(S)-3-(benzyloxy)-5-(2-methoxyphenyl)pent-4-yn-1-ol | 1384132-71-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-3-(benzyloxy)-5-(2-methoxyphenyl)pent-4-yn-1-ol
• CAS: 1384132-71-1
• 化学式: C₁₉H₂₀O₃
• 分子量: 296.366
• InChiKey: LIZOWSBTQIDIOI-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-3-(benzyloxy)-5-(2-methoxyphenyl)pent-4-yn-1-ol 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到(S)-1-(3-(benzyloxy)-5-bromopent-1-ynyl)-2-methoxybenzene
  参考文献：
  名称：

  Modular and Stereoselective Synthesis of Tetrasubstituted Helical Alkenes via a Palladium-Catalyzed Domino Reaction

  摘要：

  A highly modular and stereoselective synthesis of tetrasubstituted helical alkenes is accomplished by a Pd-catalyzed norbornene-mediated domino reaction. This protocol features the rapid assembly of four C-C bonds via sequential C-H activations and carbopalladations along with efficient access to enantiopure bromoalkyl aryl alkyne precursors using homologative alkynylation as the key transformation. Three distinct elements of stereoselectivity were observed in the preparation of the chiral helical alkenes: retention of stereochemistry of the substrates, induced helical diastereoselectivity in the alkene formation, and the exclusive exo-facial selectivity of the norbornene incorporation.

  DOI：

  10.1021/ol301495q
• 作为产物：
  描述：

  (S)-3-(benzyloxy)-5-(trimethylsilyl)pent-4-yn-1-ol 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.33h， 生成 (S)-3-(benzyloxy)-5-(2-methoxyphenyl)pent-4-yn-1-ol
  参考文献：
  名称：

  Modular and Stereoselective Synthesis of Tetrasubstituted Helical Alkenes via a Palladium-Catalyzed Domino Reaction

  摘要：

  A highly modular and stereoselective synthesis of tetrasubstituted helical alkenes is accomplished by a Pd-catalyzed norbornene-mediated domino reaction. This protocol features the rapid assembly of four C-C bonds via sequential C-H activations and carbopalladations along with efficient access to enantiopure bromoalkyl aryl alkyne precursors using homologative alkynylation as the key transformation. Three distinct elements of stereoselectivity were observed in the preparation of the chiral helical alkenes: retention of stereochemistry of the substrates, induced helical diastereoselectivity in the alkene formation, and the exclusive exo-facial selectivity of the norbornene incorporation.

  DOI：

  10.1021/ol301495q