(2R)-N-Benzoyl-2-(tert-butyl)-4-methylidene-1,3-oxazolidin-5-one | 147092-28-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R)-N-Benzoyl-2-(tert-butyl)-4-methylidene-1,3-oxazolidin-5-one
• 英文别名: (2S)-2-tert-butyl-3-benzoyl-4-methyleneoxazolidin-5-one；(2R)-3-benzoyl-2-t-butyl-4-methyleneoxazolidin-5-one；(2R)-N-benzoyl-2-t-butyl-4-methyleneoxazolidin-5-one；(2R)-3-benzoyl-2-tert-butyl-4-methylidene-1,3-oxazolidin-5-one
• CAS: 147092-28-2
• 化学式: C₁₅H₁₇NO₃
• 分子量: 259.305
• InChiKey: OXVRRDGBYLOQEQ-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(1-吡咯烷)环戊烯 、 (2R)-N-Benzoyl-2-(tert-butyl)-4-methylidene-1,3-oxazolidin-5-one 在 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 生成 (2S,4S)-3-benzoyl-2-tert-butyl-4-(2'-oxo-1'-cyclopentyl)methyloxazolidin 、 (2S,4R)-3-benzoyl-2-tert-butyl-4-(2'-oxo-1'-cyclopentyl)methyloxazolidin-5-one
  参考文献：
  名称：

  Asymmetric synthesis of proline derivatives from (2R) and (2S)-2-tert-butyl-3-benzoyl-4-methyleneoxazolidin-5-one

  摘要：

  The conjugate addition of enamines (2a,b) to the chiral oxazolidinones (1) or ent-(1) favours cis 2,4-substituted oxazolidinone adducts while trans 2,4-substituted oxazolidinone adducts are favoured from the addition reactions of enamine (2c). The diastereomeric adducts from the addition of (2a) to (1) are readily separated and can be converted to (5R, 2S) and (5S, 2R) 5-iso-propyl proline efficiently and in good overall yield. The extenstion of this protocol to the synthesis of perhydroindole carboxylic acid suffered from poor overall stereochemical control.

  DOI：

  10.1016/0040-4020(95)98711-p
• 作为产物：
  描述：

  (2R,4S)-3-苯甲酰基-2-(叔丁基)-4-甲基-1,3-恶唑烷-5-酮 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 sodium iodide 作用下， 生成 (2R)-N-Benzoyl-2-(tert-butyl)-4-methylidene-1,3-oxazolidin-5-one
  参考文献：
  名称：

  Beckwith, Athelstan L. J.; Pyne, Stephen G.; Dikic, Branko, Australian Journal of Chemistry, 1993, vol. 46, # 9, p. 1425 - 1430

  摘要：

  DOI：

文献信息

• Two free radical routes for the preparation of novel difluoromethylene-linked serine-O-glycopeptide analogues
  作者：Timothée F. Herpin、William B. Motherwell、Jean-Marc Weibel

  DOI：10.1039/a700928c

  日期：——

  The first examples of gem-difluoromethylene-linked analogues of serine-derived glycopeptides have been prepared in a highly stereoselective manner using two complementary free radical chain reactions.

  采用两种互补的自由基链反应，以高立体选择性的方式合成了首批氟代二甲撑连接的丝氨酸衍生的糖肽类似物。
• Pyne, Stephen G.; Dikic, Branko; Gordon, Peter A., Australian Journal of Chemistry, 1993, vol. 46, # 1, p. 73 - 93
  作者：Pyne, Stephen G.、Dikic, Branko、Gordon, Peter A.、Skelton, Brian W.、White, Allan H.

  DOI：——

  日期：——
• Beckwith Athelstan L. J., Pyne Stephen G., Dikic Branko, Chai Christina L+, Austral. J. Chem, 46 (1993) N 9, S 1425-1430
  作者：Beckwith Athelstan L. J., Pyne Stephen G., Dikic Branko, Chai Christina L+

  DOI：——

  日期：——
• Asymmetric synthesis of proline derivatives from (2R) and (2S)-2-tert-butyl-3-benzoyl-4-methyleneoxazolidin-5-one
  作者：Stephen G Pyne、Abdollah Javidan、Brian W Skelton、Allan H White

  DOI：10.1016/0040-4020(95)98711-p

  日期：1995.4

  The conjugate addition of enamines (2a,b) to the chiral oxazolidinones (1) or ent-(1) favours cis 2,4-substituted oxazolidinone adducts while trans 2,4-substituted oxazolidinone adducts are favoured from the addition reactions of enamine (2c). The diastereomeric adducts from the addition of (2a) to (1) are readily separated and can be converted to (5R, 2S) and (5S, 2R) 5-iso-propyl proline efficiently and in good overall yield. The extenstion of this protocol to the synthesis of perhydroindole carboxylic acid suffered from poor overall stereochemical control.
• Beckwith, Athelstan L. J.; Pyne, Stephen G.; Dikic, Branko, Australian Journal of Chemistry, 1993, vol. 46, # 9, p. 1425 - 1430
  作者：Beckwith, Athelstan L. J.、Pyne, Stephen G.、Dikic, Branko、Chai, Christina L. L.、Gordon, Peter A.、et al.

  DOI：——

  日期：——