3-Oxo-3-(2-sulfanylphenyl)propanal

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-Oxo-3-(2-sulfanylphenyl)propanal
• 英文别名: 3-oxo-3-(2-sulfanylphenyl)propanal
• 化学式: C₉H₈O₂S
• 分子量: 180.227
• InChiKey: KOPQNEJAVSVQMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  35.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Oxo-3-(2-sulfanylphenyl)propanal 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以1.1 g的产率得到1-硫代色原酮
  参考文献：
  名称：

  TMSI-Promoted Vinylogous Michael Addition of Siloxyfuran to 2-Substituted Chromones: A General Approach for the Total Synthesis of Chromanone Lactone Natural Products

  摘要：

  A concise and facile synthetic protocol for the construction of the 2-gamma-lactone chromanone skeleton has been achieved through a TMSI-promoted diastereoselective vinylogous Michael addition of siloxyfuran to 2-substituted chromones. The applicability of this method is demonstrated through the rapid access to the total syntheses of (+/-)-microdiplodiasone, (+/-)-lachnone C, and (+/-)-gonytolides C and G.

  DOI：

  10.1021/jo502571r
• 作为产物：
  描述：

  硫代水杨酸 在 sodium 、 lithium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 22.5h， 生成 3-Oxo-3-(2-sulfanylphenyl)propanal
  参考文献：
  名称：

  TMSI-Promoted Vinylogous Michael Addition of Siloxyfuran to 2-Substituted Chromones: A General Approach for the Total Synthesis of Chromanone Lactone Natural Products

  摘要：

  A concise and facile synthetic protocol for the construction of the 2-gamma-lactone chromanone skeleton has been achieved through a TMSI-promoted diastereoselective vinylogous Michael addition of siloxyfuran to 2-substituted chromones. The applicability of this method is demonstrated through the rapid access to the total syntheses of (+/-)-microdiplodiasone, (+/-)-lachnone C, and (+/-)-gonytolides C and G.

  DOI：

  10.1021/jo502571r

文献信息

• TMSI-Promoted Vinylogous Michael Addition of Siloxyfuran to 2-Substituted Chromones: A General Approach for the Total Synthesis of Chromanone Lactone Natural Products
  作者：Jie Liu、Zhanchao Li、Pei Tong、Zhixiang Xie、Yuan Zhang、Ying Li

  DOI：10.1021/jo502571r

  日期：2015.2.6

  A concise and facile synthetic protocol for the construction of the 2-gamma-lactone chromanone skeleton has been achieved through a TMSI-promoted diastereoselective vinylogous Michael addition of siloxyfuran to 2-substituted chromones. The applicability of this method is demonstrated through the rapid access to the total syntheses of (+/-)-microdiplodiasone, (+/-)-lachnone C, and (+/-)-gonytolides C and G.