diethyl [(2E,4E)-7-phenylhepta-2,4-dien-1-yl]phosphonate | 1357009-99-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: diethyl [(2E,4E)-7-phenylhepta-2,4-dien-1-yl]phosphonate
• 英文别名: [(3E,5E)-7-[diethoxy(oxido)phosphaniumyl]hepta-3,5-dienyl]benzene
• CAS: 1357009-99-4
• 化学式: C₁₇H₂₅O₃P
• 分子量: 308.357
• InChiKey: XGBIUEDNIJJRJC-DVIJZSFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  41.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  diethyl [(E)-4-bromobut-2-en-1-yl]phosphonate 在 四丁基碘化铵 、 双(三甲基硅烷基)氨基钾 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.41h， 生成 diethyl [(2E,4Z)-7-phenylhepta-2,4-dien-1-yl]phosphonate 、 diethyl [(2E,4E)-7-phenylhepta-2,4-dien-1-yl]phosphonate
  参考文献：
  名称：

  Synthesis of Conjugated Polyenes via Sequential Condensation of Sulfonylphosphonates and Aldehydes

  摘要：

  Selective metalation of sulfonylphosphonates results in sufficiently stable carbanions that undergo chemoselective Julia-Kocienski condensation with various aldehydes to provide (E)-allylic phosphonates in good yields and selectivities. The subsequent Horner-Wadsworth-Emmons condensation with aldehydes is used to synthesize various unsymmetrical trans-dienes, trienes, and tetraenes. This methodology is utilized for the concise synthesis of a naturally occurring fluorescent probe for membrane properties, beta-parinaric acid.

  DOI：

  10.1021/ol203431e

文献信息

• Synthesis of Conjugated Polyenes via Sequential Condensation of Sulfonylphosphonates and Aldehydes
  作者：Nathan R. Cichowicz、Pavel Nagorny

  DOI：10.1021/ol203431e

  日期：2012.2.17

  Selective metalation of sulfonylphosphonates results in sufficiently stable carbanions that undergo chemoselective Julia-Kocienski condensation with various aldehydes to provide (E)-allylic phosphonates in good yields and selectivities. The subsequent Horner-Wadsworth-Emmons condensation with aldehydes is used to synthesize various unsymmetrical trans-dienes, trienes, and tetraenes. This methodology is utilized for the concise synthesis of a naturally occurring fluorescent probe for membrane properties, beta-parinaric acid.