(3R,4R)-1-phenyl-3,4-dihydroxy-2,5-dioxopyrrolidine | 69669-21-2

• 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)-1-phenyl-3,4-dihydroxy-2,5-dioxopyrrolidine
• 英文别名: N-phenyltartrimide；(3R)-3r,4t-dihydroxy-1-phenyl-pyrrolidine-2,5-dione；(3R)-3r,4t-Dihydroxy-1-phenyl-pyrrolidin-2,5-dion；(3R,4R)-3,4-dihydroxy-1-phenylpyrrolidine-2,5-dione
• CAS: 69669-21-2
• 化学式: C₁₀H₉NO₄
• 分子量: 207.186
• InChiKey: VVCQJDHMWMRSEC-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  77.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4R)-1-phenyl-3,4-dihydroxy-2,5-dioxopyrrolidine 在 lithium aluminium tetrahydride 、 silica gel 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 (3R,4R)-N3,N4-bis[3,5-di-t-butylsalicylidene]-1-phenyl-3,4-diaminopyrrolidine
  参考文献：
  名称：

  The synthesis of tetradentate salens derived from (3R,4R)-N-substituted-3,4-diaminopyrrolidines and their application in the enantioselective trimethylsilylcyanation of aromatic aldehydes

  摘要：

  The in situ formed Ti(IV) complexes of pyrrolidine-based chiral salen ligands derived from natural L-tartaric acid were evaluated as catalysts in the enantioselective trimethylsilylcyanation of aromatic aldehydes. The different activity and selectivity of the catalysts in the formation of the products were found to be dependent on the N-substituent of the pyrrolidine. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.01.015
• 作为产物：
  描述：

  L-酒石酸 、 苯胺 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 以87%的产率得到(3R,4R)-1-phenyl-3,4-dihydroxy-2,5-dioxopyrrolidine
  参考文献：
  名称：

  3，4-二羟基吡咯烷-2，5-二酮和3，5-二羟基苯甲酸衍生物的合成以及对碳酸酐酶Ⅰ和Ⅱ的抑制作用的评价。

  摘要：

  通过酯酶试验研究了两种3,4-二羟基吡咯烷-2,5-二酮和3,5-二羟基苯甲酸衍生物对两种人胞质碳酸酐酶（hCA，EC 4.2.1.1）同工酶I和II的抑制作用。 ，以乙酸4-硝基苯酯（4-NPA）为底物。对于hCA I，化合物10-13的KI值分别在112.7-441.5μM范围内；对hCA II，化合物10-13的KI值分别在3.5-10.76μM范围内。这些含羟基的化合物通常是竞争性抑制剂。此处研究的某些含羟基的化合物显示出有效的hCA II抑制作用，与​​临床使用的磺酰胺乙酰唑酰胺在相同范围内，并且可以用作产生酶抑制剂的先导，这些酶抑制剂可能靶向尚未与它们相互作用的其他CA亚型。这样的代理商。

  DOI：

  10.3109/14756366.2014.983917
• 作为试剂：
  描述：

  2-戊醇 在 硫酸 、 (3R,4R)-1-phenyl-3,4-dihydroxy-2,5-dioxopyrrolidine 作用下， 生成 (R)-2-pentanol
  参考文献：
  名称：

  144.通过与酒石酸的酯拆分非活性醇

  摘要：

  DOI：

  10.1039/jr9390000638

文献信息

• Tartaric acid and its O-acyl derivatives. Part 8. Direct synthesis of novel N-substituted mono- and diacyltartrimides: unusual reaction course
  作者：Paweł Ruśkowski、Ludwik Synoradzki、Marek Włostowski

  DOI：10.3998/ark.5550190.0012.910

  日期：——

  Unexpected hydrolysis of diacyl tartaric acids during their reaction with primary amines yielded new monoacyl tartrimides.

  二酰基酒石酸在与伯胺反应期间意外水解，产生新的单酰基酒石酰亚胺。
• Asymmetric hydrogenations catalysed by diphosphinite rhodium complexes derived from natural tartaric acid
  作者：Jean Bourson、Laureano Oliveros

  DOI：10.1016/s0022-328x(00)89118-4

  日期：1982.4

  Two chiral diphosphinites, derived from natural tartaric acid, have been prepared and used as ligands for the preparation of two asymmetric hydrogenation catalysts, which were isolated in a crystalline state. After several weeks storage, these catlysts are still effective in the asymmetric hydrogenation of α-acetamido- and α-benzamido-cinnamic acid, citraconic acid, 2-phenyl-1-butene. In the hydrogenation

  已经制备了两种衍生自天然酒石酸的手性二亚膦酸酯，并将其用作制备两种不对称氢化催化剂的配体，所述两种不对称氢化催化剂以结晶状态分离。储存数周后，这些催化剂在α-乙酰氨基-和α-苯甲酰胺基肉桂酸，柠康酸，2-苯基-1-丁烯的不对称氢化中仍然有效。在氨基酸前体的氢化中，光学产率为14-44％。从给定的基底开始，每次两个对映体可通过我们的两种催化剂，它们是这样彼此互补的一个的适当选择而获得。考虑了氢化中各种因素对光学产率的影响。
• Molecular tectonics: design of enantiomerically pure helical tubular crystals with controlled channel size and orientation
  作者：Mei-Jin Lin、Abdelaziz Jouaiti、Philippe Grosshans、Nathalie Kyritsakas、Mir Wais Hosseini

  DOI：10.1039/c1cc12110c

  日期：——

  The combination of four enantiomerically pure organic tectons composed of a rigid chiral backbone bearing two terminal pyridyl coordinating sites with ZnSiF6 behaving as an infinite pillar leads to the formation of tubular 2-D enantiomerically pure helical channels with controlled size and orientation.

  四种对映体纯度极高的有机结构体由带有两个末端吡啶配位位点的刚性手性骨架组成，而 ZnSiF6 具有无限支柱的作用，两者的结合形成了尺寸和方向可控的管状二维对映体纯度螺旋通道。
• Antiviral agents. 2. Structure-activity relations of compounds related to 1-adamantanamine
  作者：Paul E. Aldrich、Edward C. Hermann、Walter E. Meier、Marvin Paulshock、William W. Prichard、Jack Austin Synder、John C. Watts

  DOI：10.1021/jm00288a019

  日期：1971.6
• The synthesis of tetradentate salens derived from (3R,4R)-N-substituted-3,4-diaminopyrrolidines and their application in the enantioselective trimethylsilylcyanation of aromatic aldehydes
  作者：M. Elisa Silva Serra、Dina Murtinho、Albertino Goth

  DOI：10.1016/j.tetasy.2013.01.015

  日期：2013.3

  The in situ formed Ti(IV) complexes of pyrrolidine-based chiral salen ligands derived from natural L-tartaric acid were evaluated as catalysts in the enantioselective trimethylsilylcyanation of aromatic aldehydes. The different activity and selectivity of the catalysts in the formation of the products were found to be dependent on the N-substituent of the pyrrolidine. (C) 2013 Elsevier Ltd. All rights reserved.