1(R)-O-Acetyl-4(S)-cyclopent-2-ene | 160057-20-5

• 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: 1(R)-O-Acetyl-4(S)-cyclopent-2-ene
• 英文别名: [(1R,4S)-4-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]cyclopent-2-en-1-yl] acetate
• CAS: 160057-20-5
• 化学式: C₁₅H₂₄N₂O₅
• 分子量: 312.366
• InChiKey: ONPDCJYUGPGHKZ-WCQGTBRESA-N

物化性质

• 沸点：
  480.016±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.151±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1(R)-O-Acetyl-4(S)-cyclopent-2-ene 在 四氧化锇 、 对甲苯磺酸 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 反应 1.0h， 生成 1(R)-Acetoxy-2(R),3(R)-(isopropylidenedioxy)-4(S)-amino>cyclopentane
  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 吡啶 、 氢氧化钾 、 hexacarbonyl molybdenum 、 盐酸羟胺 、 四丁基高碘酸铵 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 4.0h， 生成 1(R)-O-Acetyl-4(S)-cyclopent-2-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

• 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.
• 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.