(2S,4S)-2-Pent-4-enoyl-4-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester | 360776-11-0

• 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)-2-Pent-4-enoyl-4-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2S,4S)-2-pent-4-enoyl-4-phenyl-1,3-oxazolidine-3-carboxylate
• CAS: 360776-11-0
• 化学式: C₁₉H₂₅NO₄
• 分子量: 331.412
• InChiKey: YZXKOHUPBDLNQQ-WBVHZDCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,4S)-2-Pent-4-enoyl-4-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester 在 palladium on activated charcoal 氢氧化钾 、 sodium tetrahydroborate 、 Grubbs catalyst first generation 、 mercury(II) diacetate 、 氢气 、 四氯化钛 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 生成 (1S,2S,6S)-2-Hydroxy-9-aza-bicyclo[4.2.1]nonane-9-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Ring-closing metathesis of diolefinic oxazolidinones: a new access to tropanes and aminocyclitols

  摘要：

  Ring-closing metathesis of diolefinic oxazolidinones prepared through N-Boc-2-acyl or alpha,beta -epoxy oxazolidine methodology give stereodefined bicyclic oxazolidinones. The 5,6-membered bicyclic oxazolidinones are then converted into new aminocyclitols by diastereoselective dihydroxylation whereas their 5,7-membered bicyclic homologues are transformed into tropanic alkaloids through an aminocyclization step. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00830-9
• 作为产物：
  描述：

  3-Butenylmagnesium bromide 、 (2S,4S)-2-(Methoxy-methyl-carbamoyl)-4-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester 生成 (2S,4S)-2-Pent-4-enoyl-4-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Ring-closing metathesis of diolefinic oxazolidinones: a new access to tropanes and aminocyclitols

  摘要：

  Ring-closing metathesis of diolefinic oxazolidinones prepared through N-Boc-2-acyl or alpha,beta -epoxy oxazolidine methodology give stereodefined bicyclic oxazolidinones. The 5,6-membered bicyclic oxazolidinones are then converted into new aminocyclitols by diastereoselective dihydroxylation whereas their 5,7-membered bicyclic homologues are transformed into tropanic alkaloids through an aminocyclization step. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00830-9

文献信息

• Ring-closing metathesis of diolefinic oxazolidinones: a new access to tropanes and aminocyclitols
  作者：Claude Agami、François Couty、Nicolas Rabasso

  DOI：10.1016/s0040-4039(01)00830-9

  日期：2001.7

  Ring-closing metathesis of diolefinic oxazolidinones prepared through N-Boc-2-acyl or alpha,beta -epoxy oxazolidine methodology give stereodefined bicyclic oxazolidinones. The 5,6-membered bicyclic oxazolidinones are then converted into new aminocyclitols by diastereoselective dihydroxylation whereas their 5,7-membered bicyclic homologues are transformed into tropanic alkaloids through an aminocyclization step. (C) 2001 Elsevier Science Ltd. All rights reserved.