(3S,4S)-4-[1-(4-acetylphenyl)ethenyl]-tetrahydro-3-furanol | 1015445-30-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,4S)-4-[1-(4-acetylphenyl)ethenyl]-tetrahydro-3-furanol
• 英文别名: 1-[4-[1-[(3S,4S)-4-hydroxyoxolan-3-yl]ethenyl]phenyl]ethanone
• CAS: 1015445-30-3
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: RGJAHGZURXNLLU-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,4S)-4-[1-(4-acetylphenyl)ethenyl]-tetrahydro-3-furanol 、 (R)-(+)-α-甲氧基-α-(三氟甲基)苯乙酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Enantioselective Arylative Cyclization of Allenyl Aldehydes with Arylboronic Acids under Pd(II)-diphosphine Catalysis

  摘要：

  A Pd(OAc)(2)-SEGPHOS combination catalyzes the first enantioselective arylative cyclization of allenyl aldehydes with arylboronic acids to provide cis-fused five- and six-membered cyclic homoallylic alcohols. The excellent diastereo- and enantioselectivity and the fact that the reaction proceeds at room temperature in the absence of any additives make the process highly practical.

  DOI：

  10.1021/ol702966j
• 作为产物：
  描述：

  (2,3-butadienyloxy)acetaldehyde 、 4-乙酰基苯硼酸 在 (S)-SEGPHOS 、 palladium diacetate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以76%的产率得到(3S,4S)-4-[1-(4-acetylphenyl)ethenyl]-tetrahydro-3-furanol
  参考文献：
  名称：

  Enantioselective Arylative Cyclization of Allenyl Aldehydes with Arylboronic Acids under Pd(II)-diphosphine Catalysis

  摘要：

  A Pd(OAc)(2)-SEGPHOS combination catalyzes the first enantioselective arylative cyclization of allenyl aldehydes with arylboronic acids to provide cis-fused five- and six-membered cyclic homoallylic alcohols. The excellent diastereo- and enantioselectivity and the fact that the reaction proceeds at room temperature in the absence of any additives make the process highly practical.

  DOI：

  10.1021/ol702966j

文献信息

• Enantioselective Arylative Cyclization of Allenyl Aldehydes with Arylboronic Acids under Pd(II)-diphosphine Catalysis
  作者：Hirokazu Tsukamoto、Tomotaka Matsumoto、Yoshinori Kondo

  DOI：10.1021/ol702966j

  日期：2008.3.1

  A Pd(OAc)(2)-SEGPHOS combination catalyzes the first enantioselective arylative cyclization of allenyl aldehydes with arylboronic acids to provide cis-fused five- and six-membered cyclic homoallylic alcohols. The excellent diastereo- and enantioselectivity and the fact that the reaction proceeds at room temperature in the absence of any additives make the process highly practical.