(6,7-Dimethoxy-2-benzofuran-1-yl)oxy-trimethylsilane | 1221683-40-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异苯并呋喃
• 英文名称: (6,7-Dimethoxy-2-benzofuran-1-yl)oxy-trimethylsilane
• 英文别名: (6,7-dimethoxy-2-benzofuran-1-yl)oxy-trimethylsilane
• CAS: 1221683-40-4
• 化学式: C₁₃H₁₈O₄Si
• 分子量: 266.369
• InChiKey: JFPRUZOBUZZUFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  40.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7,8-二氢-[1,3]二氧代[4,5-g]异喹啉 、 (6,7-Dimethoxy-2-benzofuran-1-yl)oxy-trimethylsilane 、 碘甲烷 在 1-butyl-3-methylimidazolium Tetrafluoroborate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 (±)-α-hydrastine 、 北美黄连碱
  参考文献：
  名称：

  Short synthesis of noscapine, bicuculline, egenine, capnoidine, and corytensine alkaloids through the addition of 1-siloxy-isobenzofurans to imines

  摘要：

  A concise diastereotioselective strategy for the synthesis of noscapine, bicuculiine, and egenine (1a-c), as well as capnoidine and corytensine (2a,b), was developed using diastereoselective addition of 1-siloxy-isobenzofurans 4a and 4b to immium ion 5 in a one-pot approach. The synthesis features the use of imine 13 obtained through Bischler-Napieralsky reaction from airline 11. The addition of ionic liquids as addictives in the reactions afforded erythro configuration in major adduct compounds. The synthetic route can also be applied in the total synthesis of promising tubulin binding agent EM105 (3). (C) 2010 Elseviet Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.01.104
• 作为产物：
  描述：

  三甲基氯硅烷 、 6,7-Dimethoxy-2-benzofuran-1-ol 以 四氢呋喃 为溶剂， 反应 16.25h， 生成 (6,7-Dimethoxy-2-benzofuran-1-yl)oxy-trimethylsilane
  参考文献：
  名称：

  Short synthesis of noscapine, bicuculline, egenine, capnoidine, and corytensine alkaloids through the addition of 1-siloxy-isobenzofurans to imines

  摘要：

  A concise diastereotioselective strategy for the synthesis of noscapine, bicuculiine, and egenine (1a-c), as well as capnoidine and corytensine (2a,b), was developed using diastereoselective addition of 1-siloxy-isobenzofurans 4a and 4b to immium ion 5 in a one-pot approach. The synthesis features the use of imine 13 obtained through Bischler-Napieralsky reaction from airline 11. The addition of ionic liquids as addictives in the reactions afforded erythro configuration in major adduct compounds. The synthetic route can also be applied in the total synthesis of promising tubulin binding agent EM105 (3). (C) 2010 Elseviet Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.01.104

文献信息

• Short synthesis of noscapine, bicuculline, egenine, capnoidine, and corytensine alkaloids through the addition of 1-siloxy-isobenzofurans to imines
  作者：Maria Del Pilar C. Soriano、Nagula Shankaraiah、Leonardo Silva Santos

  DOI：10.1016/j.tetlet.2010.01.104

  日期：2010.3

  A concise diastereotioselective strategy for the synthesis of noscapine, bicuculiine, and egenine (1a-c), as well as capnoidine and corytensine (2a,b), was developed using diastereoselective addition of 1-siloxy-isobenzofurans 4a and 4b to immium ion 5 in a one-pot approach. The synthesis features the use of imine 13 obtained through Bischler-Napieralsky reaction from airline 11. The addition of ionic liquids as addictives in the reactions afforded erythro configuration in major adduct compounds. The synthetic route can also be applied in the total synthesis of promising tubulin binding agent EM105 (3). (C) 2010 Elseviet Ltd. All rights reserved.