Toluene-4-sulfonic acid (2S,3R,4S)-3-hydroxy-2,4-dimethyl-heptyl ester | 115047-17-1

• 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: Toluene-4-sulfonic acid (2S,3R,4S)-3-hydroxy-2,4-dimethyl-heptyl ester
• CAS: 115047-17-1
• 化学式: C₁₆H₂₆O₄S
• 分子量: 314.446
• InChiKey: OFRZLQUJKBNTSG-OFQRWUPVSA-N

物化性质

• 沸点：
  450.5±28.0 °C(predicted)
• 密度：
  1.105±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 重原子数：
  21.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Toluene-4-sulfonic acid (2S,3R,4S)-3-hydroxy-2,4-dimethyl-heptyl ester 在 4-二甲氨基吡啶 、 三乙胺 、 sodium iodide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 3.5h， 生成 (2SR,3SR,4RS)-1-iodo-2,4-dimethyl-3-O-propionyl-3-heptanol
  参考文献：
  名称：

  Stereoselective total synthesis of (.+-.)-invictolide. An efficient preparation of a trisubstituted .delta.-lactone from aldol precursors

  摘要：

  The stereoselective total synthesis of (+/-)-invictolide (1), a component of the queen recognition pheromone of Solenopsis invicta, is described. The TiCl4-mediated addition of silyl ketene thioacetal 8 to (+/-)-3-(benzyloxy)-2-methylpropionaldehyde afforded exclusively thioester 10, in 65% yield, which was straightforwardly converted to diol 5 (ca. 31% yield). Diol 5 was also prepared after LiAlH4 reduction of the major aldol formed in the condensation between the lithium enolate of 2,6-di-tert-butyl-4-methylphenyl propanoate and (+/-)-2-methylvaleraldehyde (ca.50% overall yield). Intramolecular alkylation (t-BuOK-THF) of 6 or 7 gave a 40:60 mixture of (+/-)-1 and its C(3) epimer. Catalytic hydrogenation of unsaturated lactone 17 afforded (+/-)-1 in 80% yield.

  DOI：

  10.1021/jo00054a014
• 作为产物：
  描述：

  2-甲基戊醛 在 lithium aluminium tetrahydride 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 23.83h， 生成 Toluene-4-sulfonic acid (2S,3R,4S)-3-hydroxy-2,4-dimethyl-heptyl ester
  参考文献：
  名称：

  Stereoselective total synthesis of (.+-.)-invictolide. An efficient preparation of a trisubstituted .delta.-lactone from aldol precursors

  摘要：

  The stereoselective total synthesis of (+/-)-invictolide (1), a component of the queen recognition pheromone of Solenopsis invicta, is described. The TiCl4-mediated addition of silyl ketene thioacetal 8 to (+/-)-3-(benzyloxy)-2-methylpropionaldehyde afforded exclusively thioester 10, in 65% yield, which was straightforwardly converted to diol 5 (ca. 31% yield). Diol 5 was also prepared after LiAlH4 reduction of the major aldol formed in the condensation between the lithium enolate of 2,6-di-tert-butyl-4-methylphenyl propanoate and (+/-)-2-methylvaleraldehyde (ca.50% overall yield). Intramolecular alkylation (t-BuOK-THF) of 6 or 7 gave a 40:60 mixture of (+/-)-1 and its C(3) epimer. Catalytic hydrogenation of unsaturated lactone 17 afforded (+/-)-1 in 80% yield.

  DOI：

  10.1021/jo00054a014

文献信息

• Applications of the 3-methyl-.gamma.-butyrolactone strategy to the synthesis of polypropionates: the Prelog-Djerassi lactonic ester, ent-invictolide, and the C19-C27 fragment of rifamycin S
  作者：Frederick E. Ziegler、William T. Cain、Alyssa. Kneisley、Eugene P. Stirchak、Ronald T. Wester

  DOI：10.1021/ja00224a032

  日期：1988.8
• R-3-methyl-γ-butyrolactone as a template for the synthesis of (+)-invictolide
  作者：Frederick E. Ziegler、Eugene P. Stirchak、Ronald T. Wester

  DOI：10.1016/s0040-4039(00)84224-0

  日期：——