(3R,4S,5R)-3,4,5-triacetoxycyclohex-1-ene-1-carboxylic acid | 98167-08-9

• 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: (3R,4S,5R)-3,4,5-triacetoxycyclohex-1-ene-1-carboxylic acid
• 英文别名: (3R,4S,5R)-3,4,5-triacetyloxycyclohexene-1-carboxylic acid
• CAS: 98167-08-9
• 化学式: C₁₃H₁₆O₈
• 分子量: 300.265
• InChiKey: YNYSJHWVHQBIKV-IJLUTSLNSA-N

物化性质

• 沸点：
  372.4±41.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3R,4S,5R)-3,4,5-triacetoxycyclohex-1-ene-1-carboxylic acid 在 正丁基锂 、 氯化亚砜 作用下， 以 氯仿 为溶剂， 反应 4.0h， 生成 3,4,5-tri-O-acetyl shikimate de phenyle
  参考文献：
  名称：

  Delfourne, Evelyne; Despeyroux, Pierre; Gorrichon, Liliane, Journal of Chemical Research, Miniprint, 1991, # 3, p. 532 - 544

  摘要：

  DOI：
• 作为产物：
  描述：

  2',3,4,5-Tetra-O-acetyl-scyllo-chinicol 在 吡啶 、 chromium(VI) oxide 、 溶剂黄146 、 三氯氧磷 作用下， 生成 (3R,4S,5R)-3,4,5-triacetoxycyclohex-1-ene-1-carboxylic acid
  参考文献：
  名称：

  Grewe et al., Angewandte Chemie, 1957, vol. 69, p. 61

  摘要：

  DOI：

文献信息

• Photoelectrocyclization Reactions of Amidonaphthoquinones
  作者：Jinya Yin、Michael B. Landward、Jon D. Rainier

  DOI：10.1021/acs.joc.9b03417

  日期：2020.3.20

  Readily available acrylamide naphthoquinones can be converted into the corresponding aza-anthraquinones using 6π-photoelectrocyclization reactions. Not only do these reactions not proceed thermally but, as demonstrated here, they can also be used to generate a range of aza-anthraquinone and aza-tetracycline derivatives including the natural products griffithazanone A and marcanine A. Several of the

  使用6π-光电环化反应，可以将现成的丙烯酰胺萘醌转化为相应的氮杂蒽醌。这些反应不仅不会进行热反应，而且，如此处所示，它们还可用于生成一系列氮杂蒽蒽醌和氮杂四环素衍生物，包括天然产物格里菲扎氮酮A和marcanineA。这项工作显示出抗菌活性。
• Design, synthesis and biological evaluation of novel tetrahydroisoquinoline derivatives as potential PDE4 inhibitors
  作者：Gaopeng Song、Dongsheng Zhao、Dekun Hu、Yasheng Li、Hongwei Jin、Zining Cui

  DOI：10.1016/j.bmcl.2015.08.043

  日期：2015.10

  The design, synthesis, and biological evaluation of new phosphodiesterase type 4 (PDE4) inhibitors, which possessed 7-(cyclopentyloxy)-6-methoxy 1,2,3,4-tetrahydroisoquinoline ring, were described. Compound 8 [(7-cyclopentyloxy)-6-methoxy-3,4-dihydroisoquinolin-2(1H)-yl)(4-hydroxy-3-methoxy-phenyl)methanone] showed the best inhibitory activity and good selectivity against PDE4B. The docking results

  描述了具有7-（环戊氧基）-6-甲氧基1,2,3,4-四氢异喹啉环的新型4型磷酸二酯酶（PDE4）抑制剂的设计，合成和生物学评估。化合物8 [（7-环戊氧基）-6-甲氧基-3,4-二氢异喹啉-2（1 H）-基）（4-羟基-3-甲氧基-苯基）甲酮显示出最佳的抑制活性和对PDE4B的良好选择性。对接结果表明，化合物8的邻苯二酚二醚部分在与PDE4B蛋白形成完整的氢键方面起着关键作用，而分子的其余部分延伸到催化域中以阻止cAMP的进入并为抑制PDE4奠定了基础。 。化合物8 基于初步的结构-活性关系和分子模型研究，作为进一步研究的热门化合物将有很大的希望。
• Protection of COOH and OH groups in acid, base and salt free reactions
  作者：Xiaotao Zhu、Bo Qian、Rongbiao Wei、Jian-Dong Huang、Hongli Bao

  DOI：10.1039/c8gc00037a

  日期：——

  We report an iron-catalyzed general functional group protection method with inexpensive reagents. This environmentally benign process does not use acids or bases, and does not produce waste products. Further purification beyond filtration and evaporation is, in most cases, unnecessary. Free COOH and OH groups can be protected in a one-pot reaction.

