(3S,1E)-dimethyl[3-(p-tolyl)-1-butenyl]phosphonate | 637025-08-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (3S,1E)-dimethyl[3-(p-tolyl)-1-butenyl]phosphonate
• 英文别名: 1-[(E,2S)-4-dimethoxyphosphorylbut-3-en-2-yl]-4-methylbenzene
• CAS: 637025-08-2
• 化学式: C₁₃H₁₉O₃P
• 分子量: 254.266
• InChiKey: QEYDPIRSVRFCFA-VMPCVLLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,1E)-dimethyl[3-(p-tolyl)-1-butenyl]phosphonate 在 硼烷四氢呋喃络合物 、 双氧水 、 sodium acetate 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.0h， 生成 (R)-3-(p-tolyl)butanal 、 (S)-3-(p-tolyl)butanal
  参考文献：
  名称：

  Stereospecific Pd(0)-Catalyzed Arylation of an Allylic Hydroxy Phosphonate Derivative:  Formal Synthesis of (S)-(+)-ar-Turmerone

  摘要：

  Reaction of the (1S)-allylic hydroxy phosphonate 1(S) with methyl chloroformate in pyridine yields the corresponding carbonate 3(S). The carbonate 3(S) undergoes a palladium-catalyzed arylation with p-tolyl tributylstannane to give both the 1E and 1Z vinyl phosphonates 6 (85:15). The E and Z vinyl phosphonates 6 were shown to have the opposite configuration at C-3. The major vinyl phosphonate isomer (3S,1E), was converted to (3S)-3-(p-tolyl)-butanal 8(S), completing a formal total synthesis of (S)-ar-turmerone 5a.

  DOI：

  10.1021/jo0351318
• 作为产物：
  描述：

  (1S,2E)-dimethyl(1-hydroxy-2-butenyl)phosphonate 在 吡啶 、 N-甲基吡咯烷酮 、 4-二甲氨基吡啶 、 tris(dibenzylideneacetone)dipalladium (0) 、 三(2-呋喃基)膦 作用下， 以 乙腈 为溶剂， 反应 5.0h， 生成 (3S,1E)-dimethyl[3-(p-tolyl)-1-butenyl]phosphonate
  参考文献：
  名称：

  Stereospecific Pd(0)-Catalyzed Arylation of an Allylic Hydroxy Phosphonate Derivative:  Formal Synthesis of (S)-(+)-ar-Turmerone

  摘要：

  Reaction of the (1S)-allylic hydroxy phosphonate 1(S) with methyl chloroformate in pyridine yields the corresponding carbonate 3(S). The carbonate 3(S) undergoes a palladium-catalyzed arylation with p-tolyl tributylstannane to give both the 1E and 1Z vinyl phosphonates 6 (85:15). The E and Z vinyl phosphonates 6 were shown to have the opposite configuration at C-3. The major vinyl phosphonate isomer (3S,1E), was converted to (3S)-3-(p-tolyl)-butanal 8(S), completing a formal total synthesis of (S)-ar-turmerone 5a.

  DOI：

  10.1021/jo0351318

文献信息

• Stereospecific Pd(0)-Catalyzed Arylation of an Allylic Hydroxy Phosphonate Derivative:  Formal Synthesis of (<i>S</i>)-(+)-ar-Turmerone
  作者：Bradley J. Rowe、Christopher D. Spilling

  DOI：10.1021/jo0351318

  日期：2003.11.1

  Reaction of the (1S)-allylic hydroxy phosphonate 1(S) with methyl chloroformate in pyridine yields the corresponding carbonate 3(S). The carbonate 3(S) undergoes a palladium-catalyzed arylation with p-tolyl tributylstannane to give both the 1E and 1Z vinyl phosphonates 6 (85:15). The E and Z vinyl phosphonates 6 were shown to have the opposite configuration at C-3. The major vinyl phosphonate isomer (3S,1E), was converted to (3S)-3-(p-tolyl)-butanal 8(S), completing a formal total synthesis of (S)-ar-turmerone 5a.