benzyl 2-(tert-butoxycarbonylamino)-3-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)propanoate | 1173933-63-5

• 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: benzyl 2-(tert-butoxycarbonylamino)-3-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)propanoate
• 英文别名: benzyl (2R)-3-(2,2-dimethyl-6-oxo-1,3-dioxin-4-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 1173933-63-5
• 化学式: C₂₁H₂₇NO₇
• 分子量: 405.448
• InChiKey: DLJBZLPYLDMBFX-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzyl 2-(tert-butoxycarbonylamino)-3-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)propanoate 以 甲苯 为溶剂， 反应 1.5h， 以65%的产率得到(R)-2-benzyl 1-tert-butyl 4,6-dioxopiperidine-1,2-dicarboxylate
  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
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 benzyl 3-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)-2-((R)-1,1-dimethylethylsulfinamido)propanoate 在 盐酸 、 甲醇 、 水 、 碘 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 3.0h， 以90%的产率得到benzyl 2-(tert-butoxycarbonylamino)-3-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)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