(1S,4R)-N--2,3-oxazabicyclo<2.2.1>hept-5-ene | 160057-06-7

• 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: (1S,4R)-N--2,3-oxazabicyclo<2.2.1>hept-5-ene
• 英文别名: tert-butyl N-[(2S)-1-[(1S,4R)-2-oxa-3-azabicyclo[2.2.1]hept-5-en-3-yl]-1-oxopropan-2-yl]carbamate
• CAS: 160057-06-7
• 化学式: C₁₃H₂₀N₂O₄
• 分子量: 268.313
• InChiKey: GISLZFRMOBUGCC-LPEHRKFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 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：

  (1S,4R)-N--2,3-oxazabicyclo<2.2.1>hept-5-ene 在 disodium hydrogenphosphate 、 sodium amalgam 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 2.0h， 以95%的产率得到cis-(1S,3R)-3-<(N-Boc-L-alanyl)amino>cyclopent-4-enol
  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：

  BOC-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 为溶剂， 反应 1.0h， 生成 (1S,4R)-N--2,3-oxazabicyclo<2.2.1>hept-5-ene
  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

• Rapid syntheses of either enantiomer of important carbocyclic nucleoside precursors
  作者：Brock T Shireman、Marvin J Miller

  DOI：10.1016/s0040-4039(00)01668-3

  日期：2000.12

  The syntheses of both enantiomers of aminocyclopentanetriol 1, a versatile carbocyclic nucleoside precursor, is reported utilizing an amino acid-derived acylnitroso Diels–Alder cycloaddition. The sequence is practical and proceeds in an overall yield of 36% from the d-alanine-derived hydroxamic acid.

  据报道，利用氨基酸衍生的酰基亚硝基Diels-Alder环加成法，合成了一种通用的碳环核苷前体氨基环戊三醇1的两种对映体。该序列是实用的，并且从d-丙氨酸衍生的异羟肟酸的总产率为36％。
• Asymmetric syntheses of novel amino acids and peptides from acylnitroso-derived cycloadducts
  作者：Allen R. Ritter、Marvin J. Miller

  DOI：10.1016/s0040-4039(00)78547-9

  日期：1994.12

  Oxidative cleavage of cycloadducts of amino acid-derived acylnitroso compounds produces peptides in which the carbon framework of the new carboxy terminal amino acid was generated from cyclopentadiene.

  氨基酸衍生的酰基亚硝基化合物的环加合物的氧化裂解产生了这样的肽，其中新的羧基末端氨基酸的碳骨架是由环戊二烯生成的。
• An enantioselective synthesis of the cyclopentene fragment of nucleoside Q
  作者：Kyung-Hee Kim、Marvin J. Miller

  DOI：10.1016/s0040-4039(03)00973-0

  日期：2003.6

  An enantioselective synthesis of (3S,4R,5S)-(+)-3-amino-4.5-dihydroxycyclopentene, a segment of nucleoside Q and Q base. is reported utilizing an amino acid-derived acylnitroso Diels-Alder cycloaddition. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Ritter Allen R., Miller Marvin J., J. Org. Chem, 59 (1994) N 16, S 4602-4611
  作者：Ritter Allen R., Miller Marvin J.

  DOI：——

  日期：——
• 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.