(5,5-二甲基-2-氧代四氢呋喃-3-基)-乙酸 | 412298-86-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 中文名称: (5,5-二甲基-2-氧代四氢呋喃-3-基)-乙酸
• 英文名称: 2-(5,5-dimethyl-2-oxotetrahydrofuran-3-yl)acetic acid
• 英文别名: 2-carboxymethyl-4-methyl-4-pentanolide；(5,5-dimethyl-2-oxo-tetrahydro-[3]furyl)-acetic acid；(5,5-Dimethyl-2-oxo-tetrahydro-[3]furyl)-essigsaeure；(5,5-dimethyl-2-oxotetrahydrofuran-3-yl)acetic acid；(5,5-Dimethyl-2-oxo-tetrahydro-furan-3-yl)-acetic acid；2-(5,5-dimethyl-2-oxooxolan-3-yl)acetic acid
• CAS: 412298-86-3
• 化学式: C₈H₁₂O₄
• mdl: MFCD01549292
• 分子量: 172.181
• InChiKey: XDUMFQUFEARYLP-UHFFFAOYSA-N

物化性质

• 熔点：
  141-143 °C
• 沸点：
  140-180 °C(Press: 2 Torr)
• 密度：
  1.172±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2932209090

反应信息

• 作为反应物：
  描述：

  (5,5-二甲基-2-氧代四氢呋喃-3-基)-乙酸 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 苯 为溶剂， 生成 4-methyl-2-(1-thiosemicarbazidocarbonyl)-4-pentanolide
  参考文献：
  名称：

  摘要：

  Alkylation of 2-ethoxycarbonyl-4-pentanol ides with ethyl chloroacetate gave 2-ethoxycarbonyl-2 ethoxycarbonylmethyl-4-pentanolides. Alkaline hydrolysis of the latter afforded 2-carboxymethyl-4-pentanolides which were converted into the corresponding acyl chlorides in high yield by treatment with thionyl chloride in the presence of a catalytic amount of dimethylformamide. Reaction of 2-chloroformylmethyl-4-pentanolides with thiosemicarbazide, followed by treatment with alkali, resulted in formation of 2-(5-mercapto-1,2,4-triazol-3-ylmethyl)-4-pentanolides.

  DOI：

  10.1023/a:1016338226670
• 作为产物：
  描述：

  2-ethoxycarbonyl-2-ethoxycarbonylmethyl-4-methylpentanolide 在 sodium hydroxide 、 水 作用下， 以90%的产率得到(5,5-二甲基-2-氧代四氢呋喃-3-基)-乙酸
  参考文献：
  名称：

  摘要：

  Alkylation of 2-ethoxycarbonyl-4-pentanol ides with ethyl chloroacetate gave 2-ethoxycarbonyl-2 ethoxycarbonylmethyl-4-pentanolides. Alkaline hydrolysis of the latter afforded 2-carboxymethyl-4-pentanolides which were converted into the corresponding acyl chlorides in high yield by treatment with thionyl chloride in the presence of a catalytic amount of dimethylformamide. Reaction of 2-chloroformylmethyl-4-pentanolides with thiosemicarbazide, followed by treatment with alkali, resulted in formation of 2-(5-mercapto-1,2,4-triazol-3-ylmethyl)-4-pentanolides.

  DOI：

  10.1023/a:1016338226670

文献信息

• COMPOUNDS FOR THE TREATMENT OF CNS DISORDERS
  申请人：Fuchs Klaus

  公开号：US20120115863A1

  公开（公告）日：2012-05-10

  The invention relates to novel cycloalkyl- or cycloalkenyl-substituted pyrazolopyrimidinones of formula (I), wherein Ā is selected from the group A 1 consisting of a C 3 -C 8 -cycloalkyl group or a C 4 -C 8 -cycloalkenyl group, whereby the members of C 3 -C 8 -cycloalkyl group being selected from the group of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptanyl and cyclooctanyl; and the members of the C 4 -C 8 -cycloalkenyl group, being selected from cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, cyclopentadienyl, cyclohexadienyl, cycloheptadienyl, cyclooctadienyl, cycloheptatrienyl, cyclooctathenyl, cyclooctatetraenyl. The new compounds shall be used for the manufacture of medicaments, in particular medicaments for improving perception, concentration, learning and/or memory in patients in need thereof. Chemically, the compounds are characterised as pyrazolopyrimidinones with a cycloalkyl-moiety directly bound to the 1 position of the pyrazolopyrimidinone and a second substituent in the 6 position which is bound via an optionally substituted methylene-bridge. Further aspects of the present invention refer to a process for the manufacture of the compounds and their use for producing medicaments.

  该发明涉及具有以下结构的新型环烷基或环烯基取代的吡唑吡咪啉酮化合物（I），其中Ā选自A1组中的C3-C8环烷基或C4-C8环烯基，其中C3-C8环烷基组成员选自环丙基、环丁基、环戊基、环己基、环庚基和环辛基；而C4-C8环烯基组成员选自环丁烯基、环戊烯基、环己烯基、环庚烯基、环辛烯基、环戊二烯基、环己二烯基、环庚二烯基、环辛二烯基、环庚三烯基、环辛烷基、环辛四烯基。这些新化合物可用于制造药物，特别是用于改善患者感知、注意力、学习和/或记忆的药物。从化学上讲，这些化合物被描述为在吡唑吡咪啉酮的1位上直接连接有环烷基基团，并且在6位上通过一个可选取代的亚甲基桥连接有第二取代基。该发明的进一步方面涉及一种制造这些化合物的方法以及它们用于生产药物的用途。
• Continuous-Flow Preparation of γ-Butyrolactone Scaffolds from Renewable Fumaric and Itaconic Acids under Photosensitized Conditions
  作者：Romaric Gérardy、Marc Winter、Clemens R. Horn、Alessandra Vizza、Kristof Van Hecke、Jean-Christophe M. Monbaliu

  DOI：10.1021/acs.oprd.7b00314

  日期：2017.12.15

  lab-scale mesofluidic reactor connected with an in-line NMR spectrometer for real-time reaction monitoring. Substituted γ-butyrolactones, including spiro derivatives with unique structural features, were obtained with quantitative conversion of the starting materials and in 47–76% isolated yields. The model photoaddition of isopropanol to fumaric acid was next successfully transposed in a pilot-scale continuous-flow

  本文所述的方法和结果涉及在玻璃微流体反应器和中流体反应器中在可缩放的连续流条件下向可再生平台富马酸和衣康酸中光敏加成各种醇。酒精既用作试剂又用作溶剂，因此有助于减少环境足迹。在微流体条件下评估温度，光强度，光敏剂的性质和数量等工艺参数，然后将其转移到实验室规模的中流体反应器中，该反应器与在线NMR光谱仪连接以进行实时反应监控。取代后的γ-丁内酯（包括具有独特结构特征的螺衍生物）是通过原料的定量转化获得的，分离产率为47-76％。
• 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。
• Fittig; Thron, Justus Liebigs Annalen der Chemie, 1899, vol. 304, p. 281
  作者：Fittig、Thron

  DOI：——

  日期：——
• Fittig; Burwell, Justus Liebigs Annalen der Chemie, 1899, vol. 304, p. 259
  作者：Fittig、Burwell

  DOI：——

  日期：——