Methyl (2R,3R,4R)-<4-methyl-5-oxo-4-(phenylthio)-2-propyltetrahydrofuran-3-yl>acetate | 134829-46-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: Methyl (2R,3R,4R)-<4-methyl-5-oxo-4-(phenylthio)-2-propyltetrahydrofuran-3-yl>acetate
• 英文别名: methyl 2-[(2R,3R,4R)-4-methyl-5-oxo-4-phenylsulfanyl-2-propyloxolan-3-yl]acetate
• CAS: 134829-46-2
• 化学式: C₁₇H₂₂O₄S
• 分子量: 322.425
• InChiKey: NCJAJRRRBIPPOW-CKEIUWERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  77.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl (2R,3R,4R)-<4-methyl-5-oxo-4-(phenylthio)-2-propyltetrahydrofuran-3-yl>acetate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以96%的产率得到Methyl (2R,3R,4R)-<4-(benzenesulfinyl)-4-methyl-5-oxo-2-propyltetrahydrofuran-3-yl>acetate
  参考文献：
  名称：

  Stereoselective Synthesis of Highly Substituted .gamma.-Lactones and Butenolides by Intramolecular Michael Addition of Enantiomerically Enriched .gamma.-[(Phenylthio)acyl]oxy .alpha.,.beta.-Unsaturated Esters

  摘要：

  The synthesis of polysubstituted gamma-lactones by the base-induced cyclization of enantiomerically enriched gamma-((phenylthio)acyl)oxy alpha,beta-unsaturated esters obtained from 2,3-epoxy alcohols is described. The procedure is highly stereoselective and compatible with a wide range of functionalities (ester, tetrahydropyranyl ether, silyl ether, etc.). Varying degrees of substitution, including quaternary centers, in the final gamma-lactone were synthesized with excellent stereoselectivity. Useful functional interconversions were successfully demonstrated, in particular those resulting in butenolides. By the use of AM1 it was concluded that the intramolecular Michael reaction can be described as a kinetically controlled reaction in which the relative stability of the transition states for all possible final configurations led to geometries in agreement with the experimental results.

  DOI：

  10.1021/jo00095a022
• 作为产物：
  描述：

  (2S,3S)-(-)-3-丙基环氧乙烷甲醇 在 titanium(IV) isopropylate 、 sodium periodate 、 sodium hydride 、 四丁基高碘酸铵 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 paraffin 为溶剂， 反应 7.83h， 生成 Methyl (2R,3R,4R)-<4-methyl-5-oxo-4-(phenylthio)-2-propyltetrahydrofuran-3-yl>acetate
  参考文献：
  名称：

  Stereoselective Synthesis of Highly Substituted .gamma.-Lactones and Butenolides by Intramolecular Michael Addition of Enantiomerically Enriched .gamma.-[(Phenylthio)acyl]oxy .alpha.,.beta.-Unsaturated Esters

  摘要：

  The synthesis of polysubstituted gamma-lactones by the base-induced cyclization of enantiomerically enriched gamma-((phenylthio)acyl)oxy alpha,beta-unsaturated esters obtained from 2,3-epoxy alcohols is described. The procedure is highly stereoselective and compatible with a wide range of functionalities (ester, tetrahydropyranyl ether, silyl ether, etc.). Varying degrees of substitution, including quaternary centers, in the final gamma-lactone were synthesized with excellent stereoselectivity. Useful functional interconversions were successfully demonstrated, in particular those resulting in butenolides. By the use of AM1 it was concluded that the intramolecular Michael reaction can be described as a kinetically controlled reaction in which the relative stability of the transition states for all possible final configurations led to geometries in agreement with the experimental results.

  DOI：

  10.1021/jo00095a022

文献信息

• An approach to the stereocontrolled synthesis of polysubstituted chiral butenolides and γ-lactones
  作者：Carmen Ma Rodríguez、Victor S. Martín

  DOI：10.1016/s0040-4039(00)71265-2

  日期：1991.5

  The enantioselective synthesis of polysubstituted butenolides and gamma-lactones by an intramolecular Michael addition of chiral thiophenylacetates of gamma-hydroxy-alpha,beta-unsaturated esters is described.
• Rodriguez Carmen M., Martin Tomas, Ramirez Miguel A., Martin iVictor S., J. Org. Chem, 59 (1994) N 16, S 4461-4472
  作者：Rodriguez Carmen M., Martin Tomas, Ramirez Miguel A., Martin iVictor S.

  DOI：——

  日期：——
• Stereoselective Synthesis of Highly Substituted .gamma.-Lactones and Butenolides by Intramolecular Michael Addition of Enantiomerically Enriched .gamma.-[(Phenylthio)acyl]oxy .alpha.,.beta.-Unsaturated Esters
  作者：Carmen M. Rodriguez、Tomas Martin、Miguel A. Ramirez、Victor S. Martin

  DOI：10.1021/jo00095a022

  日期：1994.8

  The synthesis of polysubstituted gamma-lactones by the base-induced cyclization of enantiomerically enriched gamma-((phenylthio)acyl)oxy alpha,beta-unsaturated esters obtained from 2,3-epoxy alcohols is described. The procedure is highly stereoselective and compatible with a wide range of functionalities (ester, tetrahydropyranyl ether, silyl ether, etc.). Varying degrees of substitution, including quaternary centers, in the final gamma-lactone were synthesized with excellent stereoselectivity. Useful functional interconversions were successfully demonstrated, in particular those resulting in butenolides. By the use of AM1 it was concluded that the intramolecular Michael reaction can be described as a kinetically controlled reaction in which the relative stability of the transition states for all possible final configurations led to geometries in agreement with the experimental results.