montagnetol | 7078-99-1

• 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: montagnetol
• 英文别名: (+/-)-Pikroerythrin；(+/-)-O¹-(4.6-Dihydroxy-2-methyl-benzoyl)-erythrit；(+/-)-erythro-1-(4.6-Dihydroxy-2-methyl-benzoyloxy)-butantriol-(2.3.4)；[(2S,3R)-2,3,4-trihydroxybutyl] 2,4-dihydroxy-6-methylbenzoate
• CAS: 7078-99-1
• 化学式: C₁₂H₁₆O₇
• 分子量: 272.255
• InChiKey: YTCVPMVUPQABQB-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  127
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (2S,3R)-2,3,4-tri-(benzyloxy)butan-1-ol 在 palladium 10% on activated carbon 、 氢气 、 sodium 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 反应 2.0h， 生成 montagnetol
  参考文献：
  名称：

  Facile syntheses of (−)-montagnetol and (−)-erythrin

  摘要：

  A novel synthetic method is introduced to prepare the biologically important montagnetol and erythrin compounds starting from a 1,3-benzodioxin-4-one, synthesized from commercially available orsellinic acid and erythritol. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.09.071

文献信息

• Stereoselective synthesis of the lichen metabolite, (+) montagnetol and its congeners as antimicrobial agents
  作者：Uppuluri Venkata Mallavadhani、Ramakrishna Boddu、Balaji B. Rathod、Prakasam Reddy Setty

  DOI：10.1080/00397911.2018.1519076

  日期：2018.12.2

  major metabolite of the fruticose lichen, Roccella montagnei was synthesized along with three of its congeners by employing highly efficient protocols. (+) Montagnetol (2 R, 3S; 11) and (-) montagnetol (2S, 3R; 5) were synthesized in 7 and 9 steps, respectively, from L-ascorbic acid. The two new congeners 3 (2 R, 3R) and 6 (2S, 3S), which differ in configuration at C-2 and C-3 positions of the (+) montagnetol

  摘要 鉴于结构多样性，果糖地衣 Roccella montagnei 的主要代谢物 (+) montagnetol 与其三个同类物一起通过高效的方案合成。(+) Montagnetol (2 R, 3S; 11) 和 (-) Montagnetol (2S, 3R; 5) 分别通过 7 步和 9 步从 L-抗坏血酸合成。两个新的同源物 3 (2 R, 3R) 和 6 (2S, 3S) 在 (+) montagnetol 的 C-2 和 C-3 位置的构型不同，是由 (-) D-酒石酸二乙酯和(+) L-酒石酸二乙酯，分别。在体外评估了合成的化合物对两种革兰氏阳性菌（金黄色葡萄球菌和大肠杆菌）和两种革兰氏阴性菌（伤寒沙门氏菌和铜绿假单胞菌）和一种真菌菌株白色念珠菌的抗菌活性。有趣的是，同源物 3 对铜绿假单胞菌显示出有希望的抗菌活性（MIC：0.062 µg/ml），而同源物 6 对白色念珠菌显示出有效的抗真菌活性（MIC：0
• Studies on the resorcylates: biomimetic total syntheses of (+)-montagnetol and (+)-erythrin
  作者：Jean-François Basset、Colin Leslie、Dieter Hamprecht、Andrew J.P. White、Anthony G.M. Barrett

  DOI：10.1016/j.tetlet.2009.11.134

  日期：2010.2

  6-(2,4-Dioxopentyl)-2,2-trimethyl-4H-1,3-dioxin-4-one on reflux in toluene gave MeCOCH2COCH2 COCH=C=O, which cyclized to 6-(2-oxopropyl)-4-hydroxy-2H-pyrin-2-one or was trapped with alcohols to produce resorcylate esters. The method was used for the synthesis of both enantiomers of montagnetol and erythrin. (c) 2009 Elsevier Ltd. All rights reserved.
• Optimism, distress, and immunologic status in HIV-infected gay men following hurricane andrew
  作者：Stacy Cruess、Michael Antoni、Kristin Kilbourn、Gail Ironson、Nancy Klimas、Mary Ann Fletcher、Andy Baum、Neil Schneiderman

  DOI：10.1207/s15327558ijbm0702_5

  日期：2000.6

  This study investigated how dispositional optimism relates to psychological and immunologic status in 40 HIV-infected gay men residing in areas of South Florida hard hit by Hurricane Andrew. In the months following the storm, participants' levers of psychological distress (hurricane-related and overall distress) and antibody titers to several herpesviruses (Herpes Simplex Virus-2, Epstein-Barr Virus [EBV], Cytomegalovirus, and Human Herpes Virus-6 [HHV-6]) were measured. Overall, participants had elevated mean levels of hurricane-specific and general distress. Higher levels of optimism were related to lower levels of depression, overall distress, and hurricane-specific posttraumatic stress disorder symptoms. After controlling for nonspecific polyclonal B cell activation, greater optimism was also associated with lower levels of circulating antibodies to EBV and HHV-6, suggesting better cellular immunologic control over these viruses among optimists. Regression analyses showed that the relation between optimism and lower EBV titers was partially mediated by the lower depression levels experienced by optimists.
• Sakurai, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1941, vol. 61, p. 108,115; dtsch. Ref. S. 45
  作者：Sakurai

  DOI：——

  日期：——
• Facile syntheses of (−)-montagnetol and (−)-erythrin
  作者：Volkan Kumbaraci、Hande Gunduz、Meric Karadeniz

  DOI：10.1016/j.tetlet.2013.09.071

  日期：2013.11

  A novel synthetic method is introduced to prepare the biologically important montagnetol and erythrin compounds starting from a 1,3-benzodioxin-4-one, synthesized from commercially available orsellinic acid and erythritol. (C) 2013 Elsevier Ltd. All rights reserved.