(R)-methyl 3-(3,4-bis(benzyloxy)phenyl)-2-hydroxypropanoate | 203798-74-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R)-methyl 3-(3,4-bis(benzyloxy)phenyl)-2-hydroxypropanoate
• 英文别名: methyl (R)-3-(3,4-bis(benzyloxy)phenyl)-2-hydroxypropanoate；methyl 3-[3,4-bis(benzyloxy)phenyl]-2-hydroxypropanoate
• CAS: 203798-74-7
• 化学式: C₂₄H₂₄O₅
• 分子量: 392.452
• InChiKey: FALOZRNKHYQKFZ-OAQYLSRUSA-N

物化性质

• 沸点：
  550.7±45.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  29.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (R)-methyl 3-(3,4-bis(benzyloxy)phenyl)-2-hydroxypropanoate 在 potassium carbonate 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 allyl (R)-3-(3,4-bis(benzyloxy)phenyl)-2-hydroxypropanoate
  参考文献：
  名称：

  咖啡酸衍生物的探索：决明烯内酯，云南酸C和D的总合成以及对云南酸A和B的研究

  摘要：

  从云南丹参的根中分离出的云南酸AD，是咖啡酸的六聚体（A和B）和三聚体（C和D）组装体，具有一系列具有合成挑战性和结构上令人关注的结构域。being酸A和B除了是咖啡酸低聚物外，还是酸C和D的正式二聚体和杂二聚体加合物。在此，我们报道featuring酸C和D的第一批总合成，其特征在于它们的双环形成[2.2.2]通过简单的前体通过氧化脱芳香化作用/狄尔斯-阿尔德级联反应从一个简单的前体中分离出辛烯核，这些可能具有生物遗传学意义。另外，对由该级联反应产生的关键中间体的利用，使得能够通过意想不到的路易斯酸介导的还原来快速获得与结构相关的咖啡酸代谢物rufescenolide。最后，我们报告了广泛的模型研究结果，以形成二聚的壬二酸A和B。这些探索表明，单体片段的先天反应性不利于所需二聚键的自发形成。因此，这些更复杂的家庭成员的生物合成可能需要酶的参与。

  DOI：

  10.1021/jo4023167
• 作为产物：
  描述：

  (+)-(S)-methyl 3-(3,4-dihydroxyphenyl)-2-hydroxypropanoate 在 sodium methylate 、 potassium carbonate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 、 甲苯 为溶剂， 反应 36.0h， 生成 (R)-methyl 3-(3,4-bis(benzyloxy)phenyl)-2-hydroxypropanoate
  参考文献：
  名称：

  Synthese der enantiomeren (+)- und (−)-Rosmarinsäuremethylester

  摘要：

  DOI：

  10.1007/pl00010154

文献信息

• Synthesis of Novel Danshensu Alkamine Derivatives as Potential Anti-Myocardial Ischemia Agents
  作者：Jing-Jing Shu、Chuan Zhang、Ting-Fang Wang、Hao Zou、Lei Jin、Wei-Ying Gu、Li-Chao Zhang

  DOI：10.14233/ajchem.2014.16676

  日期：——

  Ten novel danshensu alkamine derivatives were synthesized and the preliminary biological activity of these complexes were investigated. The bioassay results indicated that some of derivatives exhibit significant activities on protecting hypoxic H9C2 cardiomyocytes.

  合成了十种新型的丹参素烷基胺衍生物，并初步探究了这些化合物的生物活性。生物测试结果表明，部分衍生物对保护缺氧H9C2心肌细胞显示出显著活性。
• First total synthesis of salvianolic acid C, tournefolic acid A, and tournefolal
  作者：Si-Da Shen、Gui-Ping Zhang、Min Lei、Li-Hong Hu

  DOI：10.3998/ark.5550190.0013.619

  日期：——

  First total synthesis of the natural product salvianolic acid C, tournefolal and tournefolic acid A has been described. The key benzofuran skeletons are prepared via selective iodination and Sonogashira reaction.

  天然产物丹酚酸 C、tournefolal 和tournefolic acid A 的首次全合成已有描述。关键的苯并呋喃骨架是通过选择性碘化和 Sonogashira 反应制备的。
• Total Synthesis of Arylnaphthalene Lignans through a Photochemical Key Step
  作者：Pablo Wessig、Dominik Badetko、Lukas Wichterich、Eric Sperlich、Alexandra Kelling

  DOI：10.1002/ejoc.202201234

  日期：2023.1.2

  The total syntheses of arylnaphthalene lignans (ANL) Vitrofolal E (1), Noralashinol C (2), and Ternifoliuslignan E (3) are described. These natural products have in common a missing substituent in 2-position of the naphthalene skeleton (2H-ANL). The key step of the syntheses is the Photo-Dehydro-Diels-Alder (PDDA) reaction between arylalkyne moieties, which are connected by a suberate linker unit.

  描述了芳基萘木脂素 ( ANL ) Vitrofolal E ( 1 )、Noralashinol C ( 2 ) 和 Ternifoliuslignan E ( 3 ) 的全合成。这些天然产物在萘骨架 ( 2H - ANL )的 2 位上有一个共同的缺失取代基。合成的关键步骤是芳基炔部分之间的光-脱氢-狄尔斯-桤木 ( PDDA ) 反应，这些部分通过辛二酸酯连接单元连接。通过 DFT 方法研究了光化学闭环区域选择性的原因。
• Cytoprotective Effects Evaluation of a Novel Danshensu Derivative DEX-018 against Oxidative Stress Injury in HUVECs
  作者：Honglei Xu、Kun He、Yi Li、Yulong Tao、Chunfang Xu、Zhenlin Hu、Tingfang Wang、Chuan Zhang

  DOI：10.1248/bpb.b19-00878

  日期：2020.5.1

  Ischemic heart disease (H-ID) is one of the most common cardiovascular diseases with high morbidity and mortality. Danshensu (DSS) is widely used in the treatment of coronary heart disease. In this study, the carboxy group of DSS was esterified with edaravone to synthesize the novel DSS derivative DEX-018 to achieve a synergistic protective effect and overcome the structural deficiency of DSS. The pharmacological effect of DEX-018 against tert-butyl hydrogen peroxide (t-BHP) induced oxidative damage in human umbilical vein endothelial cells (HUVECs) was evaluated. The results demonstrated that pretreatment with DEX-018 significantly increased cell viability and superoxide dismutase (SOD) activity and decreased the lactate dehydrogenase (LDH) leakage rate, malondialdehyde (MDA) level and intracellular reactive oxygen species (ROS) level. In addition, DEX-018 inhibited cell apoptosis and reversed the expression of apoptosis-related proteins (BcI-2, Bax, and caspase-3) in HUVECs stimulated by t-BHP Further study on the mechanism of DEX-018 revealed that the expression of p-Akt and p-extracellularsignal-regulated kinase 1/2 (ERK1/2) was increased, which suggested that DEX-018 may protect HUVECs against t-BHP induced oxidative injury viu the Akt and ERK1/2 signaling pathways. To further validate the correlation, CCK8 was used to detect cell viability after treatment with DEX-018 plus Akt inhibitor (MK2206) and phosphadylinositol 3-kinase (P13K) inhibitor (LY294002). Compared with DEX-018 alone, MK2206 or LY294002 significantly decreased cell viability of HUVECs, indicating that the protective effect of DEX-018 against t-BHP induced oxidative injury was significantly weakened. It was further verified that the antioxidant and anti-apoptotic effects of DEX-018 were partly related to the PI3K Akt signaling pathway.