(R)-4-benzyloxy-3-hydroxy-1-phenyl-1-butyne | 141939-67-5

• 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: (R)-4-benzyloxy-3-hydroxy-1-phenyl-1-butyne
• 英文别名: (2R)-4-phenyl-1-phenylmethoxybut-3-yn-2-ol
• CAS: 141939-67-5
• 化学式: C₁₇H₁₆O₂
• 分子量: 252.313
• InChiKey: BBVGXQSFWRJOOF-QGZVFWFLSA-N

物化性质

• 沸点：
  413.6±40.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  (R)-4-benzyloxy-3-hydroxy-1-phenyl-1-butyne 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以81.3%的产率得到(R)-(E)-4-benzyloxy-3-hydroxy-1-phenyl-1-butene
  参考文献：
  名称：

  An Efficient Synthesis of Optically Active 4-Benzyloxy-3-hydoroxy-1-butyne and Its Cross-Coupling Reaction

  摘要：

  An efficient procedure for the synthesis of optically active 4-benzyloxy-3-hydroxy-1-butyne (12: R = H) has been established starting with optically active tartrate ester. Cross-coupling reaction of the resulted acetylene (12: R = H) with some aromatic halides (13a approximately h) and transformation of the arylacetylenes (14a approximate h), thus obtained, into the allylic amine derivatives (17a approximate h) have also been examined via the allylic alcohol intermediates (15 a approximately h) by sequential stereoselective reduction and [3,3] sigmatropic rearrangement.

  DOI：

  10.3987/com-91-s89
• 作为产物：
  描述：

  碘苯 、 (R)-4-benzyloxy-3-hydroxy-1-butyne 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 反应 2.0h， 以90%的产率得到(R)-4-benzyloxy-3-hydroxy-1-phenyl-1-butyne
  参考文献：
  名称：

  An Efficient Synthesis of Optically Active 4-Benzyloxy-3-hydoroxy-1-butyne and Its Cross-Coupling Reaction

  摘要：

  An efficient procedure for the synthesis of optically active 4-benzyloxy-3-hydroxy-1-butyne (12: R = H) has been established starting with optically active tartrate ester. Cross-coupling reaction of the resulted acetylene (12: R = H) with some aromatic halides (13a approximately h) and transformation of the arylacetylenes (14a approximate h), thus obtained, into the allylic amine derivatives (17a approximate h) have also been examined via the allylic alcohol intermediates (15 a approximately h) by sequential stereoselective reduction and [3,3] sigmatropic rearrangement.

  DOI：

  10.3987/com-91-s89

文献信息

• The enantiospecific synthesis of chromanes and isochromanes using a variant of an intramolecular Nicholas reaction
  作者：Elizabeth Tyrrell、Khatebeh Mazloumi、Donatella Banti、Paulina Sajdak、Alex Sinclair、Adam Le Gresley

  DOI：10.1016/j.tetlet.2012.05.112

  日期：2012.8

  The enantiospecific synthesis of chromanes and isochromanes obtained from an intramolecular Nicholas cyclisation reaction is discussed. During the course of this study we observed the formation of chroman-4-ones from a CAN deprotection step of a dioxolane and this is also discussed. (c) 2012 Elsevier Ltd. All rights reserved.