(R)-2-Methyl-5-oxo-tetrahydrofuran-2-carbonsaeure-methylester | 21461-87-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (R)-2-Methyl-5-oxo-tetrahydrofuran-2-carbonsaeure-methylester
• 英文别名: methyl (R)-tetrahydro-5-oxo-2-methyl-2-furancarboxylate；(R)-2-methyl-5-oxo-tetrahydro-furan-2-carboxylic acid methyl ester；methyl (2R)-2-methyl-5-oxooxolane-2-carboxylate
• CAS: 21461-87-0
• 化学式: C₇H₁₀O₄
• 分子量: 158.154
• InChiKey: TUTGZLNPAYBACN-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-2-Methyl-5-oxo-tetrahydrofuran-2-carbonsaeure-methylester 在 lithium aluminium tetrahydride 作用下， 生成 (R)-(+)-2-Methyl-1,2,5-pentantriol
  参考文献：
  名称：

  Cervinka,O.; Hub,L., Collection of Czechoslovak Chemical Communications, 1968, vol. 33, # 9, p. 2927 - 2932

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl (Z)-3-[(R)-5H-5-methyl-4-oxo-2-phenyloxazol-5-yl]propenoate 在 palladium 10% on activated carbon 、 lithium methanolate 、 氢气 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 85.4h， 生成 (R)-2-Methyl-5-oxo-tetrahydrofuran-2-carbonsaeure-methylester
  参考文献：
  名称：

  HighlyZ-Selective Asymmetric 1,4-Addition Reaction of 5H-Oxazol-4-ones with Alkynyl Carbonyl Compounds Catalyzed by Chiral Guanidines

  摘要：

  An asymmetric I,4-addition reaction of 5H-oxazol-4-ones with alkynyl carbonyl compounds was developed, and, for the first time, high enantiomeric and geometric control was achieved to afford the thermodynamically unstable Z-isomer predominantly using chiral guanidine catalysts bearing a hydroxy group at the appropriate position. The method provides synthetically useful gamma-butenolide ester bearing a chiral quaternary stereogenic center.

  DOI：

  10.1021/ja200283n

文献信息

• Asymmetric synthesis of furanones
  作者：Didier Desmaele、Jean d'Angelo、Claudette Bois

  DOI：10.1016/s0957-4166(00)80438-3

  日期：1990.1
• Cervinka,O.; Hub,L., Collection of Czechoslovak Chemical Communications, 1968, vol. 33, # 9, p. 2927 - 2932
  作者：Cervinka,O.、Hub,L.

  DOI：——

  日期：——
• Highly<i>Z</i>-Selective Asymmetric 1,4-Addition Reaction of 5<i>H</i>-Oxazol-4-ones with Alkynyl Carbonyl Compounds Catalyzed by Chiral Guanidines
  作者：Tomonori Misaki、Kei Kawano、Takashi Sugimura

  DOI：10.1021/ja200283n

  日期：2011.4.20

  An asymmetric I,4-addition reaction of 5H-oxazol-4-ones with alkynyl carbonyl compounds was developed, and, for the first time, high enantiomeric and geometric control was achieved to afford the thermodynamically unstable Z-isomer predominantly using chiral guanidine catalysts bearing a hydroxy group at the appropriate position. The method provides synthetically useful gamma-butenolide ester bearing a chiral quaternary stereogenic center.