(4S)-3-benzoyl-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-ethenyl-1,3-oxazolidin-2-one | 208935-22-2

• 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: (4S)-3-benzoyl-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-ethenyl-1,3-oxazolidin-2-one
• CAS: 208935-22-2
• 化学式: C₁₉H₂₇NO₄Si
• 分子量: 361.513
• InChiKey: OPIWOPSBFXQOTI-VYRBHSGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.22
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (4S)-3-benzoyl-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-ethenyl-1,3-oxazolidin-2-one 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 1,3-双(二苯基膦)丙烷 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 ((4S,5S)-2-Phenyl-5-vinyl-4,5-dihydro-oxazol-4-yl)-methanol
  参考文献：
  名称：

  Synthesis and evaluation of novel oxazoline MMP inhibitors

  摘要：

  MMP inhibitors with novel oxazoline zinc binding groups have been synthesized and evaluated. Selectivity for the inhibition of MMP-9 over MMP-1, MMP-2, and MMP-12 has been achieved in several cases. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.023
• 作为产物：
  描述：

  tert-butyl (S)-1-(tert-butyldimethylsilyloxy)-3-oxopropan-2-yl carbamate 在 sodium hydride 、 三乙胺 作用下， 生成 (4S)-3-benzoyl-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-ethenyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Synthesis and evaluation of novel oxazoline MMP inhibitors

  摘要：

  MMP inhibitors with novel oxazoline zinc binding groups have been synthesized and evaluated. Selectivity for the inhibition of MMP-9 over MMP-1, MMP-2, and MMP-12 has been achieved in several cases. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.023

文献信息

• Palladium-catalyzed formation and stereoselective isomerization of 5-vinyloxazolines. Application to the formal synthesis of (S,S)-4-amino-3-hydroxy-5-phenylpentanoic acid
  作者：Gregory R. Cook、P. Sathya Shanker

  DOI：10.1016/s0040-4039(98)00534-6

  日期：1998.5

  Vinyloxazolidinones have been found to undergo Pd(0)-catalyzed ionization followed by loss of carbon dioxide and subsequent cyclization to form vinyloxazolines. The reaction occurred under mild conditions, and enhancement of diastereomeric ratios with chiral substrates was obtained. 4-Benzyl-5-vinyloxazoline prepared by this method has been utilized in the stereoselective synthesis of (S,S)-4-amino-3-hydroxy-5-phenylpentanoic acid (AHPPA). (C) 1998 Elsevier Science Ltd. All rights reserved.
• Palladium-Mediated Dynamic Kinetic Resolution: Stereoselective Synthesis of Vicinal Diamines
  作者：Gregory R. Cook、P. Sathya Shanker、Ketheeswaran Pararajasingham

  DOI：10.1002/(sici)1521-3773(19990115)38:1/2<110::aid-anie110>3.0.co;2-l

  日期：1999.1.15