(2S,4S,5R)-1-<4-methyl-5-phenyl-3-(toluene-4'-sulfonyl)-oxazolidin-2-yl>-ethanone | 143738-95-8

• 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: (2S,4S,5R)-1-<4-methyl-5-phenyl-3-(toluene-4'-sulfonyl)-oxazolidin-2-yl>-ethanone
• 英文别名: 1-[(2S,4S,5R)-4-methyl-3-(4-methylphenyl)sulfonyl-5-phenyl-1,3-oxazolidin-2-yl]ethanone
• CAS: 143738-95-8
• 化学式: C₁₉H₂₁NO₄S
• 分子量: 359.446
• InChiKey: LGNPUNUSNIAFQQ-JVPBZIDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,4S,5R)-1-<4-methyl-5-phenyl-3-(toluene-4'-sulfonyl)-oxazolidin-2-yl>-ethanone 在 L-Selectride 、 magnesium bromide 作用下， 生成 (1R,2'S,4'S,5'R)-1-<4'-methyl-5'-phenyl-3'-(toluene-4''-sulfonyl)-oxazolidin-2'-yl>-ethanol
  参考文献：
  名称：

  Manzoni, Leonardo; Poli, Giovanni; Scolastico, Carlo, Phosphorus, Sulfur and Silicon and the Related Elements, 1993, vol. 74, # 1-4, p. 381 - 382

  摘要：

  DOI：
• 作为产物：
  描述：

  (2S,4S,5R)-2-isopropenyl-4-methyl-5-phenyl-3-(toluene-4'-sulfonyl)-oxazolidine 在 sodium periodate 、 osmium (III) chloride 、 十二/十四烷基二甲基氧化胺 、 水 作用下， 以 1,4-二氧六环 、 水 、 丙酮 为溶剂， 反应 2.0h， 生成 (2S,4S,5R)-1-<4-methyl-5-phenyl-3-(toluene-4'-sulfonyl)-oxazolidin-2-yl>-ethanone
  参考文献：
  名称：

  Diastereoselective addition of metal-coordinated and ‘naked’ tri-sec-butylborohydrides to a norephedrine-derived 2-acetyloxazolidine

  摘要：

  在螯合或非配位条件下，将三仲丁基硼氢化物加成到 2-乙酰基-1,3-恶唑烷 1 上，可以分别高选择性地定向到 Si 或 Re-羰基面。

  DOI：

  10.1039/c39920001027

文献信息

• Diastereoselective addition of metal-coordinated and “naked” nucleophilic reagents to norephedrine derived 2-acyl-N-tosyl-oxazolidines
  作者：Giovanni Poli、Elisa Maccagni、Leonardo Manzoni、Tullio Pilati、Carlo Scolastico

  DOI：10.1016/s0040-4020(96)01087-3

  日期：1997.2

  The addition of tri-s-butyl borohydrides to the 2-acetyl-1,3-oxazolidine 1 could be directed with high selectivity to either the Si or the Re pi-carbonyl face under chelating or non-coordinating conditions respectively. Addition of hydrides to the corresponding phenyl ketone 2 was highly Si selective only in the former conditions. Grignard reagents and organolithiums add to the methyl ketone 1 with remarkable Si and Re pi-face selectivity respectively. With phenyl ketone 2 only organomagnesium reagents follow the above trend. This data are in accord with a Felkin-type or a stereochemically opposite chelaled mode of addition of these nucleophiles in the absence or in the presence of chelating metal counterions respectively. (C) 1997, Published by Elsevier Science Ltd.
• Diastereoselective addition of metal-coordinated and ‘naked’ tri-sec-butylborohydrides to a norephedrine-derived 2-acetyloxazolidine
  作者：Leonardo Manzoni、Tullio Pilati、Giovanni Poli、Carlo Scolastico

  DOI：10.1039/c39920001027

  日期：——

  The addition of tri-sec-butylborohydrides to the 2-acetyl-1,3-oxazolidine 1 can be directed with high selectivity to either the Si or the Reπ-carbonyl face under chelating or non-coordinating conditions, respectively.

  在螯合或非配位条件下，将三仲丁基硼氢化物加成到 2-乙酰基-1,3-恶唑烷 1 上，可以分别高选择性地定向到 Si 或 Re-羰基面。
• Manzoni, Leonardo; Poli, Giovanni; Scolastico, Carlo, Phosphorus, Sulfur and Silicon and the Related Elements, 1993, vol. 74, # 1-4, p. 381 - 382
  作者：Manzoni, Leonardo、Poli, Giovanni、Scolastico, Carlo

  DOI：——

  日期：——