t-butyl 2-(benzylthio)-1,2,3,4-tetrahydro-1-oxonaphthalene-2-carboxylate | 1381801-09-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: t-butyl 2-(benzylthio)-1,2,3,4-tetrahydro-1-oxonaphthalene-2-carboxylate
• 英文别名: tert-butyl (2R)-2-benzylsulfanyl-1-oxo-3,4-dihydronaphthalene-2-carboxylate
• CAS: 1381801-09-7
• 化学式: C₂₂H₂₄O₃S
• 分子量: 368.497
• InChiKey: JAXGDJZIZUKELG-JOCHJYFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-吡咯甲酸叔丁酯 在 N-氯代丁二酰亚胺 、 C₃₅H₂₆N₂O₂ 、 copper(II) bis(trifluoromethanesulfonate) 、 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 t-butyl 2-(benzylthio)-1,2,3,4-tetrahydro-1-oxonaphthalene-2-carboxylate
  参考文献：
  名称：

  Highly Enantioselective Chlorination of β-Keto Esters and Subsequent S_N2 Displacement of Tertiary Chlorides: A Flexible Method for the Construction of Quaternary Stereogenic Centers

  摘要：

  Highly enantioselective chlorination of beta-oxo esters and subsequent stereospecific substitution of tertiary chlorides are described. Enantioselective chlorination of beta-keto esters and malonates was performed using a chiral Lewis acid catalyst prepared from Cu(OTf)(2) and the newly developed spirooxazoline ligand 2 to yield the desired a-chlorinated products with high enantioselectivity (up to 98% ee). Nucleophilic substitution of the resulting chlorides proceeded smoothly to afford a variety of chiral molecules such as alpha-amino, alpha-allcylthio, and alpha-fluoro esters, without loss of enantiopurity. The results of X-ray crystallographic analysis proved that Walden inversion occurs at the chlorinated tertiary carbon center. These results supported the fact that the substitution proceeds via an S(N)2 mechanism.

  DOI：

  10.1021/ja304806j