(+/-)-2-(4-methoxybenzyl)succinic acid 1-methyl ester | 63151-86-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (+/-)-2-(4-methoxybenzyl)succinic acid 1-methyl ester
• 英文别名: (4-methoxy-benzyl)-succinic acid-1-methyl ester；(4-Methoxy-benzyl)-bernsteinsaeure-1-methylester；2-(4-methoxybenzyl)succinic acid 1-methyl ester；4-Methoxy-3-[(4-methoxyphenyl)methyl]-4-oxobutanoic acid
• CAS: 63151-86-0
• 化学式: C₁₃H₁₆O₅
• 分子量: 252.267
• InChiKey: HKMQODAJOVBRJT-UHFFFAOYSA-N

物化性质

• 熔点：
  35-37 °C
• 沸点：
  156 °C(Press: 1 Torr)
• 密度：
  1.196±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  (+/-)-2-(4-methoxybenzyl)succinic acid 1-methyl ester 在 三氟乙酸 、 三氟乙酸酐 作用下， 反应 8.0h， 以50%的产率得到methyl 6-methoxy-4-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate
  参考文献：
  名称：

  Kinetic resolution of 3-hydroxymethylbenzocycloalkanols by selective asymmetric hydrogen-transfer oxidation

  摘要：

  Kinetic resolution of 3-hydroxymethylbenzocycloalkanols was performed by selective asymmetric hydrogen-transfer oxidation using the Ru(II)-(S,S)-TsDPEN catalyst. Thus, several 3-hydroxymethyl-1-tetralols 7a-d afforded (1R,3R)-3-hydroxymethyl-1-tetralols (1R,3R)-7a-d and (S)-3-hydroxymethyl-1-tetralones (S)-9a-d, and 3-hydroxymethyl-1-indanol 7e gave (1R,3S)3-hydroxymethyl-1-indanol (1R,3S)-7e and (R)-3-hydroxymethyl-1-indanone (R)-9e, with high enantioselectivities. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.08.016
• 作为产物：
  描述：

  丁二酸二甲酯 在 palladium 10% on activated carbon 、 potassium tert-butylate 、 氢气 作用下， 以 甲醇 、 叔丁醇 为溶剂， 25.0~40.0 ℃ 、101.33 kPa 条件下， 反应 6.5h， 生成 (+/-)-2-(4-methoxybenzyl)succinic acid 1-methyl ester
  参考文献：
  名称：

  新型Arctigenin类似物的设计和合成，可改善代谢紊乱

  摘要：

  制备天然产物（-）-arctigenin（腺苷一磷酸活化蛋白激酶的活化剂）的类似物，以评估其对L6肌管中2-脱氧葡萄糖摄取的影响，并可能用于缓解代谢异常。发现外消旋arctigenin 2a显示出与（-）-arctigenin类似的摄取增强。结果，利用外消旋化合物进行了SAR研究。通过结构-活性关系研究，发现内酯基序上的关键取代模式可控制2-脱氧葡萄糖的摄取活性。结果表明，用Cl替代arctigenin的C-2苄基部分的对羟基具有对摄取活性的显着影响。具体来说，模拟2p含有p -Cl取代基的L6可以刺激L6肌管中的葡萄糖摄取和脂肪酸氧化。

  DOI：

  10.1021/acsmedchemlett.5b00007

文献信息

• 2-piperazinone-1-acetic acid derivatives and their use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US06242600B1

  公开（公告）日：2001-06-05

  The present invention provides compounds and medicines effective for prophylaxis and therapy of various diseases by controlling or inhibiting cell-adhesion. Especially, the compounds of this invention inhibit platelet aggregation action without remarkable elongation of hemorrhagic period and can be used as a safe and long-acting antithrombotic drug as compared with known substances showing the same activity. Compounds of this invention are piperazinones of the formula: wherein the ring A is a basic heterocyclic group; the ring B is a nitrogen containing heterocyclic group or a cyclic hydrocarbon group; Y is CH2; R1 is H, OH, NH2 or an hydrocarbon group which may be bound through CO, S, SO or SO2; R2 is H or a hydrocarbon group; R3 is an optionally esterified or amidated carboxyl group; and D is a lower alkyl group substituted with an optionally esterified carboxyl group; or a salt thereof.

  本发明提供了通过控制或抑制细胞粘附来预防和治疗各种疾病的化合物和药物。特别是，本发明的化合物抑制血小板聚集作用，而不会显著延长出血期，并且与显示相同活性的已知物质相比，可以作为安全且长效的抗血栓药物使用。 本发明的化合物是以下式的哌嗪酮： 其中环A是一种碱性杂环基团；环B是含氮杂环基团或环烃基团；Y是CH2；R1是H、OH、NH2或可通过CO、S、SO或SO2结合的烃基团；R2是H或烃基团；R3是可选择酯化或酰胺化的羧基团；D是取代有可选择酯化羧基团的低碳基团；或其盐。
• Phenylalanine derivative and proteinase inhibitor
  申请人：Okamoto, Shosuke

