2,2-(dimethyl)-6-[(triphenylphosphoranylidene)methyl]-4H-1,3-dioxin-4-one | 126491-93-8

• 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: 2,2-(dimethyl)-6-[(triphenylphosphoranylidene)methyl]-4H-1,3-dioxin-4-one
• 英文别名: 2,2-Dimethyl-6-[(triphenyl-lambda5-phosphanylidene)methyl]-1,3-dioxin-4-one；2,2-dimethyl-6-[(triphenyl-λ5-phosphanylidene)methyl]-1,3-dioxin-4-one
• CAS: 126491-93-8
• 化学式: C₂₅H₂₃O₃P
• 分子量: 402.43
• InChiKey: SSJAEWBWTJOPQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[(2R,3S)-2-formyl-1-(4-methoxyphenyl)-4-oxoazetidin-3-yl]-2-phenoxyacetamide 、 2,2-(dimethyl)-6-[(triphenylphosphoranylidene)methyl]-4H-1,3-dioxin-4-one 以76%的产率得到
  参考文献：
  名称：

  BODUROW, CHRISTINA;CARR, MICHAEL A., TETRAHEDRON LETT., 30,(1989) N1, C. 4081-4084

  摘要：

  DOI：

文献信息

• A mild four-carbon homologation of 4-formyl-azetidinones
  作者：Christina Bodurow、Michael A. Carr

  DOI：10.1016/s0040-4039(00)99327-4

  日期：1989.1

  A mild, four-carbon homologation of a 4-formyl-substituted azetidinone provides a route to compound I, a key intermediate in the total synthesis of the carbacephem antibiotics. The route features homologation with phosphorane IV and facile dioxenone opening in the final step of the sequence.

  4-甲酰基取代的氮杂环丁酮的轻度四碳同系物提供了通往化合物I的途径，化合物I是羧苄西林抗生素总合成中的关键中间体。该路线的特征是在序列的最后一步中与四氢呋喃IV和容易的二恶烯酮开口同源。
• 3-substituted carbacephems
  申请人：Pfizer Inc.

  公开号：US05716948A1

  公开（公告）日：1998-02-10

  A compound of formula (I) or a salt thereof, wherein R.sup.1 is hydrogen, methoxy or formamido; R.sup.2 is an acyl group, in particular that of an antibacterially active cephalosporin; CO.sub.2 R.sup.3 is a carboxy group or a carboxylate anion, or R.sup.3 is a readily removable carboxy protecting group or a pharmaceutically acceptable salt-forming group or in vivo hydrolysable ester group; R.sup.4 represents hydrogen or up to four substituents, which may be present on any of the carbon atoms in the ring system shown, selected from alkyl, alkenyl, alkynyl, alkoxy, hydroxy, halogen, amino, alkylamino, acylamino, dialkylamino, CO.sub.2 R, CONR.sub.2, SO.sub.2 NR.sub.2 where R is hydrogen or alkyl, aryl and heterocyclyl, which may be the same or different and wherein any R.sup.4 alkyl substituent is optionally substituted by one or more substituents selected from the list from which R.sup.4 is selected; Y is O, S, SO or SO.sub.2 ; and m is 1 or 2, a process for its preparation, use as an antibiotic and intermediates thereto.

  化合物的化学式（I）或其盐，其中R.sup.1是氢、甲氧基或甲酰胺基；R.sup.2是酰基，特别是一种具有抗菌活性的头孢菌素的酰基；CO.sub.2 R.sup.3是羧基或羧酸根离子，或者R.sup.3是易于去除的羧保护基或药用盐形成基或体内水解酯基；R.sup.4代表氢或最多四个取代基，这些取代基可以存在于所示环系的任何碳原子上，选自烷基、烯基、炔基、烷氧基、羟基、卤素、氨基、烷基氨基、酰基氨基、二烷基氨基、CO.sub.2 R、CONR.sub.2、SO.sub.2 NR.sub.2，其中R是氢或烷基、芳基和杂环基，可以相同也可以不同，并且其中任何R.sup.4烷基取代基可以选择性地被来自所选R.sup.4的列表中的一个或多个取代基取代；Y是O、S、SO或SO.sub.2；m为1或2，其制备方法，用作抗生素的用途及其中间体。
• A Rapid, Asymmetric Synthesis of the Decahydrofluorene Core of the Hirsutellones
  作者：S. David Tilley、Keith P. Reber、Erik J. Sorensen

  DOI：10.1021/ol802768p

  日期：2009.2.5

  A tandem ketene-trapping/Diels-Alder cyclization sequence was the pivotal transformation in an efficient, asymmetric synthesis of a decahydrofluorene tricyclic structure possessing eight stereogenic centers and key features of the hirsutellone class of antitubercular natural products. The hirsutellone-like beta-keto ester that was fashioned by this sequence (13 steps; 6% overall yield) demonstrated significant inhibitory activity against Mycobacterium tuberculosis. The mechanism of action of this antitubercular compound is not yet known.
• 3-SUBSTITUTED CARBACEPHEMS
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP0644886A1

  公开（公告）日：1995-03-29
• CARBACEPHALOSPORIN COMPOUND, THEIR PREPARATION AND USE
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP0689540A1

  公开（公告）日：1996-01-03