3-hydroxy-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylmethyl]-2-cyclopentenone | 1039078-54-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-hydroxy-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylmethyl]-2-cyclopentenone
• 英文别名: 3-Hydroxy-2-[[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl]cyclopent-2-en-1-one
• CAS: 1039078-54-0
• 化学式: C₁₈H₂₃BO₄
• 分子量: 314.189
• InChiKey: BMUQFQQKZGAZEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-hydroxy-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylmethyl]-2-cyclopentenone 、 丁烯酮 在 L-脯氨酸 作用下， 以 二甲基亚砜 为溶剂， 反应 168.0h， 生成 、 (3aS,7aR)-3a-hydroxy-7a-[[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl]-3,4,6,7-tetrahydro-2H-indene-1,5-dione
  参考文献：
  名称：

  Synthesis of 7a-Substituted Hajos−Wiechert Ketone Analogues

  摘要：

  A general and efficient route to 2-substituted 1,3-cyclopentadiones 3 has been developed. This operationally simple, two-step procedure is amenable to mulfigram scale preparations of these useful synthetic intermediates. These compounds are then transformed to previously unknown, higher analogues of the Hajos-Parrish-Eder-Sauer-Wiechert ketone (enone 1, R = Me) following an enantioselective Robinson annulation.

  DOI：

  10.1021/jo800638s
• 作为产物：
  描述：

  3-Hydroxy-2-[pyrrolidin-1-yl-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl]cyclopent-2-en-1-one 在 palladium on activated charcoal 氢气 作用下， 以 2,2,2-三氟乙醇 为溶剂， 反应 20.0h， 以79%的产率得到3-hydroxy-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylmethyl]-2-cyclopentenone
  参考文献：
  名称：

  Synthesis of 7a-Substituted Hajos−Wiechert Ketone Analogues

  摘要：

  A general and efficient route to 2-substituted 1,3-cyclopentadiones 3 has been developed. This operationally simple, two-step procedure is amenable to mulfigram scale preparations of these useful synthetic intermediates. These compounds are then transformed to previously unknown, higher analogues of the Hajos-Parrish-Eder-Sauer-Wiechert ketone (enone 1, R = Me) following an enantioselective Robinson annulation.

  DOI：

  10.1021/jo800638s