[1S-cis]-4-amino-2-cyclopenten-1-ol | 220354-28-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [1S-cis]-4-amino-2-cyclopenten-1-ol
• 英文别名: (1S,4R)-4-aminocyclopent-2-en-1-ol
• CAS: 220354-28-9
• 化学式: C₅H₉NO
• 分子量: 99.1326
• InChiKey: NPHHAQOEPZJMNE-CRCLSJGQSA-N

物化性质

• 沸点：
  187.8±40.0 °C(Predicted)
• 密度：
  1.145±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [1S-cis]-4-amino-2-cyclopenten-1-ol 在 Candida antarctica lipase 、 甲基叔丁基醚 、 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 反应 33.0h， 生成 (1R,4S)-乙酸-4-叔丁氧羰基氨基-环戊基-2-烯酯
  参考文献：
  名称：

  Enzymatic Resolution of Aminocyclopentenols as Precursors to d- and l-Carbocyclic Nucleosides

  摘要：

  Racemic cis-4-aminocyclopent-2-en-1-ols were synthesized in three steps utilizing hetero Diels-Alder chemistry. Starting from suitably protected hydroxylamines, oxidization with sodium periodate and trapping with cyclopentadiene afforded cycloadducts (+/-)-5a-d. The N-O bond of the cycloadducts was reduced with Mo(CO)(6) to afford (+/-)-cis-4-aminocyclopent-2-en-1-ols (+/-)-6a-d. These compounds, or their corresponding acetates, were kinetically resolved by enzymatic acetylation or hydrolysis, respectively. Enzymatic acetylation of cis-N-(benzylcarbamoyl)-4-aminocyclopent-2-enol [(+/-)-6a] with Candida antarctica B lipase and Pseudomonas species lipase gave the corresponding acetate (-)-7a in 90% and 92% ee, respectively, after 40% conversion. Enzymatic hydrolysis of cis-N-acetyl-4-aminocyclopent-2-enol 1-O-acetate (+/-)-7d with electric eel acetylcholine esterase was successful in providing both cis-N-acetyl-4-aminocyclopent-2-enols (+)ed and (+)-7d in 92% ee (99% ee after a single recrystallization) after 40% conversion. Further synthetic transformations of these resolved synthetic building blocks and derivatives are also reported.

  DOI：

  10.1021/jo972265a
• 作为产物：
  描述：

  (1S,4R)-2-oxa-3aza-bicyclo[2,2,1]hept-5-ene hydrochloride 在 溶剂黄146 、 锌 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 [1S-cis]-4-amino-2-cyclopenten-1-ol
  参考文献：
  名称：

  环戊二烯与亚硝基衍生物之间的手性Diels-Alder反应：加合物的热异构化/消旋化

  摘要：

  从d-甘露糖和d-核糖系列的手性氯亚硝基衍生物4和5分别以高收率和良好的对映异构体合成环戊二烯亚硝基加合物1a和ent - 1a。这些加合物的热消旋作用发生在室温以下。制备了其他一些手性Diels-Alder亚硝基加合物，分别为d-扁桃，l-脯氨醇和d- O-甲基脯氨醇，并根据N取代对它们进行了热异构化。从ent - 1a提出了手性酰胺基-环戊烯醇（+）- 2b（一种重要的生物有趣化合物的简单前体）的简单合成方法。

  DOI：

  10.1016/j.tetasy.2012.09.005

文献信息

• 1,2,3-triazolo[4,5-d]pyrimidines as P2T receptor antagonists
  申请人：AstraZeneca UK Limited

  公开号：US06251910B1

  公开（公告）日：2001-06-26

  Compounds of formula having the following stereochemistry wherein R, R1, R2, R3 and R4 are as defined in the specification. The compounds are useful as P2T receptor antagonists.

  具有以下立体化学的式化合物 其中R、R1、R2、R3和R4如规范中所定义。这些化合物可用作P2T受体拮抗剂。
• Novel compounds
  申请人：——

  公开号：US20040023988A1

  公开（公告）日：2004-02-05

  The invention provides novel 1,2,3-triazolo[4,5-d]pyrimidine compounds, their use as medicaments, compositions containing them and processes for their preparation.

  这项发明提供了新颖的1,2,3-三唑[4,5-d]嘧啶化合物，它们作为药物的用途，含有它们的组合物以及它们的制备方法。
• Diastereoselective [4+2] Cycloadditions of Acyl Nitroso Compounds
  作者：Stephen F. Martin、Michael Hartmann、John A. Josey

  DOI：10.1016/s0040-4039(00)92508-5

  日期：1992.6

  A highly diastereoselective route to unsaturated amino alcohol derivatives has been developed that features the [4+2] cycloaddition of chiral acyl nitroso compounds to a variety of conjugated dienes; a useful oxidative method for generating acyl nitroso compounds from the corresponding hydroxamic acids under very mild conditions was also discovered.

  已经开发出一种高度非对映选择性的不饱和氨基醇衍生物的方法，其特征是将手性酰基亚硝基化合物[4 + 2]环加成到各种共轭二烯上。还发现了一种在非常温和的条件下由相应的异羟肟酸生成酰基亚硝基化合物的有用的氧化方法。