benzyl orsellinate | 38862-71-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl orsellinate
• 英文别名: Benzoic acid, 2,4-dihydroxy-6-methyl-, phenylmethyl ester；benzyl 2,4-dihydroxy-6-methylbenzoate
• CAS: 38862-71-4
• 化学式: C₁₅H₁₄O₄
• 分子量: 258.274
• InChiKey: NAELFZKDZWMPBW-UHFFFAOYSA-N

物化性质

• 熔点：
  137-138 °C
• 沸点：
  449.5±30.0 °C(Predicted)
• 密度：
  1.283±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl orsellinate 在 palladium on activated charcoal 氢气 、 三氟乙酸酐 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 98.0h， 生成 皮质醇酸
  参考文献：
  名称：

  Total Synthesis of CRM646-A and -B, Two Fungal Glucuronides with Potent Heparinase Inhibition Activities

  摘要：

  CRM646-A (1) and -B (2), two fungal glucuronides with a dimeric 2,4-dihydroxy-6-alkylbenzoic acid (orcinolp-depside) aglycone showing significant heparinase and telomerase inhibition activities, were synthesized for the first time. The successful approach involved construction of the phenol glucuronidic linkage, via coupling of the orsellinate derivative 27 with glucuronate bromide 7, before assembly of the phenolic ester linkage in the depside aglycone. Attempts via direct glycosylation of the depside aglycone derivatives were not successful.

  DOI：

  10.1021/jo051384k
• 作为产物：
  描述：

  3,5-二羟基甲苯 在 sodium chlorite 、 sodium dihydrogenphosphate 、 potassium hydrogencarbonate 、 三氯氧磷 作用下， 以 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.17h， 生成 benzyl orsellinate
  参考文献：
  名称：

  Total Synthesis of CRM646-A and -B, Two Fungal Glucuronides with Potent Heparinase Inhibition Activities

  摘要：

  CRM646-A (1) and -B (2), two fungal glucuronides with a dimeric 2,4-dihydroxy-6-alkylbenzoic acid (orcinolp-depside) aglycone showing significant heparinase and telomerase inhibition activities, were synthesized for the first time. The successful approach involved construction of the phenol glucuronidic linkage, via coupling of the orsellinate derivative 27 with glucuronate bromide 7, before assembly of the phenolic ester linkage in the depside aglycone. Attempts via direct glycosylation of the depside aglycone derivatives were not successful.

  DOI：

  10.1021/jo051384k

文献信息

• Depsides as non-redox inhibitors of leukotriene B4 biosynthesis and HaCaT cell growth, 2. Novel analogues of obtusatic acid
  作者：S Kumar KC

  DOI：10.1016/s0223-5234(00)00132-x

  日期：2000.4

  acid analogues has been synthesized and evaluated as inhibitors of leukotriene B(4) (LTB(4)) biosynthesis and as antiproliferative agents. The 4-O-benzylated and the 4-O-demethylated congeners were the most potent inhibitors of LTB(4) production of the depside class of compounds, with IC(50) values in the submicromolar range. Furthermore, these compounds do not function as redox-based inhibitors because

  已合成了一系列的tus酸类似物，并被评估为白三烯B（4）（LTB（4））生物合成的抑制剂和抗增殖剂。4-O-苄基化和4-O-去甲基化同类物是最有效的Lpp（4）产生的深度类化合物的抑制剂，IC（50）值在亚微摩尔范围内。此外，这些化合物不能用作基于氧化还原的抑制剂，因为它们对稳定的自由基2,2,2-二苯基-1-吡啶并肼基不具有反应性，并且不产生可观量的脱氧核糖降解（作为衡量其生成潜力的量度）羟基自由基。一些钝化酸同源物也是角质形成细胞生长的有效抑制剂。生长抑制不是通过破坏细胞膜来介导的，
• Synthesis of New Lichen Tridepsides
  作者：John A. Elix、Vilas K. Jayanthi、Leslie F. McCaffery、Jin Yu

  DOI：10.1071/c98082

  日期：——

  The unambiguous total synthesis of ten O-methyl and/or C-hydroxy derivatives of gyrophoric acid (1) has been achieved by using the condensation of an appropriately substituted benzoic acid and benzyl lecanorate (33) or benzyl 2-O-methyllecanorate (32) in the key step.

  毫不含糊地完全合成了十种 O-甲基 和/或 C-羟基的衍生物 (1) 通过使用适当取代的苯甲酸和柠檬酸苄酯（33）或柠檬酸苄酯 苯甲酸和柠檬酸苄酯（33）或 2-O-甲基柠檬酸苄酯（33 2-O-甲基柠檬酸苄酯（32）进行缩合。
• Deconstruction of 18β-glycyrrhetinic acid into gram scale multifunctional chiral synthons
  作者：Ramesh Gorre、Chandra Shekhar、Nandikolla Krishna Chaitanya、Srivari Chandrasekhar

  DOI：10.1016/j.tetlet.2023.154715

  日期：2023.9

  The transformation of 18β-glycyrrhetinic acid into two significant chiral synthons has been successfully showcased employing gentle reaction conditions. The effectiveness of one of these chiral synthons has been exhibited by utilizing it as a key building block for the synthesis of tetracyclic meroterpenoid natural products (+)-hongoquercins A and B.

  18β-甘草次酸转化为两个重要的手性合成子已在温和的反应条件下成功展示。这些手性合成子之一的有效性已通过将其用作合成四环类萜天然产物 (+)-红槲皮素 A 和 B 的关键构件而得到展示。
• Sustaining potato crop, land and industry health beyond the year 2000: Current issues and future needs
  作者：H. W. (Bud) Platt、E. S. Plissey、G. R. MacKay、M. Adams、M. K. Hinkle、E. MacDonald

  DOI：10.1007/bf02853955

  日期：2000.9
• Kato,T.; Hozumi,T., Chemical and pharmaceutical bulletin, 1972, vol. 20, p. 1574 - 1578
  作者：Kato,T.、Hozumi,T.

  DOI：——

  日期：——