(3R,4R)-3,4-dihydroxypyrrolidine-2,5-dione | 18366-18-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (3R,4R)-3,4-dihydroxypyrrolidine-2,5-dione
• 英文别名: (2R,3R)-2,3-dihydroxysuccinimide；(3R,4R)-3,4-dihydroxysuccinimide；(3R)-trans-3,4-dihydroxy-pyrrolidine-2,5-dione；(3R)-trans-3,4-Dihydroxy-pyrrolidin-2,5-dion；(R,R)-Tartrimid
• CAS: 18366-18-2
• 化学式: C₄H₅NO₄
• 分子量: 131.088
• InChiKey: MPTQLFFTNNKMRP-JCYAYHJZSA-N

物化性质

• 沸点：
  441.5±45.0 °C(Predicted)
• 密度：
  1.827±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  叔丁基二甲基氯硅烷 、 (3R,4R)-3,4-dihydroxypyrrolidine-2,5-dione 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以74%的产率得到(3R,4R)-3,4-bis[(tert-butyldimethylsilyl)oxy]-2,5-pyrrolidindione
  参考文献：
  名称：

  Dicaffeoyl- or digalloyl pyrrolidine and furan derivatives as HIV integrase inhibitors

  摘要：

  Human immunodeficiency virus (HIV) integrase (IN) catalyzes the integration of HIV DNA copy into the host cell DNA. Such integration is essential for the production of progeny viruses, and therefore therapeutic agents that can inhibit this process should be effective anti-HIV agents. We have previously reported the inhibitory activity of dicaffeoylglucosides against HIV IN. In the present study, we have synthesized and tested dicaffeoyl or digalloyl compounds joined through a five-membered heterocyclic ring as HIV IN inhibitors to explore the SARs of this family of compounds. The starting heterocyclic diols were prepared from L-tartaric acid, diethyl L-tartarate or D-(+)-ribonic gamma -lactone. We found that the HIV IN inhibitory activities of dicaffeoyl derivatives were comparable to that of L-chicoric acid (IC50 = 24.9 muM). On the other hand, digalloyl derivatives were more potent than L-chicoric acid with IC50 Values of 4.7-15.6 muM. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00013-x
• 作为产物：
  描述：

  L-(+)-酒石酸二乙酯 在 乙醇 、 氨 作用下， 生成 (3R,4R)-3,4-dihydroxypyrrolidine-2,5-dione
  参考文献：
  名称：

  Badoche, Annales de Chimie (Cachan, France), 1943, vol. <11>18, p. 155

  摘要：

  DOI：

文献信息

• Synthesis of novel mucic acid 1,4-lactone methyl ester 3-O-ferulate related to an extractive component isolated from the peels of Citrus sudachi
  作者：Tetsuya Sengoku、Yusuke Murata、Hiromi Mitamura、Masaki Takahashi、Hidemi Yoda

  DOI：10.1016/j.tetlet.2011.11.066

  日期：2012.1

  Synthesis of a new type of mucic acid 1,4-lactone methyl ester 3-O-ferulate related to an extractive component isolated from Citrus sudachi, and its diastereomer has been achieved by employing stereodivergent dihydroxylation as a key step. The structures of the final products are fully characterized by spectroscopic methods and compared with that of the natural product. (C) 2011 Elsevier Ltd. All rights reserved.
• Polonski, Tadeusz, Journal of the Chemical Society. Perkin transactions I, 1988, p. 629 - 638
  作者：Polonski, Tadeusz

  DOI：——

  日期：——