(4R,5R)-1,5-bis(3,4-dimethoxyphenyl)-4-hydroxy-5-trimethylsilyloxypentan-1-one | 522607-81-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5R)-1,5-bis(3,4-dimethoxyphenyl)-4-hydroxy-5-trimethylsilyloxypentan-1-one
• CAS: 522607-81-4
• 化学式: C₂₄H₃₄O₇Si
• 分子量: 462.615
• InChiKey: VWCPHZBVBAKZNY-NTKDMRAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.64
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4R,5R)-1,5-bis(3,4-dimethoxyphenyl)-4-hydroxy-5-trimethylsilyloxypentan-1-one 在 四丁基二氟三苯硅酸铵 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以3.5 mg的产率得到1,5-bis(3',4'-dimethoxyphenyl)-1,2-dihydroxy-pentan-5-one
  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 吡啶 、 甲基磺酰胺 、 AD-mix-β 、 双(三甲基硅烷基)氨基钾 、 三乙胺 、 对甲苯磺酰氯 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 52.75h， 生成 (4R,5R)-1,5-bis(3,4-dimethoxyphenyl)-4-hydroxy-5-trimethylsilyloxypentan-1-one
  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.