2-(1,3-Dithian-2-yl(hydroxy)methyl)-1,3-dithiane-2-carbaldehyde | 907177-36-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: 2-(1,3-Dithian-2-yl(hydroxy)methyl)-1,3-dithiane-2-carbaldehyde
• 英文别名: 2-[1,3-dithian-2-yl(hydroxy)methyl]-1,3-dithiane-2-carbaldehyde
• CAS: 907177-36-0
• 化学式: C₁₀H₁₆O₂S₄
• 分子量: 296.5
• InChiKey: WXWPFALNLAQILY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  139
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(1,3-Dithian-2-yl(hydroxy)methyl)-1,3-dithiane-2-carbaldehyde 在 正丁基锂 作用下， -78.0~120.0 ℃ 、133.32 Pa 条件下， 反应 1.5h， 生成 (4S)-3-<1-oxo-3-(1,3-dithian-2-ylidene)propyl>-4-(1-methylethyl)-2-oxazolidinone
  参考文献：
  名称：

  Enantioselective preparation of .beta.-alkyl-.gamma.-butyrolactones from functionalized ketene dithioacetals

  摘要：

  An efficient and general enantioselective synthesis of beta-alkyl-gamma-butyrolactones has been developed. The key step of this procedure is an oxazolidinone-directed alkylation of a lithiated ketene dithioacetal that proceeds with excellent regiochemical control and high diastereofacial selectivity. Reductive removal of the chiral auxiliary followed by acid-induced cyclization of the resultant hydroxy ketene dithioacetal gives the enantiomerically pure beta-alkyl-gamma-butyrolactone.

  DOI：

  10.1021/jo00062a013
• 作为产物：
  描述：

  1,3-二噻烷 、 N,N-二甲基甲酰胺 生成 2-(1,3-Dithian-2-yl(hydroxy)methyl)-1,3-dithiane-2-carbaldehyde
  参考文献：
  名称：

  Enantioselective preparation of .beta.-alkyl-.gamma.-butyrolactones from functionalized ketene dithioacetals

  摘要：

  An efficient and general enantioselective synthesis of beta-alkyl-gamma-butyrolactones has been developed. The key step of this procedure is an oxazolidinone-directed alkylation of a lithiated ketene dithioacetal that proceeds with excellent regiochemical control and high diastereofacial selectivity. Reductive removal of the chiral auxiliary followed by acid-induced cyclization of the resultant hydroxy ketene dithioacetal gives the enantiomerically pure beta-alkyl-gamma-butyrolactone.

  DOI：

  10.1021/jo00062a013

文献信息

• Koch Stacie S. Canan, Chamberlin A. Richard, J. Org. Chem., 58 (1993) N 10, S 2725-2737
  作者：Koch Stacie S. Canan, Chamberlin A. Richard

  DOI：——

  日期：——
• Enantioselective preparation of .beta.-alkyl-.gamma.-butyrolactones from functionalized ketene dithioacetals
  作者：Stacie S. Canan Koch、A. Richard Chamberlin

  DOI：10.1021/jo00062a013

  日期：1993.5

  An efficient and general enantioselective synthesis of beta-alkyl-gamma-butyrolactones has been developed. The key step of this procedure is an oxazolidinone-directed alkylation of a lithiated ketene dithioacetal that proceeds with excellent regiochemical control and high diastereofacial selectivity. Reductive removal of the chiral auxiliary followed by acid-induced cyclization of the resultant hydroxy ketene dithioacetal gives the enantiomerically pure beta-alkyl-gamma-butyrolactone.