4-[2-(3-oxo-propyl)-1,3-dithian-2-yl]-but-2-enal | 871469-07-7

• 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: 4-[2-(3-oxo-propyl)-1,3-dithian-2-yl]-but-2-enal
• 英文别名: (E)-4-[2-(3-oxopropyl)-1,3-dithian-2-yl]but-2-enal
• CAS: 871469-07-7
• 化学式: C₁₁H₁₆O₂S₂
• 分子量: 244.379
• InChiKey: LSABANUTMCOXTQ-OWOJBTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  4-[2-(3-oxo-propyl)-1,3-dithian-2-yl]-but-2-enal 、 (4R)-2,2-dimethyl-N-naphthalen-1-yl-1,3-thiazolidine-4-carboxamide;2,2,2-trifluoroacetic acid 以 丙酮 为溶剂， 反应 0.25h， 以100%的产率得到(4R)-3-[(1'S,4'aS,7'aS)-spiro[1,3-dithiane-2,6'-4a,5,7,7a-tetrahydro-1H-cyclopenta[c]pyran]-1'-yl]-2,2-dimethyl-N-naphthalen-1-yl-1,3-thiazolidine-4-carboxamide
  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：

  tert-butyl-(3-1,3-dithian-2-yl-propoxy)-dimethyl-silane 在 盐酸 、 正丁基锂 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 二甲基亚砜 、 丙酮 为溶剂， 反应 6.0h， 生成 4-[2-(3-oxo-propyl)-1,3-dithian-2-yl]-but-2-enal
  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.