3-((1R)-1-hydroxyethyl)-2(5H)-furanone | 144128-25-6

• 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: 3-((1R)-1-hydroxyethyl)-2(5H)-furanone
• 英文别名: (R)-3-(1-hydroxyethyl)furan-2(5H)-one；4-[(1R)-1-hydroxyethyl]-2H-furan-5-one
• CAS: 144128-25-6
• 化学式: C₆H₈O₃
• 分子量: 128.128
• InChiKey: KOYIHFDILLEMPG-SCSAIBSYSA-N

物化性质

• 沸点：
  328.0±17.0 °C(Predicted)
• 密度：
  1.273±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-((1R)-1-hydroxyethyl)-2(5H)-furanone 在 palladium on activated charcoal mercury(II) diacetate 、 氢气 、 potassium carbonate 、 三乙胺 作用下， 以 乙醇 为溶剂， 25.0~140.0 ℃ 、101.33 kPa 条件下， 反应 26.0h， 生成 毛果芸香碱
  参考文献：
  名称：

  A synthesis of pilocarpine

  摘要：

  Pilocarpine (1) was synthesized in seven steps starting from 2-acetylbutyrolactone. Chirality was introduced by asymmetric reduction of enone 4 and transferred via a Claisen rearrangement. A mild procedure for the preparation of 1,5-disubstituted imidazoles in the last synthetic operation led to pilocarpine unaccompanied by isopilocarpine.

  DOI：

  10.1021/jo00053a016
• 作为产物：
  描述：

  (1S,2R,6S,7R)-2-acetyl-4-oxatricyclo[5.2.1.02,6]dec-8-en-3-one 在 二乙醇胺 、 (+)-二异松蒎基氯硼烷 作用下， -30.0~425.0 ℃ 、1.33 Pa 条件下， 反应 2.0h， 生成 3-((1R)-1-hydroxyethyl)-2(5H)-furanone
  参考文献：
  名称：

  A synthesis of pilocarpine

  摘要：

  Pilocarpine (1) was synthesized in seven steps starting from 2-acetylbutyrolactone. Chirality was introduced by asymmetric reduction of enone 4 and transferred via a Claisen rearrangement. A mild procedure for the preparation of 1,5-disubstituted imidazoles in the last synthetic operation led to pilocarpine unaccompanied by isopilocarpine.

  DOI：

  10.1021/jo00053a016

文献信息

• General switch in regioselectivity in the Mukaiyama aldol reaction of silyloxyfuran with aldehydes in aqueous solvents
  作者：Marta Woyciechowska、Gwenael Forcher、Szymon Buda、Jacek Mlynarski

  DOI：10.1039/c2cc36656h

  日期：——

  An unexpected yet disciplined course of catalytic Mukaiyama-aldol reaction instead of the expected vinylogous Mukaiyama-aldol reaction has been observed for the reaction of silyloxyfuran with various aldehydes under Lewis acid catalytic control in water-containing solvents.

  第 V 组金属化合物与三氧化硫的反应
• A synthesis of pilocarpine
  作者：David A. Horne、Burkhard Fugmann、Kenichi Yakushijin、George Buchi

  DOI：10.1021/jo00053a016

  日期：1993.1

  Pilocarpine (1) was synthesized in seven steps starting from 2-acetylbutyrolactone. Chirality was introduced by asymmetric reduction of enone 4 and transferred via a Claisen rearrangement. A mild procedure for the preparation of 1,5-disubstituted imidazoles in the last synthetic operation led to pilocarpine unaccompanied by isopilocarpine.