3-[2-(4-oxo-pent-2-enyl)-1,3-dithian-2-yl]-propionaldehyde | 871469-01-1

• 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: 3-[2-(4-oxo-pent-2-enyl)-1,3-dithian-2-yl]-propionaldehyde
• 英文别名: 3-[2-[(E)-4-oxopent-2-enyl]-1,3-dithian-2-yl]propanal
• CAS: 871469-01-1
• 化学式: C₁₂H₁₈O₂S₂
• 分子量: 258.406
• InChiKey: FIUALIAOQNRGKD-GORDUTHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[2-(4-oxo-pent-2-enyl)-1,3-dithian-2-yl]-propionaldehyde 在 (4R)-N-(naphthyl)-2,2-Me₂-thiazolidine-4-carboxamide trifluoroacetate 作用下， 以 丙酮 为溶剂， 反应 2.5h， 以93%的产率得到(3S,4S)-3-(2-oxo-propyl)-6,10-dithia-spiro[4.5]decane-2-carbaldehyde
  参考文献：
  名称：

  Cysteine-Derived Organocatalyst in a Highly Enantioselective Intramolecular Michael Reaction

  摘要：

  Asymmetric intramolecular Michael reaction catalyzed by an organocatalyst derived from cysteine has been developed for the synthesis of chiral bicyclo[4.3.0]nonene and cis-disubstituted cyclopentane skeletons with a creation of three or two contiguous chiral centers in good yield with high diastereo- and excellent enantioselectivities.

  DOI：

  10.1021/ja055740s
• 作为产物：
  描述：

  2-(2,2-dimethoxyethyl)1,3-dithiane 在 盐酸 、 六甲基磷酰三胺 、 正丁基锂 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 、 丙酮 为溶剂， 反应 5.0h， 生成 3-[2-(4-oxo-pent-2-enyl)-1,3-dithian-2-yl]-propionaldehyde
  参考文献：
  名称：

  Cysteine-Derived Organocatalyst in a Highly Enantioselective Intramolecular Michael Reaction

  摘要：

  Asymmetric intramolecular Michael reaction catalyzed by an organocatalyst derived from cysteine has been developed for the synthesis of chiral bicyclo[4.3.0]nonene and cis-disubstituted cyclopentane skeletons with a creation of three or two contiguous chiral centers in good yield with high diastereo- and excellent enantioselectivities.

  DOI：

  10.1021/ja055740s

文献信息

• Cysteine-Derived Organocatalyst in a Highly Enantioselective Intramolecular Michael Reaction
  作者：Yujiro Hayashi、Hiroaki Gotoh、Tomohiro Tamura、Hirofumi Yamaguchi、Ryouhei Masui、Mitsuru Shoji

  DOI：10.1021/ja055740s

  日期：2005.11.23

  Asymmetric intramolecular Michael reaction catalyzed by an organocatalyst derived from cysteine has been developed for the synthesis of chiral bicyclo[4.3.0]nonene and cis-disubstituted cyclopentane skeletons with a creation of three or two contiguous chiral centers in good yield with high diastereo- and excellent enantioselectivities.