(Z)-2-acetamido-3-(3,4-diacetoxyphenyl)acrylic acid | 65329-03-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (Z)-2-acetamido-3-(3,4-diacetoxyphenyl)acrylic acid
• 英文别名: 2-Acetamido-3-(3,4-diacetoxyphenyl)-2-propenoic acid；(Z)-2-acetamido-3-(3,4-diacetyloxyphenyl)prop-2-enoic acid
• CAS: 65329-03-5
• 化学式: C₁₅H₁₅NO₇
• 分子量: 321.287
• InChiKey: AAJVHBSGWUAGPJ-SDQBBNPISA-N

物化性质

• 熔点：
  187-188°C
• 溶解度：
  可溶于氯仿、二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (Z)-2-acetamido-3-(3,4-diacetoxyphenyl)acrylic acid 在 盐酸 、 水 、 氢气 作用下， 以 乙醇 为溶剂， 60.0~100.0 ℃ 、1.0 MPa 条件下， 反应 22.0h， 生成 alpha,3,4-三羟基-苯丙酸; 丹参素乳酸
  参考文献：
  名称：

  Improved Process for Pilot-Scale Synthesis of Danshensu ((±)-DSS) and Its Enantiomer Derivatives

  摘要：

  A pilot-scale process has been developed for green and scalable synthesis of (+/-)-beta-(3,4-dihydroxyphenyl) lactic acid ((+/-)-DSS) and their two important derivatives, namely, (+/-)-IDHP [(+/-)-isopropyl 2-hydroxy-3-(3,4-dihydroxyphenyl)propanoate] and (+/-)-DBZ [(+/-)-bornyl 2-hydroxy-3-(3,4-dihydroxyphenyl)propanoate]. Subsequent hydrogenation has been carried out by employing Raney Ni as catalyst. The improved process results in higher yields of 47.5% for (+/-)-DBZ and 49.2% for (+/-)-IDHP compared to the initial process with a yield of 12% for (+/-)-DBZ and 18% for (+/-)-IDHP in our original medicinal chemistry route. Furthermore, kilograms of optical DBZ [(-)-S-DBZ and (+)-R-DBZ, >99% ee] and IDHP [(-)-S-IDHP and (+)-R-IDHP, >99% ee] have been produced by chiral high-performance liquid chromatography in good yield (>84%).

  DOI：

  10.1021/op4002593
• 作为产物：
  描述：

  在 水 作用下， 以 丙酮 为溶剂， 以93 kg的产率得到(Z)-2-acetamido-3-(3,4-diacetoxyphenyl)acrylic acid
  参考文献：
  名称：

  Improved Process for Pilot-Scale Synthesis of Danshensu ((±)-DSS) and Its Enantiomer Derivatives

  摘要：

  A pilot-scale process has been developed for green and scalable synthesis of (+/-)-beta-(3,4-dihydroxyphenyl) lactic acid ((+/-)-DSS) and their two important derivatives, namely, (+/-)-IDHP [(+/-)-isopropyl 2-hydroxy-3-(3,4-dihydroxyphenyl)propanoate] and (+/-)-DBZ [(+/-)-bornyl 2-hydroxy-3-(3,4-dihydroxyphenyl)propanoate]. Subsequent hydrogenation has been carried out by employing Raney Ni as catalyst. The improved process results in higher yields of 47.5% for (+/-)-DBZ and 49.2% for (+/-)-IDHP compared to the initial process with a yield of 12% for (+/-)-DBZ and 18% for (+/-)-IDHP in our original medicinal chemistry route. Furthermore, kilograms of optical DBZ [(-)-S-DBZ and (+)-R-DBZ, >99% ee] and IDHP [(-)-S-IDHP and (+)-R-IDHP, >99% ee] have been produced by chiral high-performance liquid chromatography in good yield (>84%).

  DOI：

  10.1021/op4002593

文献信息

• 丹参素与H2S/NO供体结合物及其制备方法和在制药中的应用
  申请人：复旦大学

  公开号：CN111484413A

  公开（公告）日：2020-08-04

  本发明属化学制药领域，涉及中草药丹参中有效成分丹参素与H 2 S/NO供体的结合物及其制备方法和在制药中的应用，尤其是在制备防治心脑血管和炎症相关疾病药物中的用途。本发明通过体外氧化应激损伤和炎症模型实验，结果显示所述的结合物能显著抑制H 2 O 2 诱导的SH‑SY5Y细胞氧化应激损伤，对损伤细胞具有明显的保护作用；能显著抑制内毒素(LPS)诱导的小鼠腹腔巨噬细胞分泌炎性介质，减少炎症诱导的一氧化氮和炎性细胞因子的释放；体内活性实验结果显示，所述的结合物对LPS诱导的小鼠腹膜炎能改善小鼠的凝血时间，明显抑制小鼠腹腔的炎性细胞因子的释放，结果表明所述化合物可用于制备防治心脑血管疾病和炎症性疾病的药物。
• A Modified Synthesis of (±)-β-Aryllactic acids
  作者：Henry N. C. Wong、Zun Le Xu、Hson Mou Chang、Chi Ming Lee

  DOI：10.1055/s-1992-26228

  日期：——

  The synthesis of racemic forms of the reportedly active principle of Danshen, namely (±)-ß-(3,4-dihydroxyphenyl)lactic acid [(±)- 3-(3,4-dihydroxyphenyl)-2-hydroxypropanoic acid] and its seven racemic derivatives is reported.

