乙基1-氨基-2-环戊烯-1-羧酸酯 | 541506-73-4

• 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
• 中文名称: 乙基1-氨基-2-环戊烯-1-羧酸酯
• 英文名称: Ethyl 1-aminocyclopent-2-ene-1-carboxylate
• CAS: 541506-73-4
• 化学式: C₈H₁₃NO₂
• 分子量: 155.197
• InChiKey: SMXHSKTVWSWOTL-UHFFFAOYSA-N

物化性质

• 沸点：
  206.2±40.0 °C(Predicted)
• 密度：
  1.091±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2922499990

反应信息

• 作为反应物：
  描述：

  乙基1-氨基-2-环戊烯-1-羧酸酯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 144.0h， 生成 (+/-)-ethyl N-di-tert-butoxycarbonyl-1-amino-cyclopent-2-ene-1-carboxylate
  参考文献：
  名称：

  Synthesis and biological evaluation of new amino acids structurally related to the antitumor agent acivicin

  摘要：

  A set of racemic conformationally constrained analogues of the antitumor antibiotic acivicin (+)-1 has been prepared through a strategy based on 1,3-dipolar cycloaddition of bromonitrile oxide to suitable dipolarophiles. The bromo analogue (2) of acivicin was also synthesized and tested as a reference compound, together with its stereoisomer 3. The antitumor properties of novel amino acids 4-7 were evaluated in vitro against human tumor cell lines. Their efficacy to inhibit glutamate synthase (GltS) from Azospirillum brasilense was also assayed. None of the studied compounds, but 2, showed significant activity.

  DOI：

  10.1016/s0014-827x(03)00107-1
• 作为产物：
  描述：

  Cyclopentanon-(2)-dicarbonsaeure-(1,1)-diaethylester 在 盐酸 、 sodium hydroxide 、 sodium tetrahydroborate 、 sodium azide 、 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 、 乙醇 、 二氯甲烷 、 水 、 丙酮 、 甲苯 、 苯 为溶剂， 反应 68.5h， 生成 乙基1-氨基-2-环戊烯-1-羧酸酯
  参考文献：
  名称：

  新型构象限制的谷氨酸类似物的设计

  摘要：

  立体异构3-羧基- Δ 2 -isoxazoline环戊烷氨基酸，其代表谷氨酸的限制构象，已经通过基于ethoxycarbonylformonitrile氧化物的1,3-偶极环加成到一个适当保护的1-氨基-环戊的策略制备2-烯基羧酸。在iGluRs和mGluRs处检测到的这些氨基酸被证明是无活性的。所述生物数据已占到通过它们的构象轮廓与一个3-羧基- Δ的比较2 -isoxazolinyl脯氨酸（CIP-A）和（±）-1-氨基环戊烷-1,3-二羧酸。

  DOI：

  10.1016/s0040-4020(03)00079-6

文献信息

• Design of novel conformationally restricted analogues of glutamic acid
  作者：Paola Conti、Marco De Amici、Gabriella Roda、Giulio Vistoli、Tine Bryan Stensbøl、Hans Bräuner-Osborne、Ulf Madsen、Lucio Toma、Carlo De Micheli

  DOI：10.1016/s0040-4020(03)00079-6

  日期：2003.2

  represent restricted conformations of glutamic acid, have been prepared through a strategy based on the 1,3-dipolar cycloaddition of ethoxycarbonylformonitrile oxide to a suitably protected 1-amino-cyclopent-2-enecarboxylic acid. These amino acids, assayed at iGluRs and mGluRs, proved to be inactive. The biological data have been accounted for through the comparison of their conformational profile with that

  立体异构3-羧基- Δ 2 -isoxazoline环戊烷氨基酸，其代表谷氨酸的限制构象，已经通过基于ethoxycarbonylformonitrile氧化物的1,3-偶极环加成到一个适当保护的1-氨基-环戊的策略制备2-烯基羧酸。在iGluRs和mGluRs处检测到的这些氨基酸被证明是无活性的。所述生物数据已占到通过它们的构象轮廓与一个3-羧基- Δ的比较2 -isoxazolinyl脯氨酸（CIP-A）和（±）-1-氨基环戊烷-1,3-二羧酸。
• Synthesis and biological evaluation of new amino acids structurally related to the antitumor agent acivicin
  作者：Paola Conti、Gabriella Roda、Helena Stabile、Maria Antonietta Vanoni、Bruno Curti、Marco De Amici

  DOI：10.1016/s0014-827x(03)00107-1

  日期：2003.9

  A set of racemic conformationally constrained analogues of the antitumor antibiotic acivicin (+)-1 has been prepared through a strategy based on 1,3-dipolar cycloaddition of bromonitrile oxide to suitable dipolarophiles. The bromo analogue (2) of acivicin was also synthesized and tested as a reference compound, together with its stereoisomer 3. The antitumor properties of novel amino acids 4-7 were evaluated in vitro against human tumor cell lines. Their efficacy to inhibit glutamate synthase (GltS) from Azospirillum brasilense was also assayed. None of the studied compounds, but 2, showed significant activity.