N-(Carbobenzyloxy)-L-alanine 9,10-dimethylanthracene acyl nitroso adduct | 160057-14-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: N-(Carbobenzyloxy)-L-alanine 9,10-dimethylanthracene acyl nitroso adduct
• 英文别名: benzyl N-[(2S)-1-(1,8-dimethyl-15-oxa-16-azatetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaen-16-yl)-1-oxopropan-2-yl]carbamate
• CAS: 160057-14-7
• 化学式: C₂₇H₂₆N₂O₄
• 分子量: 442.514
• InChiKey: HAFGWCPVEMXURW-VVYOJRGZSA-N

物化性质

• 密度：
  1.270±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-环己二烯 、 N-(Carbobenzyloxy)-L-alanine 9,10-dimethylanthracene acyl nitroso adduct 以 苯 为溶剂， 生成 ((R)-1-Methyl-2-(1S,4R)-2-oxa-3-aza-bicyclo[2.2.2]oct-5-en-3-yl-2-oxo-ethyl)-carbamic acid benzyl ester 、 ((R)-1-Methyl-2-(1R,4S)-2-oxa-3-aza-bicyclo[2.2.2]oct-5-en-3-yl-2-oxo-ethyl)-carbamic acid benzyl ester
  参考文献：
  名称：

  Amino Acid-Derived Chiral Acyl Nitroso Compounds: Diastereoselectivity in Intermolecular Hetero Diels-Alder Reactions

  摘要：

  The diastereoselectivities of chiral acyl nitroso dienophiles derived from optically pure N-protected alpha-amino hydroxamic acids have been determined in intermolecular hetero Diels-Alder reactions. The cycloaddition reactions afforded synthetically useful quantities of functionally rich, optically pure cycloadducts, useful for the preparation of a variety of compounds of potential biological interest. Molybdenum hexacarbonyl reduction of the cycloadducts gave optically pure allylic alcohols. Osmium tetraoxide-catalyzed dihydroxylation of several bis-allylically substituted intermediates gave only the diastereomerically pure diols corresponding to naturally occurring 2',3'-dihydroxynucleoside analogs.

  DOI：

  10.1021/jo00095a040
• 作为产物：
  描述：

  Z-L-丙氨酸甲酯 在 氢氧化钾 、 盐酸羟胺 、 四丁基高碘酸铵 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 N-(Carbobenzyloxy)-L-alanine 9,10-dimethylanthracene acyl nitroso adduct
  参考文献：
  名称：

  Amino Acid-Derived Chiral Acyl Nitroso Compounds: Diastereoselectivity in Intermolecular Hetero Diels-Alder Reactions

  摘要：

  The diastereoselectivities of chiral acyl nitroso dienophiles derived from optically pure N-protected alpha-amino hydroxamic acids have been determined in intermolecular hetero Diels-Alder reactions. The cycloaddition reactions afforded synthetically useful quantities of functionally rich, optically pure cycloadducts, useful for the preparation of a variety of compounds of potential biological interest. Molybdenum hexacarbonyl reduction of the cycloadducts gave optically pure allylic alcohols. Osmium tetraoxide-catalyzed dihydroxylation of several bis-allylically substituted intermediates gave only the diastereomerically pure diols corresponding to naturally occurring 2',3'-dihydroxynucleoside analogs.

  DOI：

  10.1021/jo00095a040

文献信息

• Amino Acid-Derived Chiral Acyl Nitroso Compounds: Diastereoselectivity in Intermolecular Hetero Diels-Alder Reactions
  作者：Allen R. Ritter、Marvin J. Miller

  DOI：10.1021/jo00095a040

  日期：1994.8

  The diastereoselectivities of chiral acyl nitroso dienophiles derived from optically pure N-protected alpha-amino hydroxamic acids have been determined in intermolecular hetero Diels-Alder reactions. The cycloaddition reactions afforded synthetically useful quantities of functionally rich, optically pure cycloadducts, useful for the preparation of a variety of compounds of potential biological interest. Molybdenum hexacarbonyl reduction of the cycloadducts gave optically pure allylic alcohols. Osmium tetraoxide-catalyzed dihydroxylation of several bis-allylically substituted intermediates gave only the diastereomerically pure diols corresponding to naturally occurring 2',3'-dihydroxynucleoside analogs.