[(2R,5R)-2,5-bis(methoxymethyl)pyrrolidin-1-yl]-(3-trimethylsilylfuran-2-yl)methanone | 674805-06-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [(2R,5R)-2,5-bis(methoxymethyl)pyrrolidin-1-yl]-(3-trimethylsilylfuran-2-yl)methanone
• CAS: 674805-06-2
• 化学式: C₁₆H₂₇NO₄Si
• 分子量: 325.48
• InChiKey: JMXCLINYCSYSIJ-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  51.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(2R,5R)-2,5-bis(methoxymethyl)pyrrolidin-1-yl]-(3-trimethylsilylfuran-2-yl)methanone 在 盐酸 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 4.34h， 生成 (2R)-[2-(4-methoxybenzyl)-2,5-dihydrofuran-2-yl]-methanol
  参考文献：
  名称：

  Synthesis of (±)-Secosyrin 1 and a Formal Synthesis of (−)-Secosyrin 1

  摘要：

  A short synthesis of (+/-)-secosyrin 1 is presented that starts from an electron-deficient furan; reductive alkylation under Birch conditions gives rapid access to the natural product skeleton. Two aspects of stereoselectivity are explored, the first being directed dihydroxylation of a homoallylic alcohol. Second, the facial selectivity obtained during reduction of a highly substituted cyclic ketone was examined. Finally, our synthesis was rendered enantioselective by the reduction of a furan bearing a chiral auxiliary.

  DOI：

  10.1021/ol0362313
• 作为产物：
  描述：

  三甲基氯硅烷 、 ((2R,5R)-2,5-Bis-methoxymethyl-pyrrolidin-1-yl)-furan-2-yl-methanone 在 正丁基锂 作用下， 生成 [(2R,5R)-2,5-bis(methoxymethyl)pyrrolidin-1-yl]-(3-trimethylsilylfuran-2-yl)methanone
  参考文献：
  名称：

  Synthesis of (±)-Secosyrin 1 and a Formal Synthesis of (−)-Secosyrin 1

  摘要：

  A short synthesis of (+/-)-secosyrin 1 is presented that starts from an electron-deficient furan; reductive alkylation under Birch conditions gives rapid access to the natural product skeleton. Two aspects of stereoselectivity are explored, the first being directed dihydroxylation of a homoallylic alcohol. Second, the facial selectivity obtained during reduction of a highly substituted cyclic ketone was examined. Finally, our synthesis was rendered enantioselective by the reduction of a furan bearing a chiral auxiliary.

  DOI：

  10.1021/ol0362313

文献信息

• Synthesis of (±)-Secosyrin 1 and a Formal Synthesis of (−)-Secosyrin 1
  作者：Timothy J. Donohoe、John W. Fisher、Paul J. Edwards

  DOI：10.1021/ol0362313

  日期：2004.2.1

  A short synthesis of (+/-)-secosyrin 1 is presented that starts from an electron-deficient furan; reductive alkylation under Birch conditions gives rapid access to the natural product skeleton. Two aspects of stereoselectivity are explored, the first being directed dihydroxylation of a homoallylic alcohol. Second, the facial selectivity obtained during reduction of a highly substituted cyclic ketone was examined. Finally, our synthesis was rendered enantioselective by the reduction of a furan bearing a chiral auxiliary.