(S)-O-(tert-butyl)-N-(1-(naphthalen-1-yl)ethyl)hydroxylamine ((1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonate | 1177266-31-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-O-(tert-butyl)-N-(1-(naphthalen-1-yl)ethyl)hydroxylamine ((1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonate
• 英文别名: (S)-N-1-(1'-naphthyl)ethyl-O-tert-butylhydroxylamine (+)-camphorsulfonic acid salt
• CAS: 1177266-31-7
• 化学式: C₁₀H₁₆O₄S*C₁₆H₂₁NO
• 分子量: 475.649
• InChiKey: JUCLGMCKVJOLKA-MNHPXDJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.49
• 重原子数：
  33.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  92.7
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-O-(tert-butyl)-N-(1-(naphthalen-1-yl)ethyl)hydroxylamine ((1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonate 在 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 hexanes 、 二氯甲烷 为溶剂， 反应 14.5h， 生成 (S)-N-tert-butoxy-N-1'-(1''-naphthyl)ethyl (R,R)-3-[N-benzyl-N-(α-methylbenzyl)amino]butanamide
  参考文献：
  名称：

  双不对称感应作为机械探针：对映纯α，β-不饱和酯和对映纯α，β-不饱和异羟肟酸酯的双非对映选择性共轭加成对映体纯的锂酰胺

  摘要：

  将N-苄基-N-（α-甲基苄基）锂的对映体双非对映选择性共轭加成到一系列对映纯α，β-不饱和酯[源自Corey's 8-苯基薄荷醇手性助剂]和对映纯α，β-不饱和异羟肟酸盐[源自我们的“手性Weinreb酰胺”辅助（小号） - ñ -1-（1'-萘基）乙基- ø -叔-butylhydroxylamine]已被用作一种机械探针，以确定这些受体的活性构象。

  DOI：

  10.1016/j.tet.2011.05.102
• 作为产物：
  描述：

  N-[1-(1'-naphthyl)ethyl]-O-tert-butylhydroxylamine 、 camphor-10-sulfonic acid 以 丙酮 为溶剂， 反应 12.0h， 以32.9 g的产率得到(S)-O-(tert-butyl)-N-(1-(naphthalen-1-yl)ethyl)hydroxylamine ((1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonate
  参考文献：
  名称：

  The Chiral Auxiliary N-1-(1′-Naphthyl)ethyl-O-tert-butylhydroxylamine: A Chiral Weinreb Amide Equivalent

  摘要：

  The chiral auxiliary N-1-(1'-naphthyl)ethyl-O-tert-butylhydroxylamine is readily prepared from N-hydroxyphthalimide in four steps, with resolution giving access to both enantiomers in >98% ee, on a multigram (>25 g) scale. Conversion to a range of N-acyl derivatives, followed by highly diastereoselective alkylation (>= 94% de) gives the corresponding chiral, 2-substituted derivatives as single diastereoisomers (>98% de) after chromatography. Reductive cleavage with LlAlH(4) allows direct access to chiral aldehydes, and treatment with MeLi gives chiral methyl ketones in excellent enantiopurity (>= 94% ee). The auxiliary can be recovered in >98% ee and recycled.

  DOI：

  10.1021/ol901174t

文献信息

• Solid state conformations of α,β-unsaturated hydroxamates derived from the ‘chiral Weinreb amide’ auxiliary ( S )- N -1-(1′-naphthyl)ethyl- O - tert -butylhydroxylamine
  作者：Stephen G. Davies、James A. Lee、Paul M. Roberts、James E. Thomson、Jingda Yin

  DOI：10.1016/j.tetasy.2017.07.009

  日期：2017.10

  alpha,beta-Unsaturated hydroxamates derived from the 'chiral Weinreb amide' auxiliary (S)-N-1-(1'-naphthyl) ethyl-O-tert-butylhydroxylamine consistently adopt a defined conformation and undergo highly diastereoselective conjugate addition reactions with lithium amide reagents. The configuration of the N-1-(1'-naphthyl)ethyl group dictates the position of the O-tert-butyl group and also the configuration adopted by the pyramidal nitrogen atom via a 'chiral relay' effect. Conjugate addition of lithium amide reagents to these substrates proceeds on the face opposite to both the O-tert-butyl group and nitrogen lone-pair with high levels of diastereoselectivity. (C) 2017 Elsevier Ltd. All rights reserved.