5,5-dimethyl-3-(2-oxopropyl)tetrahydrofuran-2-one | 1174396-66-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 5,5-dimethyl-3-(2-oxopropyl)tetrahydrofuran-2-one
• 英文别名: 5,5-dimethyl-(2-oxopropyl)oxolan-2-one；5,5-dimethyl-3-(2-oxopropyl)oxolan-2-one
• CAS: 1174396-66-7
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: XXMDDMCGJHBBOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  5,5-dimethyl-3-(2-oxopropyl)tetrahydrofuran-2-one 、 氨基硫脲 在 硫酸 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以80%的产率得到5,5-dimethyl-3-(2-thiosemicarbazonopropyl)tetrahydrofuran-2-one
  参考文献：
  名称：

  Synthesis of 5-substituted 3-(2-oxopropyl)tetrahydrofuran-2-ones and heterocyclic compounds on their base

  摘要：

  Alkylation of ethyl 2-oxotetrahydrofuran-3-carboxylates with 2,3-dichloroprop-1-ene and 3-bromoprop-1-yne gave new 3,5,5-tri- and 3,3,5,5-tetrasubstituted tetrahydrofuran-2-ones which were converted into the corresponding 3-(2-oxopropyl)tetrahydrofuran-2-ones. Reactions of the latter with semicarabazide, thiosemicarbazide, and phenylhydrazine were studied with a view to obtain new heterocyclic lactones.

  DOI：

  10.1134/s1070428008120130
• 作为产物：
  描述：

  5,5-dimethyl-3-(prop-2-yn-1-yl)oxolan-2-one 在 硫酸 、 水 、 mercury(II) sulfate 作用下， 反应 6.0h， 以76%的产率得到5,5-dimethyl-3-(2-oxopropyl)tetrahydrofuran-2-one
  参考文献：
  名称：

  Synthesis of 5-substituted 3-(2-oxopropyl)tetrahydrofuran-2-ones and heterocyclic compounds on their base

  摘要：

  Alkylation of ethyl 2-oxotetrahydrofuran-3-carboxylates with 2,3-dichloroprop-1-ene and 3-bromoprop-1-yne gave new 3,5,5-tri- and 3,3,5,5-tetrasubstituted tetrahydrofuran-2-ones which were converted into the corresponding 3-(2-oxopropyl)tetrahydrofuran-2-ones. Reactions of the latter with semicarabazide, thiosemicarbazide, and phenylhydrazine were studied with a view to obtain new heterocyclic lactones.

  DOI：

  10.1134/s1070428008120130

文献信息

• Synthesis and transformations of 5,5-disubstituted 3-alkenyloxolan-2-ones
  作者：T. V. Kochikyan、M. A. Samvelyan、A. S. Galstyan、V. M. Muzalevskii、V. G. Nenaidenko

  DOI：10.1134/s1070428016050110

  日期：2016.5

  4,4-disubstituted 2-alkenylbutanolides. By oxidation of the latter with hydrogen peroxide and formic acid diololactones were obtained that in conditions of pinacol-pinacolone rearrangement and oxidation with lead tetraacetate afforded formyl- and epoxybutanolides of new structure.

  通过4，4-二取代的2-（乙氧羰基）丁醇化物的烷基化，合成了新的4，4-二取代的2-链烯基-2-（乙氧羰基）丁醇化物，其在碱性水解下形成4，4-二取代的2-链烯基丁醇化物。通过用过氧化氢和甲酸对后者进行氧化，得到了在频哪醇-频哪酮重排和用四乙酸铅氧化的条件下二氟甲内酯，得到了新结构的甲酰基-和环氧丁醇化物。
• Inhibitors of transglutaminases
  申请人：Zedira GmbH

  公开号：US11072634B2

  公开（公告）日：2021-07-27

  The invention relates to the compound of general formula (I) as novel inhibitors of transglutaminases, to methods for producing the inventive compounds, to pharmaceutical compositions containing said inventive compounds and to their use for the prophylaxis and treatment of diseases associated with transglutaminases.

  本发明涉及作为新型转谷氨酰胺酶抑制剂的通式（I）化合物、生产本发明化合物的方法、含有所述本发明化合物的药物组合物以及它们在预防和治疗与转谷氨酰胺酶有关的疾病方面的用途。
• INHIBITORS OF TRANSGLUTAMINASES
  申请人：Zedira GmbH

  公开号：US20190322700A1

  公开（公告）日：2019-10-24

  The invention relates to the compound of general formula (I) as novel inhibitors of transglutaminases, to methods for producing the inventive compounds, to pharmaceutical compositions containing said inventive compounds and to their use for the prophylaxis and treatment of diseases associated with transglutaminases.
• [EN] INHIBITORS OF TRANSGLUTAMINASES<br/>[FR] INHIBITEURS DE TRANSGLUTAMINASES
  申请人：ZEDIRA GMBH

  公开号：WO2018122419A1

  公开（公告）日：2018-07-05

  The invention relates to the compound of general formula (I) as novel inhibitors of transglutaminases, to methods for producing the inventive compounds, to pharmaceutical compositions containing said inventive compounds and to their use for the prophylaxis and treatment of diseases associated with transglutaminases.