methyl 3-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)-2-((R)-1,1-dimethylethylsulfinamido)propanoate | 1173933-54-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 3-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)-2-((R)-1,1-dimethylethylsulfinamido)propanoate
• 英文别名: methyl (2S)-2-[[(R)-tert-butylsulfinyl]amino]-3-(2,2-dimethyl-6-oxo-1,3-dioxin-4-yl)propanoate
• CAS: 1173933-54-4
• 化学式: C₁₄H₂₃NO₆S
• 分子量: 333.406
• InChiKey: JADFTWIRULMUDN-MLMJSJRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  methyl 2-[(R)-tert-butylsulfinyl]iminoacetate 、 (2,2-dimethyl-6-methylene-6H-1,3-dioxin-4-yloxy)trimethylsilane 在 zinc trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 48.5h， 生成 methyl 2-((R)-1,1-dimethylethylsulfinamido)-2-(2,2,6-trimethyl-4-oxo-4H-1,3-dioxin-5-yl)acetate 、 methyl 3-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)-2-((R)-1,1-dimethylethylsulfinamido)propanoate 、 methyl 3-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)-2-((R)-1,1-dimethylethylsulfinamido)propanoate
  参考文献：
  名称：

  Tunable and Highly Regio- and Diastereoselective Vinylogous Mannich-Type Reaction of Dioxinone-Derived Silyl Dienolate

  摘要：

  A tunable and highly regio- and diastereoselective vinylogous Mannich-type reaction of dioxinone-derived silyl dienolate (1) with chiral N-tert-butanesulfinyl imino ester (2) was developed. By appropriate choice of Lewis acid catalyst, two diastereomers of the gamma-product were obtained, respectively, with dr up to 95:5. The procedure for the Ag(I)-catalyzed vinylogous Mannich-type reaction also provided facile access to the alpha-regioisomer with excellent diastereoselectivities (up to > 99:1 dr) by changing the counterion of the Ag(I) salt.

  DOI：

  10.1021/jo900977y

文献信息

• Tunable and Highly Regio- and Diastereoselective Vinylogous Mannich-Type Reaction of Dioxinone-Derived Silyl Dienolate
  作者：Chun-Ling Gu、Li Liu、Dong Wang、Yong-Jun Chen

  DOI：10.1021/jo900977y

  日期：2009.8.7

  A tunable and highly regio- and diastereoselective vinylogous Mannich-type reaction of dioxinone-derived silyl dienolate (1) with chiral N-tert-butanesulfinyl imino ester (2) was developed. By appropriate choice of Lewis acid catalyst, two diastereomers of the gamma-product were obtained, respectively, with dr up to 95:5. The procedure for the Ag(I)-catalyzed vinylogous Mannich-type reaction also provided facile access to the alpha-regioisomer with excellent diastereoselectivities (up to > 99:1 dr) by changing the counterion of the Ag(I) salt.