(S)-2-benzyl-5-oxo-tetrahydrofuran | 1024613-10-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (S)-2-benzyl-5-oxo-tetrahydrofuran
• 英文别名: (2S)-2-benzyl-5-oxooxolane-2-carboxylic acid
• CAS: 1024613-10-2
• 化学式: C₁₂H₁₂O₄
• 分子量: 220.225
• InChiKey: BTPPRYXIACOMCP-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-benzyl-5-oxo-tetrahydrofuran 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以83%的产率得到(S)-5-benzyl-5-(hydroxymethyl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Asymmetric synthesis of 4′-C-benzyl-2′,3′-dideoxynucleoside analogues from 3-benzyl-2-hydroxy-2-cyclopenten-1-one

  摘要：

  Both enantiomers of the key intermediate, 2-benzyl-5-oxo-tetrahydro-furan-2-carboxylic acid were obtained by asymmetric oxidation of 3 -benzyl-2-hyd roxy-2-cyclopen ten- 1 -one with all ee >= 96%, using the tartaric ester/Ti(OiPr)(4)/t-BuOOH complex, and transformed to the corresponding 4'-substituted nucleoside analogues with up to 61% overall yield. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.01.028
• 作为产物：
  描述：

  3-苄基-2-羟基环戊烯-2-酮 在 titanium(IV) isopropylate 、 L-(+)-酒石酸二乙酯 、 叔丁基过氧化氢 作用下， 以 二氯甲烷 、 癸烷 为溶剂， 反应 48.5h， 以83%的产率得到(S)-2-benzyl-5-oxo-tetrahydrofuran
  参考文献：
  名称：

  Asymmetric Synthesis of Tertiary 2-Substituted 5-Oxotetrahydrofuran-2-carboxylic Acids

  摘要：

  3-Substituted 1,2-cyclopentanediones 1 were transformed to 2-substituted 5-oxotetrahydrofuran-2-carboxylic acids 2 using a catalytic process with 0.2-0.3 equivalent of Ti(OiPr)(4)/tartaric ester/tBuO0H complex in up to 72% isolated yield and up to 94% ee. Different functional groups in the 3-alkyl substituent of 1 like, hydroxy, ether, Boc-amino and ester groups are tolerated. Boc-aminomethyl substitu.ents lead to beta-amino acid analogues and Boc-aminoethyl substituent to gamma-amino acid analogues as well as spiro-lactonelactams. A direct, two-step procedure for homocitric acid synthesis is described.

  DOI：

  10.3987/com-13-s(s)28

文献信息

• Asymmetric synthesis of 4′-C-benzyl-2′,3′-dideoxynucleoside analogues from 3-benzyl-2-hydroxy-2-cyclopenten-1-one
  作者：Artur Jõgi、Marit Ilves、Anne Paju、Tõnis Pehk、Tiiu Kailas、Aleksander-Mati Müürisepp、Margus Lopp

  DOI：10.1016/j.tetasy.2008.01.028

  日期：2008.3

  Both enantiomers of the key intermediate, 2-benzyl-5-oxo-tetrahydro-furan-2-carboxylic acid were obtained by asymmetric oxidation of 3 -benzyl-2-hyd roxy-2-cyclopen ten- 1 -one with all ee >= 96%, using the tartaric ester/Ti(OiPr)(4)/t-BuOOH complex, and transformed to the corresponding 4'-substituted nucleoside analogues with up to 61% overall yield. (C) 2008 Elsevier Ltd. All rights reserved.
• Asymmetric Synthesis of Tertiary 2-Substituted 5-Oxotetrahydrofuran-2-carboxylic Acids
  作者：Margus Lopp、Anne Paju、Karolin Oja、Katharina Matkevitš、Priit Lumi、Ivar Järving、Tõnis Pehk

  DOI：10.3987/com-13-s(s)28

  日期：——

  3-Substituted 1,2-cyclopentanediones 1 were transformed to 2-substituted 5-oxotetrahydrofuran-2-carboxylic acids 2 using a catalytic process with 0.2-0.3 equivalent of Ti(OiPr)(4)/tartaric ester/tBuO0H complex in up to 72% isolated yield and up to 94% ee. Different functional groups in the 3-alkyl substituent of 1 like, hydroxy, ether, Boc-amino and ester groups are tolerated. Boc-aminomethyl substitu.ents lead to beta-amino acid analogues and Boc-aminoethyl substituent to gamma-amino acid analogues as well as spiro-lactonelactams. A direct, two-step procedure for homocitric acid synthesis is described.