  公开号：EP0217286A1

  公开（公告）日：1987-04-08

  A phenylalanine derivative having the formula (I): where R' and R2 are independently hydrogen provided that both R' and R2 are nof hydrogen at the same time; C1-C5 alkyl which may be substituted with hydroxy, hydroxycarbonyl, C1-C4 alkoxycarbonyl, C1-C4 alkyl- mercapto, C,-C4 alkoxy, carbamoyl, sulfamoyl, pyridyl, or phenyl which may further be substituted with nitro, C1-C4 alkoxy, or halogen; C6-C3 cycloalkyl which may be substituted with hydroxy, C1-C4 alkoxy, hydroxylcarbonyl, C1-C4 alkoxycarbonyl, or C1-C4 alkyl; phenyl which may be substituted with halogen, nitro, trifluoromethyl, C,-C4 alkoxy, C1-C4 alkylmer- capto, C1-C4 alkylcarbonyl, phenylcarbonyl, hydroxycarbonyl, C1-C4 alkoxycarbonyl, carbamoyl, sulfamoyl, amidino, pyridylcarbonyl, or C1-C6 alkyl which may further be substituted with C1-C4 alkylcarbonyl, hydroxycarbonyl, or C1-C4 alkoxycarbonyl; pyridyl which may be substituted with halogen or C1-C4 alkoxy; pyrimidyl; N-benzylazacyclohexyl; and R' and R2 may form with the nitrogen atom attached thereto a ring structure as morpholino; thiomorpholino; or piperidyl which may be substituted with phenylcarbonyl, benzyl, or C1-C4 alkyl; pyrrolidyl which may be substituted with hydroxycarbonyl or C1-C4 alkoxycarbonyl; and piperidine substituted with C1-C4 alkyl, phenyl C1-C4 alkyl, phenylcarbonyl, or C,-C4 alkoxycarbonyl; X is hydrogen; nitro; amino; or -OZ wherein Z is hydrogen: C1-C4 alkyl; C2-C4 alkenyl; benzyl which may be substituted with halogen, C1-C4 alkyl, nitro, trifluoromethyl, hydroxycarbonyl, C1-C4 alkoxycarbonyl, or cyano; phenylcarbonylmethyl, pyridylmethyl; phenyl which may be substituted with nitro or halogen; pyridyl or pyrimidyl which may be substituted with nitro; phenylsulfonyl which may be substituted with C1-C4 alkyl; or benzyloxycarbonyl which may be substituted with halogen; n is 4 to 10; and the mark indicates that the configuration of the carbon may be either one of D-configuration, L-configuration and DL-configuration or a pharmaceutical acceptable salt thereof. This phenylalanine derivative is effective as a proteinase inhibitor.

  具有式（I）的苯丙氨酸衍生物： 其中 R' 和 R2 独立地为氢，但 R' 和 R2 不能同时为氢； 可被羟基、羟羰基、C1-C4 烷氧羰基、C1-C4 烷基-巯基、C,-C4 烷氧基、氨基甲酰基、氨基磺酰基、吡啶基或苯基取代的 C1-C5 烷基，可进一步被硝基、C1-C4 烷氧基或卤素取代； 可被羟基、C1-C4 烷氧基、羟基羰基、C1-C4 烷氧基羰基或 C1-C4 烷基取代的 C6-C3 环烷基； 可被卤素、硝基、三氟甲基、C,-C4 烷氧基、C1-C4 烷巯基、C1-C4 烷羰基、苯羰基、羟羰基、C1-C4 烷氧羰基、氨基甲酰基、氨基磺酰基、脒基、吡啶羰基取代的苯基，或可进一步被 C1-C4 烷羰基、羟羰基或 C1-C4 烷氧羰基取代的 C1-C6 烷基； 可被卤素或 C1-C4 烷氧基取代的吡啶基 嘧啶基； N-苄基氮杂环己基；以及 R'和R2可与相连的氮原子形成环状结构，如吗啉基；硫代吗啉基；或可被苯甲酰、苄基或C1-C4烷基取代的哌啶基； 可被羟羰基或 C1-C4 烷氧基羰基取代的吡咯烷基；以及 被 C1-C4 烷基、苯基 C1-C4 烷基、苯基羰基或 C,-C4烷氧基羰基取代的哌啶； X 是氢；硝基；氨基；或-OZ，其中 Z 是氢：C1-C4烷基；C2-C4烯基；可被卤素、C1-C4烷基、硝基、三氟甲基、羟基羰基、C1-C4烷氧基羰基或氰基取代的苄基；苯基羰基甲基、吡啶基甲基；可被硝基或卤素取代的苯基；可被硝基取代的吡啶基或嘧啶基；可被C1-C4烷基取代的苯磺酰基；或可被卤素取代的苄氧羰基； n 为 4 至 10；以及 标记表示碳的构型可以是 D-构型、L-构型和 DL-构型之一或其药物可接受盐。 这种苯丙氨酸衍生物作为蛋白酶抑制剂是有效的。
• Banerjee; Bagavant, Proceedings - Indian Academy of Sciences, Section A, 1959, # 50, p. 282,286
  作者：Banerjee、Bagavant

  DOI：——

  日期：——
• 2-PEPERAZINONE-1-ACETIC ACID DERIVATIVES AND THEIR USE
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0970071A1

  公开（公告）日：2000-01-12
• US6242600B1
  申请人：——

  公开号：US6242600B1

  公开（公告）日：2001-06-05