(Z)-1-cyclopropyl-2-(hydroxy(phenyl)methyl)hept-2-en-1-one

• 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: (Z)-1-cyclopropyl-2-(hydroxy(phenyl)methyl)hept-2-en-1-one
• 英文别名: (Z)-1-cyclopropyl-2-[hydroxy(phenyl)methyl]hept-2-en-1-one
• 化学式: C₁₇H₂₂O₂
• 分子量: 258.36
• InChiKey: XMOIKWVJDKQLRG-GDNBJRDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  、 苯甲醛 在 scandium tris(trifluoromethanesulfonate) 盐酸 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 生成 (Z)-1-cyclopropyl-2-(hydroxy(phenyl)methyl)hept-2-en-1-one 、 (E)-1-cyclopropyl-2-(hydroxy(phenyl)methyl)hept-2-en-1-one
  参考文献：
  名称：

  Stereoselective Lewis Acid-Catalyzed α-Acylvinyl Additions

  摘要：

  Silyloxyallenes derived from alpha-hydroxypropargylsilanes undergo efficient addition to aldehydes with catalytic amounts of Lewis acids. The allenes are accessed from the corresponding propargylsilanes in a base-catalyzed 1,2-Brook rearrangement/SE2' process. Enantioenriched propargylsilanes are synthesized by a new zinc-promoted addition of alkynes to acylsilanes in up to 74% ee. This work demonstrates that conversion to the silyloxyallenes occurs with minimal erosion in optical activity. The use of a chiral chromium(III) Lewis acid effects the catalytic asymmetric addition of racemic silyloxyallenes to aromatic aldehydes in up to 92% ee. The overall reaction is broad in scope and accommodates a wide variety of aromatic and aliphatic substituents on both the propargylsilane and aldehyde.

  DOI：

  10.1021/ja0653674