(E)-benzylidenesuccinic anhydride | 125702-11-6

• 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: (E)-benzylidenesuccinic anhydride
• 英文别名: (E)-3-benzylidene-dihydrofuran-2,5-dione；(E)-3-benzylidenedihydrofuran-2,5-dione；(E)-2-benzylidenesuccinic anhydride；benzylidene-succinic acid anhydride；[(E)-benzylidene-succinic acid-anhydride；[(E)-Benzyliden-bernsteinsaeure-anhydrid；(3E)-3-benzylideneoxolane-2,5-dione
• CAS: 125702-11-6
• 化学式: C₁₁H₈O₃
• 分子量: 188.183
• InChiKey: WHRPHGQMEZWMNF-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-benzylidenesuccinic anhydride 在 palladium on activated charcoal N-甲基吗啉 、 sodium hydroxide 、 氢气 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 tert-butyl (2S)-2-[[(2S,3S)-2-[[2-benzyl-4-(hydroxyamino)-4-oxobutanoyl]amino]-3-methylpentanoyl]amino]-4-methylpentanoate
  参考文献：
  名称：

  N- [3-[（羟氨基）羰基] -1-氧代-2（R）-苄基丙基] -L-异亮氨酰-L-亮氨酸的合成和止痛作用，它是多种神经降压素/ neuromedin N降解酶的新型有效抑制剂。

  摘要：

  N- [3-[（羟氨基）羰基] -1-氧代-2（R）-苄基丙基] -L-异亮氨酰-L-亮氨酸（JMV-390-1，6a）的合成，基于描述了神经降压素（NT）和神经调节素N（NN）共有的C端序列。该化合物在体外具有主要NT / NN降解酶（例如内肽酶24.16，内肽酶24.15，内肽酶24.11和亮氨酸氨基肽酶（IV-S型）的完全抑制剂）的纳摩尔浓度范围（IC50为30至60 nM）。 。发现化合物6a增加了用钾去极化的小鼠下丘脑切片中NT和NN的内源性恢复。在通常用于选择镇痛药的各种试验中，例如热板试验，甩尾试验，乙酸诱导的扭体试验，在小鼠的脑室内（icv）注射时，化合物6a被证明是有效的。所观察到的镇痛作用被阿片类药物纳曲酮完全（热板试验）或大部分（甩尾试验）逆转。此外，发现icv注射化合物6a（10微克/小鼠）可显着增强NT或NN的低温效应。

  DOI：

  10.1021/jm00062a009
• 作为产物：
  描述：

  苄基马来酸 在 sodium hydroxide 作用下， 生成 (E)-benzylidenesuccinic anhydride
  参考文献：
  名称：

  Fittig; Brooke, Justus Liebigs Annalen der Chemie, 1899, vol. 305, p. 21

  摘要：

  DOI：

文献信息

• Efficient cyclodehydration of dicarboxylic acids with oxalyl chloride
  作者：Grigory Kantin、Evgeny Chupakhin、Dmitry Dar'in、Mikhail Krasavin

  DOI：10.1016/j.tetlet.2017.06.089

  日期：2017.8

  Literature examples illustrating the use of oxalyl chloride to prepare dicarboxylic acid anhydrides are surprisingly limited. At the same time, we have discovered a method involving the use of this readily available reagent which allowed the preparation of novel cyclic anhydrides where other, more conventional, methods had failed. Herein, we demonstrate that the method is applicable to a wide diversity

  令人惊讶地限制了说明使用草酰氯制备二羧酸酐的文献实例。同时，我们发现了一种方法，该方法涉及使用这种现成的试剂，该试剂可在其他更常规的方法失败的情况下制备新型环酐。在本文中，我们证明了该方法适用于多种底物，无需色谱纯化即可提供良好的环酸酐产量，并且在需要二羧酸环脱水的任何时候都可以将其视为合成工具的选择。
• Modular 1,1′-Ferrocenediyl-cored <i>P</i> -Stereogenic Diphosphines: ′′JDayPhos′′ Series and its Use in Rhodium(I)-Catalyzed Hydrogenation
  作者：Gašper Poklukar、Michel Stephan、Barbara Mohar

  DOI：10.1002/adsc.201800255

  日期：2018.7.4

  A novel ferrocene‐based P‐stereogenic diphospine ligand series dubbed JDayPhos was developed, which rhodium(I) complexes of some of its members exhibited excellent enantioselectivity (up to >99% ee) and high activity in asymmetric hydrogenation of β‐unsubstituted or ‐substituted itaconates and α‐methylene‐γ‐oxo‐carboxylates.

  开发了一种新型的基于二茂铁的P-立体异构二膦配体系列JDayPhos，该化合物的一些成员的铑（I）配合物表现出出色的对映选择性（高达> 99％ee），并且在β-未取代或-β的不对称氢化中表现出高活性。取代的衣康酸酯和α-亚甲基-γ-氧代羧酸酯。
• Succinic acid compounds
  申请人：Kissei Pharmaceutical Co., Ltd.

  公开号：US05202335A1

  公开（公告）日：1993-04-13

  Succinic acid compounds of the formula: ##STR1## wherein A represents a heterocyclic group, a 3 to 8-membered cycloalkyl group or a phenyl group which may have one or more substituents selected from the group of a halogen atom, a lower alkyl group having 1 to 6 carbon atoms and a lower alkoxy group having 1 to 6 carbon atoms; B represents a bicyclic amino group which may have 1 or 2 unsaturated bonds, with the proviso that B bonds to the carbon atom of the carbonyl group at the nitrogen atom; R represents a hydrogen atom or combines each other to form a chemical bond; R.sup.1 represents a hydrogen atom, a lower alkyl group having 1 to 6 carbon atoms or an aralkyl group having 7 to 10 carbon atoms; when there is an asymmetric carbon atom, enantiomers thereof and racemic mixtures thereof; when there are geometrical isomers, each geometrical isomer, E-isomers thereof, Z-isomers thereof, cis-isomers thereof and trans-isomers thereof; and pharmaceutically acceptable salts thereof, enhance insulin secretion and possess a hypoglycemic activity, and are thus useful for the treatment of diabetes.

