dibenzyl 2-hydroxysuccinate | 56977-10-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: dibenzyl 2-hydroxysuccinate
• 英文别名: dibenzyl malate；Dibenzyl 2-hydroxybutanedioate
• CAS: 56977-10-7
• 化学式: C₁₈H₁₈O₅
• 分子量: 314.338
• InChiKey: RWMHFANJOASIHT-UHFFFAOYSA-N

物化性质

• 沸点：
  474.6±35.0 °C(Predicted)
• 密度：
  1.238±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dibenzyl 2-hydroxysuccinate 在 2,6-二甲基吡啶 、 N-甲基哌啶 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 41.75h， 生成 2-[(R)-1-Benzyl-5-tert-butoxycarbonyl-pyrrolidin-(2Z)-ylidene]-succinic acid dibenzyl ester
  参考文献：
  名称：

  Enantiospecific Synthesis of Natural (−)-Cocaine and Unnatural (+)-Cocaine from d- and l-Glutamic Acid

  摘要：

  Natural (-)-cocaine and unnatural (+)-cocaine have been synthesized enantiospecifically from D- and L-glutamic acid, respectively. The axial-equatorial substitutents were introduced by a stereo- and regiospecific dipolar cycloaddition to the corresponding (LR,5S)- and (1S,5R)-N-BOC-nortropenes with (ethoxycarbonyl)formonitrile N-oxide. A sequence of subsequent stereochemically controlled transformations converted the fused isoxazoline to the requisite P-hydroxy ester. Synthesis of the key intermediate N-BOC-nortropenes involved construction of the 8-azabicyclo[3.2.1]octane framework by Dieckmann condensation of cis-5-substituted D-and L-proline esters. For comparison, (1R,SS)-N-BOC-nortropene also was derived by degradation from natural cocaine. The cis-5-substituted D-and L-proline esters were obtained by sulfide contraction and subsequent catalytic hydrogenation to induce stereospecifically the C-5 stereochemistry from D-and L-thiopyroglutamate, which in turn were prepared from D-and L-glutamic acids, respectively.

  DOI：

  10.1021/jo980153t
• 作为产物：
  描述：

  苹果酸 、 溴甲苯 在 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以66%的产率得到dibenzyl 2-hydroxysuccinate
  参考文献：
  名称：

  二醇的选择性单酰化和二不对称Desymmetrization观-Tartrates使用2-吡啶基酯作为酰化剂和金属羧酸盐作为催化剂

  摘要：

  用2-吡啶基苯甲酸酯作为酰化剂和Zn（OAc）2作为催化剂，1,2-二醇，1,3-二醇和邻苯二酚被选择性地单酰化。此外，首次实现了酒石酸内消旋酒石酸酯的高对映选择性去对称化，这是通过在CH 3 CN中使用2-吡啶基酯和NiBr 2 / AgOPiv / Ph-BOX或在EtOAc催化剂体系中使用CuCl 2 / AgOPiv / Ph-BOX来实现的（对等）到96％ee）。后者的催化剂体系，也是有效的苄动力学拆分DL -酒石酸盐。

  DOI：

  10.1021/acs.joc.9b00827

文献信息

• THERMOCLEAVABLE FRICTION MODIFIERS AND METHODS THEREOF
  申请人：Rutgers, The State University of New Jersey

  公开号：US20180037840A1

  公开（公告）日：2018-02-08

  Certain embodiments of the invention provide a lubricating oil composition comprising a lubricating oil base stock and a compound of formula (I): or a salt thereof, wherein R 1 , R 2 , R 3 and R 4 have any of the values defined in the specification, as well as methods of use thereof.

