(1R,2R)-1-(3,4-二甲氧基苯基)丙烷-1,2,3-三醇 | 499135-15-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (1R,2R)-1-(3,4-二甲氧基苯基)丙烷-1,2,3-三醇
• 英文名称: 1-(3,4-dimethoxyphenyl)-1(R),2(R),3-trihydroxypentane
• 英文别名: (1'R,2'R)-4-O-methylguaiacyl glycerol；(1'R,2'R)-O-methylguaiacyl glycerol；(1R,2R)-1-(3,4-Dimethoxyphenyl)propane-1,2,3-triol
• CAS: 499135-15-8
• 化学式: C₁₁H₁₆O₅
• 分子量: 228.245
• InChiKey: NHELEQGRSPWRNT-LDYMZIIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,2R)-1-(3,4-二甲氧基苯基)丙烷-1,2,3-三醇 在 吡啶 、 对甲苯磺酰氯 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 以71%的产率得到(R)-(3,4-dimethoxyphenyl)-[(2R)-oxiran-2-yl]methanol
  参考文献：
  名称：

  Mild, Fast, and Stereoselective Epoxide Opening by Ketone Enolate Anions. Application to Synthesis of the Norlignan Curculigine

  摘要：

  We report here that (1) enolate anions of five- to seven-membered cycloalkanones nucleophilically open cyclopentene and cyclohexene oxides in 57-76% yields and with 4-8:1 diastereoselectivity; (2) enolate anions formed regiospecifically via kinetic deprotonation of 2-cyclohexenone and 2-cycloheptenone open cyclohexene oxide in 60-62% yields and with 32-95:1 diastereoselectivity; and (3) an aryl methyl ketone enolate anion opens a monosubstituted epoxide as the key step in a short synthesis of the gamma-hydroxyketone (GHK) aglycon of the natural product curculigine.

  DOI：

  10.1021/jo020744q
• 作为产物：
  描述：

  (E)-3-(3,4-二甲氧基苯基)烯丙醇 在 甲基磺酰胺 、 AD-mix-β 作用下， 以 水 、 叔丁醇 为溶剂， 反应 48.0h， 以92%的产率得到(1R,2R)-1-(3,4-二甲氧基苯基)丙烷-1,2,3-三醇
  参考文献：
  名称：

  Mild, Fast, and Stereoselective Epoxide Opening by Ketone Enolate Anions. Application to Synthesis of the Norlignan Curculigine

  摘要：

  We report here that (1) enolate anions of five- to seven-membered cycloalkanones nucleophilically open cyclopentene and cyclohexene oxides in 57-76% yields and with 4-8:1 diastereoselectivity; (2) enolate anions formed regiospecifically via kinetic deprotonation of 2-cyclohexenone and 2-cycloheptenone open cyclohexene oxide in 60-62% yields and with 32-95:1 diastereoselectivity; and (3) an aryl methyl ketone enolate anion opens a monosubstituted epoxide as the key step in a short synthesis of the gamma-hydroxyketone (GHK) aglycon of the natural product curculigine.

  DOI：

  10.1021/jo020744q

文献信息

• Mild, Fast, and Stereoselective Epoxide Opening by Ketone Enolate Anions. Application to Synthesis of the Norlignan Curculigine
  作者：Gary H. Posner、John P. Maxwell、Mehmet Kahraman

  DOI：10.1021/jo020744q

  日期：2003.4.1

  We report here that (1) enolate anions of five- to seven-membered cycloalkanones nucleophilically open cyclopentene and cyclohexene oxides in 57-76% yields and with 4-8:1 diastereoselectivity; (2) enolate anions formed regiospecifically via kinetic deprotonation of 2-cyclohexenone and 2-cycloheptenone open cyclohexene oxide in 60-62% yields and with 32-95:1 diastereoselectivity; and (3) an aryl methyl ketone enolate anion opens a monosubstituted epoxide as the key step in a short synthesis of the gamma-hydroxyketone (GHK) aglycon of the natural product curculigine.