(2-oxocyclopent-3-en-1-yl) acetate | 70919-20-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-oxocyclopent-3-en-1-yl) acetate
• 英文别名: (+/-)-5-acetoxy-2-cyclopentenone；5-acetoxy-2-cyclopentenone；5-acetoxycyclopentenone；5-Acetoxy-cyclopenten-(2)-on-(1)；2-Acetoxycyclopenten-2-on-1；5-Acetoxycyclopentenon
• CAS: 70919-20-9
• 化学式: C₇H₈O₃
• 分子量: 140.139
• InChiKey: IAQZQUFZWSAUCE-UHFFFAOYSA-N

物化性质

• 沸点：
  223.0±40.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2-oxocyclopent-3-en-1-yl) acetate 在 ammonium sulfate 、 phosphate buffer 、 pig liver esterase 作用下， 反应 5.0h， 以45%的产率得到(S)-(+)-5-acetoxy-2-cyclopentenone
  参考文献：
  名称：

  Chemoenzymatic synthesis of α′- and α-acetoxylated cyclic ketones

  摘要：

  alpha,beta-Unsaturated and saturated cyclic ketones were selectively oxidized at the alpha'- and alpha-positions using Mn(OAc)(3) and Pb(OAc)(4), respectively, resulting in high chemical yields. The resultant racemic alpha'- and alpha-acetoxylated substrates were resolved into corresponding enantiomerically enriched alpha'- and alpha-hydroxylated and acetoxylated compounds with 96-98% ee via PLE hydrolysis. The absolute configurations of alpha'-acetoxy-alpha,beta-unsaturated cyclic ketones were determined by transforming them into the corresponding saturated alpha-acetoxy cyclic ketones of known absolute configuration. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.04.019
• 作为产物：
  描述：

  2-环戊烯酮 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 、 溶剂黄146 为溶剂， 生成 (2-oxocyclopent-3-en-1-yl) acetate
  参考文献：
  名称：

  Hafner,K.; Goliasch,K., Chemische Berichte, 1961, vol. 94, p. 2909 - 2921

  摘要：

  DOI：

文献信息

• [EN] 1 -OXO-1,2-DIHYDROISOQUINOLIN-7-YL-(5-SUBSTITUTED-THIOPHEN-2-YL)-SULFONAMIDE COMPOUNDS, FORMULATIONS CONTAINING THOSE COMPOUNDS, AND THEIR USE AS AICARFT INHIBITORS IN THE TREATMENT OF CANCERS<br/>[FR] COMPOSÉS 1-OXO-1,2-DIHYDROISOQUINOLÉINE-7-YL-(5-SUBSTITUÉ-THIOPHÉN-2-YL)-SULFONAMIDE, FORMULATIONS CONTENANT CES COMPOSÉS ET LEUR UTILISATION COMME INHIBITEURS D'AICARFT DANS LE TRAITEMENT DE CANCERS
  申请人：LILLY CO ELI

  公开号：WO2016089670A1

  公开（公告）日：2016-06-09

  1-Oxo-1,2-dihydroisoquinolin-7-yl-(5-substituted-thiophen-2-yl)-sulfonamide compounds, formulations containing those compounds, and their use as AICARFT inhibitors.

  1-Oxo-1,2-二氢异喹啉-7-基-(5-取代噻吩-2-基)-磺酰胺化合物，含有这些化合物的配方，以及它们作为AICARFT抑制剂的用途。
• Arginase Inhibitors and Their Therapeutic Applications
  申请人：OncoArendi Therapeutics S.A.

  公开号：US20170319536A1

  公开（公告）日：2017-11-09

  Disclosed are small molecule therapeutic compounds that are potent inhibitors of arginase 1 and arginase 2 activity. Also disclosed are pharmaceutical compositions comprising the compounds, and methods for using the compounds for treating or preventing a disease or condition associated with arginase activity.

