(2S,3R)-(-)-erythrin | 480-57-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: (2S,3R)-(-)-erythrin
• 英文别名: erythrin；Erythrin；[3-hydroxy-5-methyl-4-[(2S,3R)-2,3,4-trihydroxybutoxy]carbonylphenyl] 2,4-dihydroxy-6-methylbenzoate
• CAS: 480-57-9
• 化学式: C₂₀H₂₂O₁₀
• 分子量: 422.389
• InChiKey: BUBBEHCXSMCYNY-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  174
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2S,3R)-(-)-erythrin 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 以47%的产率得到
  参考文献：
  名称：

  5-脱羧二苯并呋喃的新进入通过地衣对-depside，红蛋白的Smiles重排

  摘要：

  从地衣 Roccella montagnei 中以 7.3% 的产率分离出的红蛋白通过 Smiles 重排转化为一系列二苯醚。那些在 C-1 处具有游离羧酸的化合物在 Pd(OAc)2 存在下经历了一种新型的脱羧氧化环化反应，生成 5-脱羧基二苯并呋喃。测定了所有化合物的抗氧化和β-葡萄糖醛酸酶抑制活性。

  DOI：

  10.3184/030823410x12677394014276
• 作为产物：
  描述：

  2,4-二羟基-6-甲基苯甲酸 在 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 氢气 、 sodium 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 乙酸乙酯 、 丙酮 、 甲苯 为溶剂， 反应 40.0h， 生成 (2S,3R)-(-)-erythrin
  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

• Novel Entry into 5-Decarboxydibenzofurans via Smiles Rearrangement of the Lichen Para-Depside, Erythrin
  作者：Vinitha M. Thadhani、Muhammad Iqbal Choudhary、Raymond J. Andersen、Veranja Karunaratne

  DOI：10.3184/030823410x12677394014276

  日期：2010.3

  Erythrin, isolated in 7.3% yield from the lichen Roccella montagnei, was converted via a Smiles rearrangement to a series of diphenyl ethers. Those with a free carboxylic acid at C-1 underwent a novel decarboxylative oxidative cyclisation in the presence of Pd(OAc)2 to produce 5-decarboxydibenzofurans. All compounds were assayed for their antioxidant and β-glucuronidase enzyme inhibitory activity.

  从地衣 Roccella montagnei 中以 7.3% 的产率分离出的红蛋白通过 Smiles 重排转化为一系列二苯醚。那些在 C-1 处具有游离羧酸的化合物在 Pd(OAc)2 存在下经历了一种新型的脱羧氧化环化反应，生成 5-脱羧基二苯并呋喃。测定了所有化合物的抗氧化和β-葡萄糖醛酸酶抑制活性。
• 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.