(E)-3-((tert-butyldimethylsilyloxy)methyl)-5-phenylpent-4-en-1-ol | 1619980-54-9

• 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: (E)-3-((tert-butyldimethylsilyloxy)methyl)-5-phenylpent-4-en-1-ol
• CAS: 1619980-54-9
• 化学式: C₁₈H₃₀O₂Si
• 分子量: 306.521
• InChiKey: VJNMWJIIUUWWID-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.72
• 重原子数：
  21.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (E)-3-((tert-butyldimethylsilyloxy)methyl)-5-phenylpent-4-en-1-ol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以85%的产率得到(E)-2-styrylbutane-1,4-diol
  参考文献：
  名称：

  InBr3-catalyzed stereoselective synthesis of 3,4-disubstituted hexahydro-1H-furo[3,4-c]pyran derivatives

  摘要：

  An gamma,delta-unsaturated alcohol tethered with a hydroxyl group, that is, (E)-2-styrylbutane-1,4-diol (1) undergoes a smooth bicyclization with various aldehydes in the presence of 10 mol % InBr3 and at 0 degrees C to afford a novel series of hexahydro-1H-furo[3,4-c]pyran derivatives in good yields with high diastereoselectivity. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2014.05.121
• 作为产物：
  描述：

  (E)-ethyl 3-((tert-butyldimethylsilyloxy)methyl)-5-phenylpent-4-enoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以90%的产率得到(E)-3-((tert-butyldimethylsilyloxy)methyl)-5-phenylpent-4-en-1-ol
  参考文献：
  名称：

  InBr3-catalyzed stereoselective synthesis of 3,4-disubstituted hexahydro-1H-furo[3,4-c]pyran derivatives

  摘要：

  An gamma,delta-unsaturated alcohol tethered with a hydroxyl group, that is, (E)-2-styrylbutane-1,4-diol (1) undergoes a smooth bicyclization with various aldehydes in the presence of 10 mol % InBr3 and at 0 degrees C to afford a novel series of hexahydro-1H-furo[3,4-c]pyran derivatives in good yields with high diastereoselectivity. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2014.05.121

文献信息

• A Stereospecific Alkene 1,2‐Aminofunctionalization Platform for the Assembly of Complex Nitrogen‐Containing Ring Systems
  作者：Yuxiang Zhu、Matthew J. S. Smith、Wenbin Tu、John F. Bower

  DOI：10.1002/anie.202301262

  日期：——

  activated N-Boc hydroxylamines triggers aminofunctionalization-based polycyclizations of tethered alkenes. The processes involve intramolecular stereospecific aza-Prilezhaev alkene aziridination in advance of stereospecific C−N cleavage by a pendant nucleophile. Using this approach, a wide range of alkene anti-1,2-difunctionalizations can be achieved.

  TFA 促进 O−Ts 的脱保护，激活的 N-Boc 羟胺触发基于氨基官能化的链烯烃多环化。该过程涉及分子内立体特异性氮杂-Prilezhaev 烯烃氮丙啶化，然后由悬垂亲核试剂进行立体特异性 C-N 裂解。使用这种方法，可以实现范围广泛的烯烃抗-1,2-双官能化。