  Succinic acid compounds of the formula: ##STR1## wherein A represents a heterocyclic group, a 3 to 8-membered cycloalkyl group or a phenyl group which may have one or more substituents selected from the group of a halogen atom, a lower alkyl group having 1 to 6 carbon atoms and a lower alkoxy group having 1 to 6 carbon atoms; B represents a bicyclic amino group which may have 1 or 2 unsaturated bonds, with the proviso that B bonds to the carbon atom of the carbonyl group at the nitrogen atom; R represents a hydrogen atom or combines each other to form a chemical bond; R.sup.1 represents a hydrogen atom, a lower alkyl group having 1 to 6 carbon atoms or an aralkyl group having 7 to 10 carbon atoms; when there is an asymmetric carbon atom, enantiomers thereof and racemic mixtures thereof; when there are geometrical isomers, each geometrical isomer, E-isomers thereof, Z-isomers thereof, cis-isomers thereof and trans-isomers thereof; and pharmaceutically acceptable salts thereof, enhance insulin secretion and possess a hypoglycemic activity, and are thus useful for the treatment of diabetes.
• Novel Ylidic Phosphoryl Compounds from Halogenated Furan-2,5-Diones with Trivalent Phosphorus Esters: Application of this Approach to New Trisphosphonates Containing a Geminal Bisphosphonate Unit
  作者：D. Vaughan Griffiths、David M. Benoit、Yuen-Ki Cheong、Philip Duncanson、Xiao Han

  DOI：10.1080/10426507.2014.905570

  日期：2014.8.3

  Abstract The reactions of trivalent phosphorus esters, including trialkyl phosphites, dialkyl phosphonites, and alkyl phosphinites, with 3-halo- and 3,4-dihalo-furan-2,5-diones has been shown to lead to the formation of novel phosphorus ylides possessing additional phosphoryl-containing groups. For the reaction of 3,4-dihalo-furan-2,5-diones with trialkyl phosphites, the products are trialkoxyphosphonium

  摘要 三价磷酯，包括三烷基亚磷酸酯、二烷基亚膦酸酯和烷基亚膦酸酯，与 3-卤-和 3,4-二卤-呋喃-2,5-二酮的反应已被证明会导致形成新的磷叶立德。拥有额外的含磷酰基基团。对于 3,4-二卤代-呋喃-2,5-二酮与亚磷酸三烷基酯的反应，产物是三烷氧基鏻叶立德，含有相邻的双膦酸单元。这些可用于为新型 2,3,3-三(二烷氧基磷酰基)-取代的丙酸酯提供方便的途径，该丙酸酯可水解得到相应的新型三膦酸一元羧酸。图形概要
• Preparation of Optically Active Succinic Acid Derivatives. I. Optical Resolution of 2-Benzyl-3-(cis-hexahydroisoindolin-2-ylcarbonyl)propionic Acid.
  作者：Toshiaki YAMAGUCHI、Takashi YANAGI、Hiroshi HOKARI、Yuko MUKAIYAMA、Tetsuhide KAMIJO、Iwao YAMAMOTO

  DOI：10.1248/cpb.45.1518

  日期：——

  (+)-Monocalcium bis[(2S)-2-benzyl-3-(cis-hexahydroisoindolin-2-ylcarbonyl)propionate] dihydrate (KAD-1229, 1) is an optically active succinic acid calcium salt derivative with potent hypoglycemic effect. We investigated two optical resolution methods. 2-Benzyl-3-(cis-hexahydroisoindolin-2-ylcarbonyl)propionic acid 6 was esterified with (S)-N-benzyl mandelamide and the resulting diastereomeric esters were separated by column chromatography on silica gel to give 7 and 8 in 39.1% and 45.3% yields, respectively. The diastereomer 7 was hydrolyzed to give the optically active acid (-)-6. The absolute configuration of (-)-6 was established as S by comparison with an authentic sample. The alternative method was resolution using an optically active amine. Treatment of a solution of the racemic acid 6 with 0.65 eq of (R)-1-(1-naphthyl)ethylamine in ethanol gave the salt in 23.2% yield with an optical purity of 96.8% ee.

  (+)-双[(2S)-2-苄基-3-(顺式六氢异吲哚啉-2-基羰基)丙酸]单钙盐二水合物（KAD-1229，1）是一种光学活性琥珀酸钙盐衍生物，具有强效降血糖作用。我们研究了两种光学解析方法。2-Benzyl-3-(cis-hexahydroisoindolin-2-ylcarbonyl)propionic acid 6 与 (S)-N-benzyl mandelamide 发生酯化反应，得到的非对映异构酯经硅胶柱层析分离，得到 7 和 8，产率分别为 39.1%和 45.3%。非对映异构体 7 经水解后得到光学活性酸 (-)-6。通过与真实样品对比，确定 (-)-6 的绝对构型为 S。另一种方法是使用光学活性胺进行解析。用 0.65 eq (R)-1-(1-萘基)乙胺在乙醇中处理外消旋酸 6 的溶液，得到的盐的产率为 23.2%，光学纯度为 96.8%ee。