tert-butyl-((R)-1-cyclopropyl-but-3-enyloxy)-dimethyl-silane | 1228103-62-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: tert-butyl-((R)-1-cyclopropyl-but-3-enyloxy)-dimethyl-silane
• 英文别名: tert-butyl-[(1R)-1-cyclopropylbut-3-enoxy]-dimethylsilane
• CAS: 1228103-62-5
• 化学式: C₁₃H₂₆OSi
• 分子量: 226.434
• InChiKey: FHSRVBIUYHUKOX-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.36
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  tert-butyl-((R)-1-cyclopropyl-but-3-enyloxy)-dimethyl-silane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以87%的产率得到(R)-(-)-1-cyclopropyl-but-3-en-1-ol
  参考文献：
  名称：

  Enantioselective Synthesis of Iclaprim Enantiomers―A Versatile Approach to 2-Substituted Chiral Chromenes

  摘要：

  Both enantiomers of the DHFR inhibitor iclaprim (R)-1 and (5)-1 were synthesized from the cyclopropyl homoallyl alcohols (R)-6 and (S)-6. respectively. As key steps these transformations include a Mitsunobu reaction and the formation of the diaminopyrimidine unit prior to a novel cyclization procedure to obtain the desired chromene heterocycle. The moderate enantioselectivity of the products (R)-1 and OH is related to the Mitsunobu reaction, which unfortunately did not proceed with complete inversion or configuration.

  DOI：

  10.1021/jo100566c
• 作为产物：
  描述：

  tert-butyl-((S)-1-cyclopropyl-2-iodo-ethoxy)-dimethyl-silane 、 乙烯基溴化镁 在 copper(l) iodide 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以73%的产率得到tert-butyl-((R)-1-cyclopropyl-but-3-enyloxy)-dimethyl-silane
  参考文献：
  名称：

  Enantioselective Synthesis of Iclaprim Enantiomers―A Versatile Approach to 2-Substituted Chiral Chromenes

  摘要：

  Both enantiomers of the DHFR inhibitor iclaprim (R)-1 and (5)-1 were synthesized from the cyclopropyl homoallyl alcohols (R)-6 and (S)-6. respectively. As key steps these transformations include a Mitsunobu reaction and the formation of the diaminopyrimidine unit prior to a novel cyclization procedure to obtain the desired chromene heterocycle. The moderate enantioselectivity of the products (R)-1 and OH is related to the Mitsunobu reaction, which unfortunately did not proceed with complete inversion or configuration.

  DOI：

  10.1021/jo100566c

文献信息

• Enantioselective Synthesis of Iclaprim Enantiomers―A Versatile Approach to 2-Substituted Chiral Chromenes
  作者：Chouaib Tahtaoui、Arnold Demailly、Carole Guidemann、Cécile Joyeux、Peter Schneider

  DOI：10.1021/jo100566c

  日期：2010.6.4

  Both enantiomers of the DHFR inhibitor iclaprim (R)-1 and (5)-1 were synthesized from the cyclopropyl homoallyl alcohols (R)-6 and (S)-6. respectively. As key steps these transformations include a Mitsunobu reaction and the formation of the diaminopyrimidine unit prior to a novel cyclization procedure to obtain the desired chromene heterocycle. The moderate enantioselectivity of the products (R)-1 and OH is related to the Mitsunobu reaction, which unfortunately did not proceed with complete inversion or configuration.