(4S,5S)-3-Acryloyl-4-allyl-5-ethyl-oxazolidin-2-one | 287184-98-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S,5S)-3-Acryloyl-4-allyl-5-ethyl-oxazolidin-2-one
• 英文别名: (4S,5S)-3-Acryloyl-4-allyl-5-ethyloxazolidin-2-one；(4S,5S)-5-ethyl-3-prop-2-enoyl-4-prop-2-enyl-1,3-oxazolidin-2-one
• CAS: 287184-98-9
• 化学式: C₁₁H₁₅NO₃
• 分子量: 209.245
• InChiKey: UGCHLUWWWVTPMC-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  (4S,5S)-3-Acryloyl-4-allyl-5-ethyl-oxazolidin-2-one 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以36%的产率得到(1S,8aS)-1-Ethyl-8,8a-dihydro-1H-oxazolo[3,4-a]pyridine-3,5-dione
  参考文献：
  名称：

  Synthesis of (−)-β conhydrine and analogues using N-Boc-2-acyl oxazolidine methodology and ring closing metathesis

  摘要：

  Two key-steps involving: (i) a stereoselective reduction of an N-Boc-2-acyl oxazolidine; and (ii) an RCM performed on enantiopure trans-3,4,5-trisubstituted oxazolidin-2-ones account for the synthesis of unsaturated bicyclic oxazolidin-2-ones with various sizes of ring. One of these bicyclic compounds was transformed into (-)-beta-conhydrin. An unsaturated and a dihydroxylated analogue of this alcaloid were also prepared from the same starting material. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00580-3
• 作为产物：
  描述：

  (3S,6S,7S)-6-ethyl-3-phenyltetrahydro-1,5-dioxa-3a-aza-pentalen-4-one 在 乙基溴化镁 、 氨 、 sodium 、 四氯化钛 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 生成 (4S,5S)-3-Acryloyl-4-allyl-5-ethyl-oxazolidin-2-one
  参考文献：
  名称：

  Synthesis of (−)-β conhydrine and analogues using N-Boc-2-acyl oxazolidine methodology and ring closing metathesis

  摘要：

  Two key-steps involving: (i) a stereoselective reduction of an N-Boc-2-acyl oxazolidine; and (ii) an RCM performed on enantiopure trans-3,4,5-trisubstituted oxazolidin-2-ones account for the synthesis of unsaturated bicyclic oxazolidin-2-ones with various sizes of ring. One of these bicyclic compounds was transformed into (-)-beta-conhydrin. An unsaturated and a dihydroxylated analogue of this alcaloid were also prepared from the same starting material. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00580-3

文献信息

• Synthesis of (−)-β conhydrine and analogues using N-Boc-2-acyl oxazolidine methodology and ring closing metathesis
  作者：Claude Agami、François Couty、Nicolas Rabasso

  DOI：10.1016/s0040-4039(00)00580-3

  日期：2000.5

  Two key-steps involving: (i) a stereoselective reduction of an N-Boc-2-acyl oxazolidine; and (ii) an RCM performed on enantiopure trans-3,4,5-trisubstituted oxazolidin-2-ones account for the synthesis of unsaturated bicyclic oxazolidin-2-ones with various sizes of ring. One of these bicyclic compounds was transformed into (-)-beta-conhydrin. An unsaturated and a dihydroxylated analogue of this alcaloid were also prepared from the same starting material. (C) 2000 Elsevier Science Ltd. All rights reserved.