tert-butyl (R)-2-amino-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate | 1381800-93-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: tert-butyl (R)-2-amino-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate
• 英文别名: t-butyl 2-amino-1,2,3,4-tetrahydro-1-oxonaphthalene-2-carboxylate
• CAS: 1381800-93-6
• 化学式: C₁₅H₁₉NO₃
• 分子量: 261.321
• InChiKey: BNBAULOPDRDKRK-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.85
• 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：
  0.47
• 拓扑面积：
  69.39
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  tert-butyl (S)-2-chloro-1,2,3,4-tetrahydro-1-oxonaphthalene-2-carboxylate 在 sodium azide 、 10 % Pd-BaSO4 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 生成 tert-butyl (R)-2-amino-1-oxo-1,2,3,4-tetrahydronaphthalene-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

• Flexible Stereoselective Functionalizations of Ketones through Umpolung with Hypervalent Iodine Reagents
  作者：Pushpak Mizar、Thomas Wirth

  DOI：10.1002/anie.201400405

  日期：2014.6.2

  The functionalization of carbonyl compounds in the α‐position has gathered much attention as a synthetic route because of the wide biological importance of such products. Through polarity reversal, or “umpolung”, we show here that typical nucleophiles, such as oxygen, nitrogen, and even carbon nucleophiles, can be used for addition reactions after tethering them to enol ethers. Our findings allow novel

  由于此类产品具有广泛的生物学重要性，因此羰基化合物在α位上的功能化作为合成途径已引起广泛关注。通过极性反转或“极性”，我们在这里表明典型的亲核试剂，例如氧，氮，甚至碳亲核试剂，在将它们束缚到烯醇醚后，可以用于加成反应。我们的发现可以进行新颖的逆合成规划，并可以快速组装以前只能通过多步序列访问的结构。