ethyl (3S,4R)-4-formyl-2-methylidene-3-phenylhexanoate | 1332507-19-3

• 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: ethyl (3S,4R)-4-formyl-2-methylidene-3-phenylhexanoate
• CAS: 1332507-19-3
• 化学式: C₁₆H₂₀O₃
• 分子量: 260.333
• InChiKey: ADHRLCBMPPEYLS-ZFWWWQNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl 2-(bromomethyl)-3-phenylacrylate 在 (L)-2-{diphenyl[(triphenylsilyl)oxy]methyl}pyrrolidine 作用下， 以 二氯甲烷 为溶剂， 反应 48.5h， 生成 ethyl (3S,4R)-4-formyl-2-methylidene-3-phenylhexanoate 、
  参考文献：
  名称：

  Enantio- and Diastereoselective Organocatalytic α-Alkylation of Aldehydes with 3-Substituted 2-(Bromomethyl)acrylates

  摘要：

  The catalytic direct alpha-alkylation of aldehydes with 2-(bromomethyl)acrylates has been accomplished, giving rise to alpha-branched and functionalized aldehydes of high diastereo- and enantiopurity. The influence of the nature of the ester group of the acrylates in reaction stereoselectivity and especially in reactivity is investigated. Optimum conditions implicate the use of phenyl acrylates in conjunction with organocatalyst 8. Application of thus obtained adducts in synthesis is illustrated with a concise stereocontrolled preparation of trisubstituted cyclopentenes.

  DOI：

  10.1021/jo202073n