2-(3-hydroxybenzylidene)malonic acid dimethyl ester

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-(3-hydroxybenzylidene)malonic acid dimethyl ester
• 英文别名: Dimethyl 2-[(3-hydroxyphenyl)methylidene]propanedioate
• 化学式: C₁₂H₁₂O₅
• 分子量: 236.224
• InChiKey: BGKFEHNNKXCGBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 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-(3-hydroxybenzylidene)malonic acid dimethyl ester 在 Bacillus licheniformis protease 、 盐酸 、 5%-palladium/activated carbon 、 palladium 10% on activated carbon 、 氢气 、 sodium methylate 、 potassium carbonate 、 sodium hydroxide 、 锌 作用下， 以 甲醇 、 aq. phosphate buffer 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 10.0~100.0 ℃ 、120.0 kPa 条件下， 反应 153.5h， 生成 L-M-酪氨酸
  参考文献：
  名称：

  Optimized Synthesis of l-m-Tyrosine Suitable for Chemical Scale-Up

  摘要：

  This paper demonstrates how L-m-tyrosine 1 can be synthesized on larger-scale via enzyme-catalyzed kinetic resolution of N-acyl m-tyrosine methyl ester 4. N-Acyl m-tyrosine methyl ester 4 was prepared by a modification of Erlenmeyer's azalactone synthesis followed by hydrogenation of the resultant dehydroamino acid 12. The optimized four-step synthesis utilizes cheap and readily available starting materials and circumvents difficult purification protocols.

  DOI：

  10.1021/op700093y
• 作为产物：
  描述：

  间羟基苯甲醛 、 丙二酸二甲酯 在 吡啶 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 2-(3-hydroxybenzylidene)malonic acid dimethyl ester
  参考文献：
  名称：

  Optimized Synthesis of l-m-Tyrosine Suitable for Chemical Scale-Up

  摘要：

  This paper demonstrates how L-m-tyrosine 1 can be synthesized on larger-scale via enzyme-catalyzed kinetic resolution of N-acyl m-tyrosine methyl ester 4. N-Acyl m-tyrosine methyl ester 4 was prepared by a modification of Erlenmeyer's azalactone synthesis followed by hydrogenation of the resultant dehydroamino acid 12. The optimized four-step synthesis utilizes cheap and readily available starting materials and circumvents difficult purification protocols.

  DOI：

  10.1021/op700093y

文献信息

• Pheny (alkyl)carboxylic acid derivatives and dionic phenylalkylheterocyclic derivatives and their use as medicines with serum glucose and/or serum lipid lowering activity
  申请人：Giannessi Fabio

  公开号：US20050032787A1

  公开（公告）日：2005-02-10

  Formula (I) compounds are described: Where the groups are as defined here below, and their use as medinies, particularly as serum glucose and serum lipid lowering agents. Said medicines are useful for the prophylaxis and treatment of diabetes, particularly type 2, and its complications, Syndrome X, the various forms of insulin resistance, and hyperlipidaemias, and present reduced side effects, and, particularly, reduced or no liver toxicity.

  描述了公式(I)化合物：其中各组如下所定义，并且它们的用途作为药物，特别是作为血清葡萄糖和血清脂质降低剂。所述药物对于预防和治疗糖尿病，特别是2型糖尿病及其并发症，综合征X，各种形式的胰岛素抵抗和高脂血症非常有用，并且具有减少的副作用，特别是减少或无肝毒性。
• PHENY(ALKYL)CARBOXYLIC ACID DERIVATIVES AND DIONIC PHENYLALKYLHETEROCYCLIC DERIVATIVES AND THEIR USE AS MEDICINES WITH SERUM GLUCOSE AND/OR SERUM LIPID LOWERING ACTIVITY
  申请人：SIGMA-TAU IndustrieFarmaceutiche Riunite S.p.A.

  公开号：EP1465858A2

  公开（公告）日：2004-10-13
• US5951841A
  申请人：——

  公开号：US5951841A

  公开（公告）日：1999-09-14
• [EN] PHENY(ALKYL)CARBOXYLIC ACID DERIVATIVES AND DIONIC PHENYLALKYLHETEROCYCLIC DERIVATIVES AND THEIR USE AS MEDICINES WITH SERUM GLUCOSE AND/OR SERUM LIPID LOWERING ACTIVITY<br/>[FR] DERIVES D'ACIDE PHENY(ALKYL)CARBOXYLIQUE ET DERIVES PHENYLALKYLHETEROCYCLIQUES DIONIQUES ET LEUR UTILISATION COMME MEDICAMENTS A ACTIVITE D'ABAISSEMENT DE NIVEAU DE GLUCOSE SERIQUE ET/OU LIPIDES SERIQUES
  申请人：SIGMA TAU IND FARMACEUTI

  公开号：WO2003059864A2

  公开（公告）日：2003-07-24

  Formula (I) compounds are described: Where the groups are as defined here below, and their use as medinies, particularly as serum glucose and serum lipid lowering agents. Said medicines are useful for the prophylaxis and treatment of diabetes, particularly type 2, and its complications, Syndrome X, the various forms of insulin resistance, and hyperlipidaemias, and present reduced side effects, and, particularly, reduced or no liver toxicity.
• Optimized Synthesis of <scp>l</scp>-<i>m</i>-Tyrosine Suitable for Chemical Scale-Up
  作者：Cara E. Humphrey、Markus Furegati、Kurt Laumen、Luigi La Vecchia、Thomas Leutert、J. Constanze D. Müller-Hartwieg、Markus Vögtle

  DOI：10.1021/op700093y

  日期：2007.11.1

  This paper demonstrates how L-m-tyrosine 1 can be synthesized on larger-scale via enzyme-catalyzed kinetic resolution of N-acyl m-tyrosine methyl ester 4. N-Acyl m-tyrosine methyl ester 4 was prepared by a modification of Erlenmeyer's azalactone synthesis followed by hydrogenation of the resultant dehydroamino acid 12. The optimized four-step synthesis utilizes cheap and readily available starting materials and circumvents difficult purification protocols.