t-butyl 2-amino-1,2,3,4-tetrahydro-1-hydroxynaphthalene-2-carboxylate | 1381800-95-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: t-butyl 2-amino-1,2,3,4-tetrahydro-1-hydroxynaphthalene-2-carboxylate
• CAS: 1381800-95-8
• 化学式: C₁₅H₂₁NO₃
• 分子量: 263.337
• InChiKey: PVJGKYSWPCBPAF-IUODEOHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.71
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  72.55
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  t-butyl 2-amino-1,2,3,4-tetrahydro-1-hydroxynaphthalene-2-carboxylate 、 3,5-双三氟甲基苯甲酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以81%的产率得到tert-butyl (1R,2R)-2-[[3,5-bis(trifluoromethyl)benzoyl]amino]-1-[3,5-bis(trifluoromethyl)benzoyl]oxy-3,4-dihydro-1H-naphthalene-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
• 作为产物：
  描述：

  tert-butyl (S)-2-chloro-1,2,3,4-tetrahydro-1-oxonaphthalene-2-carboxylate 在 sodium azide 、 20% Pd-BaSO4 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 6.0h， 生成 t-butyl 2-amino-1,2,3,4-tetrahydro-1-hydroxynaphthalene-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