methyl 4-(4-hydroxy-5-methylhexyl)benzoate | 615581-21-0

• 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: methyl 4-(4-hydroxy-5-methylhexyl)benzoate
• CAS: 615581-21-0
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: LOURRSGKMICTOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 4-(4-hydroxy-5-methylhexyl)benzoate 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以75%的产率得到methyl 4-(5-methyl-4-oxohexyl)benzoate
  参考文献：
  名称：

  Samarium(II)-Promoted Radical Spirocyclization onto an Aromatic Ring

  摘要：

  Samarium(II)-mediated spirocyclization onto an aromatic ring was achieved by the reaction of methyl 4-(4-oxoalkyl)benzoates with SmI2 in the presence of i-PrOH and HMPA, yielding methyl 1-alkyl-1-hydroxyspiro[4.5]dec-6-ene-8-carboxylates in moderate to high yields. Utilizing this chemistry, spiro[3.5] and -[5.5] systems, and sterically congested spiro[4.5] systems, were easily synthesized. For the successful conversion, appropriate activation of the aromatic ring has proven to be extremely important: while an ester or amide functionality on the aromatic ring can promote the spirocyclization, a sulfonamide substituent causes ortho cyclization.

  DOI：

  10.1021/jo034767w
• 作为产物：
  描述：

  2-(1,3-二氧戊环-2-基)乙基三苯基溴化磷 在 palladium on activated charcoal 氢气 、 4-甲基苯磺酸吡啶 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 水 、 丙酮 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 14.0h， 生成 methyl 4-(4-hydroxy-5-methylhexyl)benzoate
  参考文献：
  名称：

  Samarium(II)-Promoted Radical Spirocyclization onto an Aromatic Ring

  摘要：

  Samarium(II)-mediated spirocyclization onto an aromatic ring was achieved by the reaction of methyl 4-(4-oxoalkyl)benzoates with SmI2 in the presence of i-PrOH and HMPA, yielding methyl 1-alkyl-1-hydroxyspiro[4.5]dec-6-ene-8-carboxylates in moderate to high yields. Utilizing this chemistry, spiro[3.5] and -[5.5] systems, and sterically congested spiro[4.5] systems, were easily synthesized. For the successful conversion, appropriate activation of the aromatic ring has proven to be extremely important: while an ester or amide functionality on the aromatic ring can promote the spirocyclization, a sulfonamide substituent causes ortho cyclization.

  DOI：

  10.1021/jo034767w

文献信息

• Samarium(II)-Promoted Radical Spirocyclization onto an Aromatic Ring
  作者：Hiroaki Ohno、Mitsuaki Okumura、Shin-ichiro Maeda、Hiroki Iwasaki、Ryutaro Wakayama、Tetsuaki Tanaka

  DOI：10.1021/jo034767w

  日期：2003.10.1

  Samarium(II)-mediated spirocyclization onto an aromatic ring was achieved by the reaction of methyl 4-(4-oxoalkyl)benzoates with SmI2 in the presence of i-PrOH and HMPA, yielding methyl 1-alkyl-1-hydroxyspiro[4.5]dec-6-ene-8-carboxylates in moderate to high yields. Utilizing this chemistry, spiro[3.5] and -[5.5] systems, and sterically congested spiro[4.5] systems, were easily synthesized. For the successful conversion, appropriate activation of the aromatic ring has proven to be extremely important: while an ester or amide functionality on the aromatic ring can promote the spirocyclization, a sulfonamide substituent causes ortho cyclization.