2-(5H)-furanon-3-yl methanesulfonate | 78646-86-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 2-(5H)-furanon-3-yl methanesulfonate
• 英文别名: (5-oxo-2H-furan-4-yl) methanesulfonate
• CAS: 78646-86-3
• 化学式: C₅H₆O₅S
• 分子量: 178.166
• InChiKey: HTFNPLQMZSQMCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  苄胺 、 2-(5H)-furanon-3-yl methanesulfonate 在 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 7.0h， 以42%的产率得到(2S,3S)-1-Benzyl-3-hydroxymethyl-aziridine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of aziridine-2-carboxylates via conjugate addition of an amine to 2-(5H)-furanon-3-yl methanesulfonate: application to the preparation of α-amino-β-hydroxy-γ-butyrolactone

  摘要：

  Conjugate addition of benzylamine to 2-(5H)-furanon-3-yl methanesulfonate in methanol afforded a 7:1 mixture of the trans and cis methyl N-benzyl-2-hydroxymethylaziridine-2-carboxylates 7 and 8, respectively. Treatment of 7 with benzyl alcohol in the presence of BF3. OEt2 then furnished, after hydrogenolysis, rac-cis alpha-amino-beta-hydroxy-gamma-butyrolactone (1). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00335-x
• 作为产物：
  描述：

  甲基磺酰氯 、 (3R,4R)-(-)-D-赤酮酸内酯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以78%的产率得到2-(5H)-furanon-3-yl methanesulfonate
  参考文献：
  名称：

  Synthesis of aziridine-2-carboxylates via conjugate addition of an amine to 2-(5H)-furanon-3-yl methanesulfonate: application to the preparation of α-amino-β-hydroxy-γ-butyrolactone

  摘要：

  Conjugate addition of benzylamine to 2-(5H)-furanon-3-yl methanesulfonate in methanol afforded a 7:1 mixture of the trans and cis methyl N-benzyl-2-hydroxymethylaziridine-2-carboxylates 7 and 8, respectively. Treatment of 7 with benzyl alcohol in the presence of BF3. OEt2 then furnished, after hydrogenolysis, rac-cis alpha-amino-beta-hydroxy-gamma-butyrolactone (1). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00335-x

文献信息

• A new straightforward synthesis of 2,3-aziridino-γ-lactones
  作者：Carole de Saint-Fuscien、Aurélie Tarrade、Philippe Dauban、Robert H Dodd

  DOI：10.1016/s0040-4039(00)01071-6

  日期：2000.8

  A concise synthesis of 2,3-aziridino-gamma-lactones starting from commercially available alpha,beta-dihydroxy-gamma-lactones is described. The strategy involves a Michael-type addition of benzylamine onto a key 2-(5H)-furanon-3-yl trifluoromethanesulfonate, followed by in situ cyclization to the aziridine without lactone-ring-opening. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis of aziridine-2-carboxylates via conjugate addition of an amine to 2-(5H)-furanon-3-yl methanesulfonate: application to the preparation of α-amino-β-hydroxy-γ-butyrolactone
  作者：Carole de Saint-Fuscien、Robert H Dodd

  DOI：10.1016/s0040-4039(00)00335-x

  日期：2000.4

  Conjugate addition of benzylamine to 2-(5H)-furanon-3-yl methanesulfonate in methanol afforded a 7:1 mixture of the trans and cis methyl N-benzyl-2-hydroxymethylaziridine-2-carboxylates 7 and 8, respectively. Treatment of 7 with benzyl alcohol in the presence of BF3. OEt2 then furnished, after hydrogenolysis, rac-cis alpha-amino-beta-hydroxy-gamma-butyrolactone (1). (C) 2000 Elsevier Science Ltd. All rights reserved.