5-(2-((3-tert-butyldimethylsiloxy)propynyl)phenyl)-4-pentynol | 153165-13-0

• 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: 5-(2-((3-tert-butyldimethylsiloxy)propynyl)phenyl)-4-pentynol
• 英文别名: 5-[2-[3-[tert-butyl(dimethyl)silyl]oxyprop-1-ynyl]phenyl]pent-4-yn-1-ol
• CAS: 153165-13-0
• 化学式: C₂₀H₂₈O₂Si
• 分子量: 328.527
• InChiKey: IARBEKGWESAPBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  5-(2-((3-tert-butyldimethylsiloxy)propynyl)phenyl)-4-pentynol 在 Celite 、 四丁基氟化铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 pyridinium chlorochromate 、 lithium chloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.17h， 生成 methyl 7-<2-(3-hydroxy-1-propynyl)phenyl>hept-2-en-6-ynoate
  参考文献：
  名称：

  Synthetic studies of the tandem enediyne-mono- and bisradical cyclizations

  摘要：

  The readily synthesized enediynes 12a-j possessing a tethered olefin radical acceptor can participate in a tandem enediyne-radical cyclization to yield dibydrobenzindene derivatives 14a-j. In the present study, the scope of this reaction was expanded to include a wide variety of olefin acceptors. Substitution at both ends of olefin leads to the formation of two diastereomers 14b and 14c in a 3.5:1 ratio when R3 is Me and R2 is CO2Me. The structures of the dihydrobenzindene products 14b and 14c were confirmed by generating a radical from 25 by a tributyltin hydride reaction which undergoes radical cyclization; this radical is similar to the enediyne-generated radical, which also cyclizes. It was shown that, in 14i and 14j, a substituent at R1 slowed the reaction but still resulted in a good to excellent yield of product. A tandem enediyne-6-exo-radical cyclization of 16 was also carried out but did not work as well as its 5-exo counterpart 12a. Finally, an enediyne 33 containing two olefinic tethers was cyclized in a process to form tetracycle 34 where three rings were formed in one synthetic operation.

  DOI：

  10.1021/ja00078a013
• 作为产物：
  描述：

  1,2-二碘苯 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 反应 0.33h， 生成 5-(2-((3-tert-butyldimethylsiloxy)propynyl)phenyl)-4-pentynol
  参考文献：
  名称：

  Synthetic studies of the tandem enediyne-mono- and bisradical cyclizations

  摘要：

  The readily synthesized enediynes 12a-j possessing a tethered olefin radical acceptor can participate in a tandem enediyne-radical cyclization to yield dibydrobenzindene derivatives 14a-j. In the present study, the scope of this reaction was expanded to include a wide variety of olefin acceptors. Substitution at both ends of olefin leads to the formation of two diastereomers 14b and 14c in a 3.5:1 ratio when R3 is Me and R2 is CO2Me. The structures of the dihydrobenzindene products 14b and 14c were confirmed by generating a radical from 25 by a tributyltin hydride reaction which undergoes radical cyclization; this radical is similar to the enediyne-generated radical, which also cyclizes. It was shown that, in 14i and 14j, a substituent at R1 slowed the reaction but still resulted in a good to excellent yield of product. A tandem enediyne-6-exo-radical cyclization of 16 was also carried out but did not work as well as its 5-exo counterpart 12a. Finally, an enediyne 33 containing two olefinic tethers was cyclized in a process to form tetracycle 34 where three rings were formed in one synthetic operation.

  DOI：

  10.1021/ja00078a013