N-methoxy-N-methyl-6,7,13-O-tris(trimethylsilyl)monoamide | 136380-26-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-methoxy-N-methyl-6,7,13-O-tris(trimethylsilyl)monoamide
• 英文别名: (E)-4-[(2S,3S,4R,5S)-3,4-bis(trimethylsilyloxy)-5-[[(2S,3S)-3-[(2R,3S)-3-trimethylsilyloxybutan-2-yl]oxiran-2-yl]methyl]oxan-2-yl]-N-methoxy-N,3-dimethylbut-2-enamide
• CAS: 136380-26-2
• 化学式: C₂₈H₅₇NO₇Si₃
• 分子量: 604.02
• InChiKey: XRXFTTTXOABMKN-DIVZENRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.83
• 重原子数：
  39
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  79
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-methoxy-N-methyl-6,7,13-O-tris(trimethylsilyl)monoamide 在 4-二甲氨基吡啶 叔丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (R)-3-Methoxy-6-(1-{(2S,3S,4R,5S)-5-[(2S,3S)-3-((1R,2S)-1-methyl-2-trimethylsilanyloxy-propyl)-oxiranylmethyl]-3,4-bis-trimethylsilanyloxy-tetrahydro-pyran-2-ylmethyl}-vinyl)-5,6-dihydro-[2]pyrindin-7-one
  参考文献：
  名称：

  Preparation of E-(2-substituted-1-methylethylidene)indanones derived from monic acid

  摘要：

  Alkylation of the lithium dienolate of the monic acid hydroxamate (3) with o-bromo(bromomethyl) benzene or heteroaromatic derivatives gave alpha-alkylated products (5). This alkylation procedure wa surprisingly catalysed by 4-dimethylaminopyridine. Metal-halogen exchange with t-butyl lithium occurred with concomitant intramolecular cyclisation to give a mixture of the deconjugated ketones (6). Reconjugation with potassium t-butoxide stereoselectively produced with the E-isomer (7). Deprotection gave the monic acid derived ketone (1).

  DOI：

  10.1016/s0040-4039(00)73095-4
• 作为产物：
  描述：

  monic acid A 在 4-二甲氨基吡啶 三乙胺 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 N-methoxy-N-methyl-6,7,13-O-tris(trimethylsilyl)monoamide
  参考文献：
  名称：

  Preparation of E-(2-substituted-1-methylethylidene)indanones derived from monic acid

  摘要：

  Alkylation of the lithium dienolate of the monic acid hydroxamate (3) with o-bromo(bromomethyl) benzene or heteroaromatic derivatives gave alpha-alkylated products (5). This alkylation procedure wa surprisingly catalysed by 4-dimethylaminopyridine. Metal-halogen exchange with t-butyl lithium occurred with concomitant intramolecular cyclisation to give a mixture of the deconjugated ketones (6). Reconjugation with potassium t-butoxide stereoselectively produced with the E-isomer (7). Deprotection gave the monic acid derived ketone (1).

  DOI：

  10.1016/s0040-4039(00)73095-4

文献信息

• Chemistry of Pseudomonic Acid. Part 16. Aryl and Heteroaryl Ketone Derivatives of Monic Acid.
  作者：ANGELA ABSON、NIGEL J. P. BROOM、PHILIPPA A. COATES、JOHN S. ELDER、ANDREW K. FORREST、PETER C. T. HANNAN、AMANDA J. HICKS、PETER J. O'HANLON、NICKY D. MASSON、NEIL D. PEARSON、JEAN E. PONS、JENNIFER M. WILSON

  DOI：10.7164/antibiotics.49.390

  日期：——

  The synthesis, antibacterial activities, murine pharmacokinetic and infection model data for a range of aryl and heteroaryl ketone derivatives of monic acid (2a) are reported. The best results were found for the 3-furyl and 2-methoxy thiazol-5-yl analogues.

  报道了一元酸（2a）的一系列芳基和杂芳基酮衍生物的合成，抗菌活性，鼠药代动力学和感染模型数据。对于3-呋喃基和2-甲氧基噻唑-5-基类似物，发现了最佳结果。
• Synthesis and antibacterial properties of β-diketone acrylate bioisosteres of pseudomonic acid A
  作者：Isobel Bennett、Nigel J.P. Broom、Robert Cassels、John S. Elder、Nicky D. Masson、Peter J. O'Hanlon

  DOI：10.1016/s0960-894x(99)00296-6

  日期：1999.7

  A series of beta-diketone acrylate bioisosteres 4 of pseudomonic acid A 1 have been synthesized and evaluated for their ability to inhibit bacterial isoleucyl-tRNA synthetase and act as antibacterial agents. A number of analogues have excellent antibacterial activity. Selected examples were shown to afford good blood levels and to be effective in a murine infection model. (C) 1999 Elsevier Science Ltd. All rights reserved.