(1R,4S)-N--2,3-oxazabicyclo<2.2.1>hept-5-ene | 160167-61-3

• 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: (1R,4S)-N--2,3-oxazabicyclo<2.2.1>hept-5-ene
• 英文别名: tert-butyl N-[(2S)-1-[(1R,4S)-2-oxa-3-azabicyclo[2.2.1]hept-5-en-3-yl]-1-oxopropan-2-yl]carbamate
• CAS: 160167-61-3
• 化学式: C₁₃H₂₀N₂O₄
• 分子量: 268.313
• InChiKey: GISLZFRMOBUGCC-AEJSXWLSSA-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：

  (1R,4S)-N--2,3-oxazabicyclo<2.2.1>hept-5-ene 在 palladium on activated charcoal sodium tetrahydroborate 、 四氧化锇 、 N-甲基吲哚酮 、 氢气 、 sodium carbonate 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 49.0h， 生成 (3S,4R,5S)-3-tert-butoxycarbonylamino-4,5-isopropylidenedioxycyclopent-1-ene
  参考文献：
  名称：

  An enantioselective synthesis of the cyclopentene fragment of nucleoside Q

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(03)00973-0
• 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 (1R,4S)-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％。
• Synthesis of enantiomerically pure 5'-aza-noraristeromycin analogs
  作者：Arun Ghosh、Allen R. Ritter、Marvin J. Miller

  DOI：10.1021/jo00123a015

  日期：1995.9

  The synthesis of a novel class of enantiomerically pure azanoraristeromycins is described. An asymmetric hetero Diels-Alder reaction using amino acid-derived chiral acylnitroso dienophiles 2 was used to prepare optically pure allylic acetate substrate 10. The palladium(0)-catalyzed addition of the sodium salt of adenine to optically pure acetate 10 was achieved to give N-9-alkylated adenine adduct 11 in good yield. Catalytic osmium tetraoxide dihydroxylation of the didehydro analog provided both diol products 17 and 18, corresponding to common natural and unnatural nucleosides, respectively.
• 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：——
• Oxazoline formation via a palladium-catalyzed cyclization: A direct, stereoselective approach to cis-5-amino-2-cyclopenten-1-ol derivatives
  作者：Jan-Gerd Hansel、Shannon O'Hogan、Stephan Lensky、Allen R. Ritter、Marvin J. Miller

  DOI：10.1016/0040-4039(95)00465-o

  日期：1995.4

  Alanyl substituted 4-amino-2-cyclopenten-1-yl acetates were obtained optically pure in three steps from cyclopentadiene. The Pd-0 catalyzed cyclization of these allylic acetates was studied using protected and unprotected derivatives. A novel oxazoline synthesis was developed and its utility was demonstrated by the preparation of a cis-5-amino-2-cyclopenten-1-ol derivative.
• 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.