(3R,4R)-3,4-diacetoxy-1-methylpyrrolidine-2,5-dione | 136137-81-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3R,4R)-3,4-diacetoxy-1-methylpyrrolidine-2,5-dione
• 英文别名: [(3R,4R)-4-acetyloxy-1-methyl-2,5-dioxopyrrolidin-3-yl] acetate
• CAS: 136137-81-0
• 化学式: C₉H₁₁NO₆
• 分子量: 229.189
• InChiKey: UEMZXWXITNRCAQ-RNFRBKRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  90
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3R,4R)-3,4-diacetoxy-1-methylpyrrolidine-2,5-dione 在 sodium tetrahydroborate 、 三氟甲磺酸三甲基硅酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.37h， 生成 (3R,4S,5R)-4-(acetyloxy)-5-allyl-1-methyl-2-oxopyrrolidin-3-yl acetate
  参考文献：
  名称：

  O-(2-Oxopyrrolidin-5-yl)trichloroacetimidates 作为酰胺烷基化剂 - (+)-Lentiginosine 的合成

  摘要：

  N-α-羟基烷基酰胺 6a,b，容易从 L-酒石酸盐获得，与三氯乙腈一起提供 O-(2-氧代吡咯烷-5-基)三氯乙酰亚胺酯 3a,b。使用烯丙基-三甲基硅烷和富电子苯衍生物作为 C-亲核试剂对 3a,b 进行 α-酰胺基烷基化研究，得到 5-烯丙基-和 5-芳基-2-吡咯烷酮 2a,b、7a、b 和 8-10。目标化合物 (+)-1 及其差向异构体 15 分别由 1,5-二烯丙基-2-吡咯烷酮 2b 和 7b 通过闭环复分解、酰胺基团还原和 CC-双键氢化反应得到。(© Wiley-VCH Verlag GmbH & Co KGaA, 69451 Weinheim, Germany, 2002)

  DOI：

  10.1002/1099-0690(200212)2002:24<4137::aid-ejoc4137>3.0.co;2-x
• 作为产物：
  描述：

  ammonium (2R,3R)-2,3-diacetoxy-3-carbamoylpropionate 在 吡啶 、 磺酰氯 、 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.17h， 生成 (3R,4R)-3,4-diacetoxy-1-methylpyrrolidine-2,5-dione
  参考文献：
  名称：

  Gabriel 路线的酒石酸酰胺

  摘要：

  旋光性(3R,4R)-3,4-二乙酰氧基吡咯烷-2,5-二酮是由L-酒石酸通过(2R,3R)-2,3-二乙酰氧基-3-氨基甲酰基丙酸的铵盐闭环制备的与亚硫酰氯。机理考虑表明，环闭合通过两种竞争途径进行：中间体酰氯的直接环闭合或通过乙烯酮中间体的平行途径。环状产物分别通过水解和与合适的烷基胺反应进一步转化为旋光酒石单酰胺和酒石双酰胺。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

  DOI：

  10.1002/ejoc.200700198

文献信息

• Chiral cyclic imides with c2-symmetry. Novel reagents for the synthesis of optically pure lactones containing three contiguous tertiary centers
  作者：Hidemi Yoda、Koji Shirakawa、Kunihiko Takabe

  DOI：10.1016/s0040-4039(00)92719-9

  日期：1991.7

  Asymmetric reactions employing C2-symmetrical imides readily prepared from L-tartaric acid with Grignard reagents and sodium borohydride afforded a separable mixture of two hydroxyamides with high diastereoselectivity. Products were lactonized respectively to provide optically pure γ- alkylated lactones with contiguous tertiary carbon centers. The reaction mechanisms in asymmetric induction were also

  使用由L-酒石酸与Grignard试剂和氢硼化钠轻松制备的C 2-对称酰亚胺进行的不对称反应提供了具有高非对映选择性的两种羟酰胺的可分离混合物。将产物分别内酯化以提供具有连续的叔碳中心的光学纯的γ-烷基化内酯。还讨论了不对称诱导中的反应机理。
• Dicaffeoyl- or digalloyl pyrrolidine and furan derivatives as HIV integrase inhibitors
  作者：Dong Jin Hwang、Sun Nam Kim、Jung Hoon Choi、Yong Sup Lee

  DOI：10.1016/s0968-0896(01)00013-x

  日期：2001.6

  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.
• US5571909A
  申请人：——

  公开号：US5571909A

  公开（公告）日：1996-11-05