ethyl 3-chloro-2-(4-methylphenylsulfonamido)-4-(naphthalen-2-yl)-4-oxobutanoate | 1283749-02-9

• 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: ethyl 3-chloro-2-(4-methylphenylsulfonamido)-4-(naphthalen-2-yl)-4-oxobutanoate
• 英文别名: ethyl (2R,3R)-3-chloro-2-[(4-methylphenyl)sulfonylamino]-4-naphthalen-2-yl-4-oxobutanoate
• CAS: 1283749-02-9
• 化学式: C₂₃H₂₂ClNO₅S
• 分子量: 459.95
• InChiKey: VLZGDBGSACWYAY-RTWAWAEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  97.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  二氯胺T 、 ethyl 4-(naphthalen-2-yl)-4-oxobut-2-enoate 、 对甲苯磺酰胺 在 (1R,2S)-N-(1-adamantyl)-1-[3-[(1R,2S)-2-(1-adamantylcarbamoyl)-1-oxidopiperidin-1-ium-1-yl]propyl]-1-oxidopiperidin-1-ium-2-carboxamide 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以96%的产率得到ethyl 3-chloro-2-(4-methylphenylsulfonamido)-4-(naphthalen-2-yl)-4-oxobutanoate
  参考文献：
  名称：

  Catalytic Asymmetric Chloroamination Reaction of α,β-Unsaturated γ-Keto Esters and Chalcones

  摘要：

  Highly efficient catalytic chloroamination reaction of alpha,beta-unsaturated gamma-keto esters and chalcones has been developed via a chloronium-based mechanism to deliver anti-regioselective vicinal chloroamines instead of the aziridinium intermediates delivered aminochlorides. The combination of TsNCl2 and TsNH2 as reagents made the transformation highly efficient, delivering the gamma-carbonyl-beta-chloro-alpha-amino acid derivatives and alpha-chloro-beta-amino-ketone derivatives in nearly quantitative yields with up to 99% ee and 99:1 dr under 0.05-0.5 mol % catalyst loading. TsNHCl was demonstrated to act as the key reactive species to form a bridged chloronium ion intermediate in the presence of a chiral scandium complex. The method might provide useful information for further realization of other haloamination reactions.

  DOI：

  10.1021/ja110668c

文献信息

• Catalytic Asymmetric Chloroamination Reaction of α,β-Unsaturated γ-Keto Esters and Chalcones
  作者：Yunfei Cai、Xiaohua Liu、Jun Jiang、Weiliang Chen、Lili Lin、Xiaoming Feng

  DOI：10.1021/ja110668c

  日期：2011.4.20

  Highly efficient catalytic chloroamination reaction of alpha,beta-unsaturated gamma-keto esters and chalcones has been developed via a chloronium-based mechanism to deliver anti-regioselective vicinal chloroamines instead of the aziridinium intermediates delivered aminochlorides. The combination of TsNCl2 and TsNH2 as reagents made the transformation highly efficient, delivering the gamma-carbonyl-beta-chloro-alpha-amino acid derivatives and alpha-chloro-beta-amino-ketone derivatives in nearly quantitative yields with up to 99% ee and 99:1 dr under 0.05-0.5 mol % catalyst loading. TsNHCl was demonstrated to act as the key reactive species to form a bridged chloronium ion intermediate in the presence of a chiral scandium complex. The method might provide useful information for further realization of other haloamination reactions.