(2R)-2-[(R)-butoxy-(3,4-dimethoxyphenyl)methyl]oxirane | 522607-78-9

• 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: (2R)-2-[(R)-butoxy-(3,4-dimethoxyphenyl)methyl]oxirane
• CAS: 522607-78-9
• 化学式: C₁₅H₂₂O₄
• 分子量: 266.337
• InChiKey: CHMHNBVFEIJTNP-HUUCEWRRSA-N

物化性质

• 沸点：
  363.1±42.0 °C(Predicted)
• 密度：
  1.092±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-二甲氧基苯乙酮 、 (2R)-2-[(R)-butoxy-(3,4-dimethoxyphenyl)methyl]oxirane 在 双(三甲基硅烷基)氨基钾 、 三氟化硼乙醚 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以26%的产率得到
  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 、 sodium hydride 、 对甲苯磺酰氯 作用下， 以 四氢呋喃 、 水 、 二甲基亚砜 、 叔丁醇 为溶剂， 反应 52.67h， 生成 (2R)-2-[(R)-butoxy-(3,4-dimethoxyphenyl)methyl]oxirane
  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.