  我们报告了一种廉价的试剂铁催化的一般官能团保护方法。这种对环境无害的过程不会使用酸或碱，也不会产生废品。在大多数情况下，无需进行除过滤和蒸发之外的进一步纯化。一锅反应可保护游离的COOH和OH基团。
• [EN] NOVEL CATIONIC AMPHIPHILES WITH MANNOSE-MIMICKING HEAD-GROUPS AND A PROCESS FOR THE PREPARATION THEREOF<br/>[FR] NOUVEAUX AMPHIPHILES CATIONIQUES À TÊTES POLAIRES IMITANT LA MANNOSE, ET LEURS MÉTHODES DE PRÉPARATION
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2012035557A1

  公开（公告）日：2012-03-22

  The present invention discloses novel cationic amphiphiles containing mannose-mimicking shikimic and quinic acid head-groups and a process for preparing cationic amphiphiles with mannose-mimicking polar head-groups such as, shikimic and quinic acids. The findings described herein also demonstrate that compounds of the present invention can target model DNA vaccines to antigen presenting cells (APCs) such as macrophages and dendritic cells (DCs), via mannose receptors expressed on the cell surface of APCs. The cationic amphiphiles disclosed herein show enhanced cellular and humoral immune response compared to their mannosyl counterpart in dendritic cell (DC, the most professional APC) based genetic immunization in mice. Cationic amphiphiles with mannose-mimicking quinic and shikic acid head-groups described in the present invention are likely to find future applications in the field of genetic immunization.

  本发明公开了包含类似于甘露糖的樟脑酸和奎尼酸头基的新型阳离子两性分子，以及一种制备具有类似于甘露糖极性头基的阳离子两性分子（如樟脑酸和奎尼酸）的方法。本文描述的研究结果还表明，本发明的化合物可以通过APC（抗原呈递细胞）如巨噬细胞和树突状细胞表面上表达的甘露糖受体，将模型DNA疫苗定位到目标细胞。与其甘露基对照相比，本文披露的阳离子两性分子在小鼠基因免疫中表现出更强的细胞和体液免疫应答。本发明中描述的具有类似于甘露糖的奎尼酸和樟脑酸头基的阳离子两性分子可能在基因免疫领域找到未来的应用。
• [EN] MANNOSE-RECEPTOR SELECTIVE LYSINYLATED CATIONIC AMPHIPHILES AND A PROCESS FOR PREPARATION THEREOF<br/>[FR] AMPHIPHILES CATIONIQUES LYSINYLÉS SÉLECTIFS DU RÉCEPTEUR AU MANNOSE ET LEUR PROCÉDÉ DE PRÉPARATION
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2014106856A1

  公开（公告）日：2014-07-10

  The present invention relates to the mannose - receptor selective lysinylated cationic amphiphile and a process for preparation thereof. The compounds of the present invention can target DNA vaccines to antigen presenting cells (APCs) such as macrophages and dendritic cells (DCs), via mannose receptors expressed on the cell surface of APCs. The cationic amphiphiles disclosed herein show enhanced cellular and humoral immune response compared to their mannosyl counterparts in genetic immunization in mice. The present invention discloses that immunization with electrostatic complexes (lipoplexes) of DNA vaccines encoding melanoma antigens (gp100 and tyrosinase) and liposome of the presently described novel lysinylated cationic amphiphiles with mannose-mimicking shikimoyl head-groups provides long-lasting (100 days post melanoma tumor challenge) protective immunity in all immunized mice. Cationic amphiphiles with mannose-mimicking shikimoyl head-groups described in the present invention are likely to find future applications in the field of genetic immunization.

  本发明涉及甘露糖受体选择性赖氨酸化阳离子两性分子及其制备方法。本发明的化合物可以通过存在于抗原呈递细胞（APCs）如巨噬细胞和树突细胞（DCs）表面的甘露糖受体，将DNA疫苗靶向到这些细胞。本文披露的阳离子两性分子与其甘露基对照物相比，在小鼠基因免疫中显示出增强的细胞和体液免疫应答。本发明揭示，使用编码黑色素瘤抗原（gp100和酪氨酸酶）的DNA疫苗的静电复合物（脂质复合物）和目前描述的具有模拟甘露基的梭梗素头基的新型赖氨酸化阳离子两性分子的脂质体免疫，可以在所有免疫小鼠中提供持久的（挑战黑色素瘤肿瘤后100天）保护免疫。本发明中描述的具有模拟甘露基的梭梗素头基的阳离子两性分子可能在基因免疫领域找到未来的应用。