5-benzoylpyrrolidin-2-one | 111556-29-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-benzoylpyrrolidin-2-one
• 英文别名: (+/-)-5-oxopyrrolidin-2-yl phenyl ketone；5-benzoyl-2-pyrrolidinone；5-benzoyl-2-pyrrolidone
• CAS: 111556-29-7
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: LBKGPOUNLPXMRF-UHFFFAOYSA-N

物化性质

• 熔点：
  155-156 °C(Solv: pentane (109-66-0))
• 沸点：
  413.2±38.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-benzoylpyrrolidin-2-one 在 sodium hydroxide 、 lithium aluminium tetrahydride 作用下， 生成 <(S)-pyrrolidin-2-yl>benzyl alcohol
  参考文献：
  名称：

  Ookawa, Atsuhiro; Soai, Kenso, Journal of the Chemical Society. Perkin transactions I, 1987, p. 1465 - 1472

  摘要：

  DOI：
• 作为产物：
  描述：

  炔丙基脲 在 四(三苯基膦)钯 copper(l) iodide 、 ammonium cerium(IV) nitrate 、 2,2,2-三氟乙醇 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 二乙胺 、 三乙胺 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 2.5h， 生成 5-benzoylpyrrolidin-2-one
  参考文献：
  名称：

  Expeditious Approach to 5-Aroyl-pyrrolidinones by a Novel PIFA-Mediated Alkyne Amidation Reaction

  摘要：

  A novel metal-free approach to the alkyne amidation reaction is presented. The oxidation of properly substituted amides by the hypervalent iodine reagent PIFA provides the generation of a nitreniurn ion that can react intramolecularly with a triple bond, leading to the construction of the title compounds.

  DOI：

  10.1021/ol0510623

文献信息

• THERAPEUTIC AGENT FOR DIABETES
  申请人：Japan Tobacco Inc.

  公开号：EP0885869A1

  公开（公告）日：1998-12-23

  A therapeutic agent for diabetes, which comprises a compound of the formula [I] wherein Xis a group of the formula wherein R4 and R5 are the same or different and each is a hydrogen atom, an optionally substituted alkyl having 1 to 5 carbon atoms and the like, and R6 is a hydrogen atom or an amino-protecting group; R1 is an optionally substituted alkyl having 1 to 5 carbon atoms, an optionally substituted alkenyl having 2 to 6 carbon atoms and the like, R2 is a hydrogen atom, an optionally substituted alkyl having 1 to 5 carbon atoms and the like, R2' is a hydrogen atom, and R3 is an optionally substituted alkyl having 1 to 5 carbon atoms and the like, a prodrug thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof and a solvate thereof. The compound of the present invention shows superior blood sugar decreasing action on the state of hyperglycemia, but does not affect the blood sugar when it is in the normal range or in the hypoglycemic state, which means that it is free of serious side effects such as hypoglycemia. Therefore, the compound of the present invention is useful as a therapeutic drug for diabetes and also useful as a preventive of the chronic complications of diabetes.

  用于治疗糖尿病的疗法剂，包括公式[I]的化合物 其中 X是公式的组 其中R4和R5相同或不同，每个都是氢原子，可选地取代的具有1至5个碳原子的烷基等等，R6是氢原子或氨基保护基团；R1是具有1至5个碳原子的可选取代烷基，具有2至6个碳原子的可选取代烯基等等，R2是氢原子，具有1至5个碳原子的可选取代烷基等等，R2'是氢原子，R3是具有1至5个碳原子的可选取代烷基等等，其前药，药用可接受盐，水合物和溶剂化物。 本发明的化合物在血糖升高状态下表现出优越的降血糖作用，但在正常范围或低血糖状态下不影响血糖，这意味着它没有低血糖等严重副作用。因此，本发明的化合物作为治疗糖尿病的药物很有用，也用作预防糖尿病慢性并发症。
• 2-Pyrrolidine methanol derivatives utilizable as medicaments
  申请人：Pharmindustrie

  公开号：US04248884A1

  公开（公告）日：1981-02-03

  The compounds of the formula: ##STR1## in which X is a hydrogen or halogen atom or an alkoxy group having 1 to 4 carbon atoms, an alkyl or cycloalkyl group having 1 to 8 carbon atoms, and R represents a hydrogen atom, alkyl group having 1 to 4 carbon atoms, or an aralkyl or hydroxyalkyl group in which the alkyl chain has 1 to 4 carbon atoms are disclosed together with processes for their preparation and medicaments containing the compounds. These compounds are hypolipemiants. In addition, some of them are psychostimulants.

  该公式化合物：##STR1##其中X是氢原子或卤素原子或具有1至4个碳原子的烷氧基团，具有1至8个碳原子的烷基或环烷基团，R代表氢原子，具有1至4个碳原子的烷基团，或者烷基链具有1至4个碳原子的芳基烷基或羟基烷基团，还公开了它们的制备过程和含有这些化合物的药物。这些化合物是降脂药。此外，其中一些是精神刺激剂。
• Studies on Pyrrolidinones. An Improved Synthesis of Pyroglutamoyl Chloride
  作者：Benoit Rigo、Samira El Ghammarti、Philippe Gautret、Daniel Couturier

  DOI：10.1080/00397919408010572

  日期：1994.10

  Abstract The reaction of trimethylsilyl pyroglutamate with oxalyl chloride at room temperature easily yields pyroglutamoyl chloride. This unstable compound, obtained with difficulty by other methods, is suitable for the preparation of pyroglutamic esters and amides.

  摘要 焦谷氨酸三甲基甲硅烷基酯与草酰氯在室温下反应容易生成焦谷氨酰氯。这种通过其他方法难以获得的不稳定化合物适用于制备焦谷氨酸酯和酰胺。
• Tellitu, Imanol; Serna, Sonia; Dominguez, Esther, ARKIVOC, 2010, vol. 2010, # 3, p. 7 - 14
  作者：Tellitu, Imanol、Serna, Sonia、Dominguez, Esther

  DOI：——

  日期：——
• OOKAWA, ATSUHIRO;SOAI, KENSO, J. CHEM. SOC. PERKIN TRANS.,(1987) N 7, 1465-1471
  作者：OOKAWA, ATSUHIRO、SOAI, KENSO

  DOI：——

  日期：——