 2-phenylethynyl, aryl or arylalkyl; X, is bromine or chlorine. (3R-cis)-3-Acylamino-4-norbornylsulfonyl-2-azetidinones are novel compounds that form an integral part of this invention.

  具有式子的化合物可通过使具有式子的化合物与具有式子的格氏试剂反应来制备 其中 R 是苯乙酰基或苯氧基乙酰基；R2 是不易分解的烷基、芳基或降冰片基；R3 是烷基、烯-1-基、炔-1-基、2-苯基乙烯基、2-苯基乙炔基、芳基或芳烷基；X 是溴或氯。 (3R-顺式)-3-酰氨基-4-降冰片基磺酰基-2-氮杂环丁酮是构成本发明组成部分的新型化合物。
• Process for preparing 4-substituted azetidinones
  申请人：ELI LILLY AND COMPANY

  公开号：EP0419215A2

  公开（公告）日：1991-03-27

  A process for preparing 3-4-cis-β,β-(4)-substituted and 3-4-trans,β,α-(4)-substituted azetidinones is provided. Also provided are novel 4,4-disubstituted azetidinones.

  提供了一种制备 3-4-顺式-β,β-(4)-取代的氮杂环丁酮和 3-4-反式-β,α-(4)-取代的氮杂环丁酮的工艺。此外，还提供了新型 4,4-二取代氮杂环丁酮。
• US4421686A
  申请人：——

  公开号：US4421686A

  公开（公告）日：1983-12-20
• US5106475A
  申请人：——

  公开号：US5106475A

  公开（公告）日：1992-04-21