N-t-butyldimethylsilyl-3-trimethylsilyloxyazetidin-2-one | 137627-17-9

• 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-t-butyldimethylsilyl-3-trimethylsilyloxyazetidin-2-one
• 英文别名: 1-(tert-butyldimethylsilyl)-3-<(trimethylsilyl)oxy>-2-azetidinone；1-[Tert-butyl(dimethyl)silyl]-3-trimethylsilyloxyazetidin-2-one
• CAS: 137627-17-9
• 化学式: C₁₂H₂₇NO₂Si₂
• 分子量: 273.523
• InChiKey: NJZCPQOEBOIONV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-t-butyldimethylsilyl-3-trimethylsilyloxyazetidin-2-one 在 lithium diisopropyl amide 作用下， 反应 3.0h， 生成 (3RS,3'S,4'E)-1-(tert-butyldimethylsilyl)-3-<3'-<(benzyloxycarbonyl)amino>hex-4'-enyl>-3-hydroxy-2-oxoazetidine
  参考文献：
  名称：

  Enantiospecific synthesis of (-)-tabtoxinine .beta.-lactam

  摘要：

  A convergent, 10-step synthesis of optically active tabtoxinine beta-lactam [(-)-1] has been described. Key features of the synthetic route include (1) preparation of a new gamma-cation amino acid synthon, (-)-4, and its use as an electrophile (3 --> 11); (2) the one-pot conversion of methyl sulfide 11 to the Cbz-protected amine 12 via stereoselective sulfilimine rearrangement; and (3) chemoselective lactone ring opening in spiro lactam 15a. Synthons (-)-4 and 3 are available on a semipreparative scale.

  DOI：

  10.1021/jo00027a024
• 作为产物：
  描述：

  1-[tert-butyl(dimethyl)silyl]azetidin-2-one 在 MoO5*pyridine*HMPA 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 N-t-butyldimethylsilyl-3-trimethylsilyloxyazetidin-2-one
  参考文献：
  名称：

  N-叔丁基二甲基甲硅烷基-3-三甲基甲硅烷基氧氮杂环丁烷-2-酮的制备和烷基化

  摘要：

  标题β-内酰胺（6）由市售的2-氮杂环丁酮（9）分三步制备（总收率50％），可以用多种亲电试剂有效地烷基化。

  DOI：

  10.1039/c39890001448

文献信息

• Preparation and alkylation of N-t-butyldimethylsilyl-3-trimethylsilyloxyazetidin-2-one
  作者：Roland E. Dolle、Mark J. Hughes、Chun-Sing Li、Lawrence I. Kruse

  DOI：10.1039/c39890001448

  日期：——

  The title β-lactam (6) is prepared in three steps from commercially available 2-azetidinone (9)(50% overall yield) and can be efficiently alkylated with a variety of electrophiles.

  标题β-内酰胺（6）由市售的2-氮杂环丁酮（9）分三步制备（总收率50％），可以用多种亲电试剂有效地烷基化。
• Dolle Roland E., McNair David, Hughes Mark J., Kruse Lawrence I., Eggelst+, J. Med. Chem., 35 (1992) N 26, S 4875-4884
  作者：Dolle Roland E., McNair David, Hughes Mark J., Kruse Lawrence I., Eggelst+

  DOI：——

  日期：——
• ATP-citrate-lyase as a target for hypolipidemic intervention. Sulfoximine and 3-hydroxy-.beta.-lactam containing analogs of citric acid as potential tight-binding inhibitors
  作者：Roland E. Dolle、David McNair、Mark J. Hughes、Lawrence I. Kruse、Drake Eggelston、Barbara A. Saxty、Timothy N. C. Wells、Pieter H. E. Groot

  DOI：10.1021/jm00104a014

  日期：1992.12

  Citric acid analogues (+/-)-12a,b and (+/-)-17a,b, where one of the primary carboxylates has been replaced by a sulfoximinoyl and a 3-(3-hydroxy-beta-lactamyl) moiety, respectively, have been synthesized and evaluated as inhibitors of ATP-citrate lyase. The design of these inhibitors was based on methionine sulfoximine and tabtoxinine beta-lactam, potent, tight-binding inhibitors of glutamine synthetase. Both ATP-citrate lyase and glutamine synthetase employ phosphate-carboxylate anhydrides as a method for carboxylate activation during catalysis. Only one diastereomer, (+/-)-12a, displayed weak, reversible inhibition, while the remaining citrate analogues (+/-)-12b and (+/-)-17a,b were inactive against the lyase. No time-dependent inactivation of the enzyme was observed.
• Enantiospecific synthesis of (-)-tabtoxinine .beta.-lactam
  作者：Roland E. Dolle、Chun Sing Li、Riccardo Novelli、Lawrence I. Kruse、Drake Eggleston

  DOI：10.1021/jo00027a024

  日期：1992.1

  A convergent, 10-step synthesis of optically active tabtoxinine beta-lactam [(-)-1] has been described. Key features of the synthetic route include (1) preparation of a new gamma-cation amino acid synthon, (-)-4, and its use as an electrophile (3 --> 11); (2) the one-pot conversion of methyl sulfide 11 to the Cbz-protected amine 12 via stereoselective sulfilimine rearrangement; and (3) chemoselective lactone ring opening in spiro lactam 15a. Synthons (-)-4 and 3 are available on a semipreparative scale.