  该发明的某些实施例提供一种润滑油组合物，包括润滑油基础油和化合物的公式(I)：或其盐，其中R1、R2、R3和R4具有规范中定义的任何值，以及其使用方法。
• Hydrogenolysis of Benzyl Esters with Palladiumon-Carbon Catalysts
  作者：Harold L. Smith、Earle S. Brown、J. Doyle Smith、John Andrako

  DOI：10.1002/jps.2600540909

  日期：1965.9

  stereospecific sites on palladized charcoal hydrogenation catalysts have been made. The rates of hydrogenation of the benzyl esters of (+), (−), (±), and meso -tartaric acids, (±) malic acid, d -, l -, and dl -aspartic acids were measured. The rates were observed to be identical for the benzyl esters of the tartaric acids and the malic acid, indicating the possibility that these five substrates can utilize the

  进行了进一步的研究以证明在钯制木炭加氢催化剂上可能存在底物和立体特异性位点。测定了（+），（-），（±）和内消旋酒石酸，（±）苹果酸，d-，l-和dl-天冬氨酸的苄酯的氢化率。观察到酒石酸和苹果酸的苄基酯的速率相同，表明这五个底物可以利用相同的催化位点进行脱苄基作用的可能性。假定一个羟基和两个羰基苄氧基参与了催化剂-底物的复合物。当彼此比较时，二苄基天冬氨酸以相同的速率进行脱苄基作用。当与这些其他物质的速率相比时，发现琥珀酸二苄酯的氢解速率显着不同。不含羟基或氨基的琥珀酸二苄酯不会被期望利用与酒石酸，苹果酸和天冬氨酸的二苄酯相同的位点。
• Hydroxy-oligocarboxylic esters: effects on nerve and use for cutaneous and mucocutaneous organs or sites
  申请人：Yu J. Ruey

  公开号：US20070093551A1

  公开（公告）日：2007-04-26

  A composition and method for producing a beneficial effect on a subject's nerve associated with at least one of a cosmetic condition, a dermatological indication and a dental indication and another condition. The composition comprises a hydroxy-oligocarboxylic ester and is formulated for topical administration of the product to a subject to produce the beneficial effect. The method includes topically applying to the subject in a region where the beneficial effect is desired a hydroxy-oligocarboxylic ester in an amount effective to produce the beneficial effect.

  一种用于产生对与至少一种美容状况、皮肤学指示和牙科指示以及另一种状况相关的主体神经有益作用的组合物和方法。该组合物包含羟基寡聚羧酸酯，并且配制为局部给药形式，以产生有益作用。该方法包括在所需产生有益作用的区域局部施用羟基寡聚羧酸酯，其用量有效地产生有益作用。
• [EN] COMBINATIONS COMPRISING BIPHENYL DERIVATIVES FOR USE IN THE TREATMENT OF HCV<br/>[FR] ASSOCIATIONS COMPRENANT DES DÉRIVÉS DE BIPHÉNYLE DESTINÉES À ÊTRE UTILISÉES POUR LE TRAITEMENT DU VIRUS DE L'HÉPATITE C
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2015009744A1

  公开（公告）日：2015-01-22

  The present disclosure is generally directed to antiviral compounds, and more specifically directed to combinations of compounds which can inhibit the function of the NS5A protein encoded by Hepatitis C virus (HCV), compositions comprising such combinations, and methods for inhibiting the function of the NS5A protein.

  本公开涉及抗病毒化合物，更具体地涉及能够抑制由丙型肝炎病毒（HCV）编码的NS5A蛋白质的功能的化合物组合、包含这样的组合物的组合物以及抑制NS5A蛋白质功能的方法。
• Malic acid diester surfactants
  申请人：——

  公开号：US20020103280A1

  公开（公告）日：2002-08-01

  This invention provides water-based compositions, particularly coating, ink, fountain solution, adhesive and agricultural compositions, manifesting reduced equilibrium and dynamic surface tension by the incorporation of a surface tension reducing amount of certain malate diester compounds of the structure 1 where R 1 and R 2 are C3 to C6 alkyl groups.

  本发明提供了水性组合物，特别是涂料、油墨、喷泉溶液、粘合剂和农业组合物，通过加入一定量的某些苹果酸二酯化合物来表现出降低的平衡和动态表面张力，其中该化合物的结构为1，其中R1和R2为C3到C6的烷基。