prop-2-enyl (E)-2,5,5-trimethyl-6-oxohex-2-enoate | 241473-97-2

• 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: prop-2-enyl (E)-2,5,5-trimethyl-6-oxohex-2-enoate
• CAS: 241473-97-2
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: XWSQRFWJSNGVDN-UXBLZVDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  prop-2-enyl (E)-2,5,5-trimethyl-6-oxohex-2-enoate 在 samarium diiodide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 以65%的产率得到2-((1R,2R)-2-Hydroxy-3,3-dimethyl-cyclobutyl)-propionic acid allyl ester
  参考文献：
  名称：

  Samarium(II)-mediated 4-exo trig ketyl-olefin cyclisation of unsaturated aldehydes. A general, stereoselective synthesis of functionalised cyclobutanols

  摘要：

  gamma,delta-Unsaturated aldehydes having a quaternary centre in either the a or beta-position, have been prepared from substituted gamma-butyrolactones and undergo efficient 4-exo-trig ketyl-olefin cyclisation on treatment with samarium(II) iodide to give functionalised cyclobutanols. In all cases cyclisation occurs with complete diastereocontrol to give anti-cyclobutanol products. In the cyclisation of substrate 4ab, significant stereochemical control is achieved at three contiguous chiral centres. Both unsaturated esters and vinyl sulfones have been employed as substrates in the reaction. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00910-7
• 作为产物：
  描述：

  4-Hydroxy-2,2-dimethyl-butyraldehyde 在 4 Angstroem MS 、 三氧化硫吡啶 、 二甲基亚砜 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 prop-2-enyl (E)-2,5,5-trimethyl-6-oxohex-2-enoate
  参考文献：
  名称：

  Samarium(II)-mediated 4-exo trig ketyl-olefin cyclisation of unsaturated aldehydes. A general, stereoselective synthesis of functionalised cyclobutanols

  摘要：

  gamma,delta-Unsaturated aldehydes having a quaternary centre in either the a or beta-position, have been prepared from substituted gamma-butyrolactones and undergo efficient 4-exo-trig ketyl-olefin cyclisation on treatment with samarium(II) iodide to give functionalised cyclobutanols. In all cases cyclisation occurs with complete diastereocontrol to give anti-cyclobutanol products. In the cyclisation of substrate 4ab, significant stereochemical control is achieved at three contiguous chiral centres. Both unsaturated esters and vinyl sulfones have been employed as substrates in the reaction. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00910-7