t-butyl 2-amino-2,3-dihydro-1-hydroxy-1H-indene-2-carboxylate | 1381800-94-7

• 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: t-butyl 2-amino-2,3-dihydro-1-hydroxy-1H-indene-2-carboxylate
• 英文别名: tert-butyl (1R,2R)-2-amino-1-hydroxy-1,3-dihydroindene-2-carboxylate
• CAS: 1381800-94-7
• 化学式: C₁₄H₁₉NO₃
• 分子量: 249.31
• InChiKey: FHHJIWDIOSHAMP-BXUZGUMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 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 、 sodium azide 、 C₃₄H₂₄N₂O 、 20% Pd-BaSO4 、 copper(II) bis(trifluoromethanesulfonate) 、 sodium hydride 作用下， 以 甲醇 、 二甲基亚砜 、 苯 为溶剂， 反应 20.0h， 生成 t-butyl 2-amino-2,3-dihydro-1-hydroxy-1H-indene-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

文献信息

• Enantioselective α-amination enabled by a BINAM-derived phase-transfer catalyst
  作者：H. M. Nelson、J. S. Patel、H. P. Shunatona、F. D. Toste

  DOI：10.1039/c4sc02494j

  日期：——

  The enantioselective amination of carbonyl derivatives is achieved via phase-transfer of aryldiazonium salts by BINAM-derived phosphoric acids.

  通过BINAM衍生的磷酸实现芳基重氮盐的相转移，实现羰基衍生物的对映选择性氨化。
• Asymmetric construction of quaternary stereocenters by magnesium catalysed direct amination of β-ketoesters using in situ generated nitrosocarbonyl compounds as nitrogen sources
  作者：Biplab Maji、Mahiuddin Baidya、Hisashi Yamamoto

  DOI：10.1039/c4sc01272k

  日期：——

  An oxophilic magnesium salt in combination with a chiral N,N′-dioxide ligand switches the chemoselectivity of an ambident nitrosocarbonyl species to nitrogen for the highly enantioselective α-amination of β-ketoesters.

  一种亲氧镁盐和手性N，N'-二氧化物配体的组合，将一种具有双官能团亚硝基羰基物种的化学选择性切换到氮，实现了对β-酮酯的高对映选择性α-氨基化反应。
• 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
  作者：Kazutaka Shibatomi、Yoshinori Soga、Akira Narayama、Ikuhide Fujisawa、Seiji Iwasa

  DOI：10.1021/ja304806j

  日期：2012.6.20

  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.