  揭示了一种小分子治疗化合物，它们是较强的精氨酸酶1和精氨酸酶2活性抑制剂。还揭示了包含这些化合物的药物组合物，以及使用这些化合物治疗或预防与精氨酸酶活性相关的疾病或状况的方法。
• New organofluorine building blocks: inhibition of the malarial aspartic proteases plasmepsin II and IV by alicyclic α,α-difluoroketone hydrates
  作者：Christoph Fäh、Leo A. Hardegger、Lukas Baitsch、W. Bernd Schweizer、Solange Meyer、Daniel Bur、François Diederich

  DOI：10.1039/b908489d

  日期：——

  therapeutic agents against malaria has become urgent during the past few decades, due to an increased prevalence of drug-resistant strains of malaria-causing Plasmodium parasites. Possible targets are the hemoglobin-degrading aspartic proteases, the plasmepsins. While acyclic α,α-difluoroketone hydrates have been introduced into peptidomimetics to bind to the catalytic Asp dyad of aspartic proteases, alicyclic

  在过去的几十年中，由于引起疟疾的疟原虫寄生虫的耐药菌株的流行增加，抗疟疾的新治疗剂的开发已变得迫在眉睫。可能的靶标是降解血红蛋白的天冬氨酸蛋白酶，即纤溶酶。尽管无环α，α-二氟酮水合物已被引入拟肽中以与天冬氨酸蛋白酶的催化Asp二元结合，但脂环族衍生物仍是未知的。本文描述了水合脂环族α，α-二氟环戊酮和-环己酮的通用合成方法，并用适当的取代基修饰以填充酶活性位点的S1 / S3和“翻盖”袋。对它们的生物活性针对纤溶酶II和IV进行了测试，显示出IC 50最佳配体的最大分子量（观察到最大初始速度的50％的抑制剂浓度）为7μM。具有质子化仲铵中心以解决催化二元体的参考抑制剂显示相似的结合亲和力。环状α，α-二氟酮水合物的X射线晶体结构揭示了这些新型构件参与H键网络的能力。还研究了溶液中二氟酮的水合。一项示例性研究表明，α，α-二氟环己酮的水合平衡常数远高于相应的环戊酮。
• Enantioselective epoxidation of cyclic 1,3-dienes catalyzed by a sterically and electronically optimized (salen)Mn complex
  作者：Sukbok Chang、Richard M Heid、Eric N Jacobsen

  DOI：10.1016/s0040-4039(00)75786-8

  日期：1994.1

  Chiral (salen)Mn(III)Cl complexes catalyze epoxidation of cyclic 1,3-dienes with moderate-to-good enantioselectivity. A new catalyst (2), bearing sterically hindered and electron donating OSi(iPr)3 (OTIPS) substituents, induces up to 12% higher selectivity than the previously-reported tert-butyl substituted analog 1.

  手性（salen）Mn（III）Cl络合物以中等至良好的对映选择性催化环状1,3-二烯的环氧化。一种新的催化剂（2）带有空间位阻和给电子的OSi（i Pr）3（OTIPS）取代基，其选择性比以前报道的叔丁基取代的类似物1高12％。
• Chemoenzymatic synthesis of enantiomerically enriched 2-oxobicyclo[m.1.0]alkan-3-yl acetate derivatives
  作者：Fazilet Devrim Özdemirhan、Murat Çelik、Selin Atlı、Cihangir Tanyeli

  DOI：10.1016/j.tetasy.2006.01.004

  日期：2006.1

  α′-acetoxy α,β-unsaturated cyclopentanone and cyclohexanone have been resolved into the corresponding enantiomerically enriched α′-hydroxylated and acetoxylated compounds with 96–97% ee via PLE hydrolysis. Stereoselectivity in the palladium(II)-catalyzed reaction between the enantiomerically enriched α′-acetoxylated compounds and diazomethane has been investigated. In the α′-acetoxylated cyclopentenone

  外消旋的α'-乙酰氧基α，β-不饱和环戊酮和环己酮已通过PLE水解分解为相应的对映体富集的具有96-97％ee的α'-羟基化和乙酰氧基化的化合物。研究了对映体富集的α'-乙酰氧基化化合物与重氮甲烷之间在钯（II）催化反应中的立体选择性。在α'-乙酰氧基化的环戊烯酮中，优先的环丙烷化反应以反形式发生，而α'-乙酰氧基化的环己烯酮提供顺式和反式产物（syn：anti，61：36％）。通过NOE实验确定产物的相对构型。