  据报道，丹参中活性成分的外消旋形式，即（±）-ß-(3,4-二羟基苯基)乳酸[(±)-3-(3,4-二羟基苯基)-2-羟基丙酸]及其七种外消旋衍生物已成功合成。
• Deracemization and Stereoinversion of α-Amino Acids by<scp>l</scp>-Amino Acid Deaminase
  作者：Elena Rosini、Roberta Melis、Gianluca Molla、Davide Tessaro、Loredano Pollegioni

  DOI：10.1002/adsc.201700806

  日期：2017.11.10

  Enantiomerically pure α‐amino acids are compounds of primary interest for the fine chemical, pharmaceutical, and agrochemical sectors. Amino acid oxidases are used for resolving d,l‐amino acids in biocatalysis. We recently demonstrated that l‐amino acid deaminase from Proteus myxofaciens (PmaLAAD) shows peculiar features for biotechnological applications, such as a high production level as soluble

  对映体纯的α-氨基酸是精细化工，制药和农用化学领域的主要关注化合物。氨基酸氧化酶用于解析生物催化中的d，l-氨基酸。我们最近证明升-氨基从酸脱氨酶变形杆菌myxofaciens（PmaLAAD）所示特有的特征在于用于生物技术应用中，诸如高生产水平作为可溶性蛋白的大肠杆菌和稳定的与黄素辅因子结合。由于l-氨基酸脱氨酶是膜结合酶，因此以前的应用主要基于基于细胞的方法。现在，利用PmaLAAD广泛的底物特异性，可以使用多种天然和合成的纯化的酶将l-氨基酸完全转化为相应的α-酮酸：4-硝基苯丙氨酸转化最快。类似地，从外消旋溶液开始，也实现了全分辨率（ee > 99％）。值得注意的是，分别使用PmaLAAD或在213位具有甘氨酸的d-氨基酸氧化酶变体将d，l -1-萘丙氨酸解析为d-或l-对映异构体，并在将这两种酶分离后完全脱脂。共同使用。此外，完整的stereoinversion升使用PmaLAA
• SUBSTITUTED BETA-PHENYL-ALPHA-HYDROXY-PROPANOIC ACID, SYNTHESIS METHOD AND USE THEREOF
  申请人：Zheng Xiaohui

  公开号：US20090131677A1

  公开（公告）日：2009-05-21

  The present invention relates to a compound of the formula (I), wherein R 1 , R 2 and R 3 are each independently selected from H, OH, F, Cl, Br, methoxy and ethoxy; or alternatively, R 1 and R 2 together form —OCH 2 O—, R 3 is selected from H, OH, methoxy, ethoxy and halogens; R 4 is OH or acyloxy; R 5 is cycloalkoxyl, amino and substituted amino, and when R 5 is selected from amino, at least one of R 1 , R 2 and R 3 is not H. The present invention further relates to a process for synthesizing a compound of the formula (I), and use of the compound of the formula (I) in the manufacture of a medicament for the prevention or treatment of cardiovascular or cerebrovascular diseases.

  本发明涉及公式（I）的化合物，其中R1、R2和R3各自独立地选自H、OH、F、Cl、Br、甲氧基和乙氧基；或者，R1和R2一起形成-OCH2O-，R3选自H、OH、甲氧基、乙氧基和卤素；R4为OH或酰氧基；R5为环烷氧基、氨基和取代氨基，当R5选自氨基时，至少有R1、R2和R3中的一个不是H。本发明还涉及合成公式（I）化合物的方法，以及使用公式（I）化合物制造用于预防或治疗心血管或脑血管疾病的药物。
• Substituted beta-phenyl-alpha-hydroxy propanoic acid, synthesis method and use thereof
  申请人：Northwest University

  公开号：EP2514739A1

  公开（公告）日：2012-10-24

  The present invention relates to a compound of the formula (I), wherein R1, R2 and R3 are each independently selected from H, OH, F, Cl, Br, methoxy and ethoxy; or alternatively, R1 and R2 together form -OCH2O-, R3 is selected from H, OH, methoxy, ethoxy and halogens; R4 is OH or acyloxy; R5 is cycloalkoxyl, amino and substituted amino, and when R5 is selected from amino, at least one of R1, R2 and R3 is not H. The present invention further relates to a process for synthesizing a compound of the formula (I), and use of the compound of the formula (I) in the manufacture of a medicament for the prevention or treatment of cardiovascular or cerebrovascular diseases.

  本发明涉及一种式(I)化合物，其中R1、R2和R3各自独立地选自H、OH、F、Cl、Br、甲氧基和乙氧基；或者，R1和R2一起形成-OCH2O-，R3选自H、OH、甲氧基、乙氧基和卤素；R4是OH或酰氧基；R5是环烷氧基、氨基和取代氨基，当R5选自氨基时，R1、R2和R3中至少有一个不是H。本发明进一步涉及一种合成式（I）化合物的工艺，以及式（I）化合物在制造预防或治疗心脑血管疾病的药物中的用途。