methyl (2S,4S,6R)-7-hydroxy-2,4,6-trimethylheptanoate | 863991-51-9

• 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: methyl (2S,4S,6R)-7-hydroxy-2,4,6-trimethylheptanoate
• CAS: 863991-51-9
• 化学式: C₁₁H₂₂O₃
• 分子量: 202.294
• InChiKey: DIJRKXFVWZAAFL-AEJSXWLSSA-N

物化性质

• 沸点：
  260.2±23.0 °C(Predicted)
• 密度：
  0.953±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 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 (2S,4S,6R)-7-hydroxy-2,4,6-trimethylheptanoate 在 咪唑 、 dilithium tetrachlorocuprate 、 水 、 碘 、 二异丁基氢化铝 、 三乙胺 、 三苯基膦 、 lithium hydroxide 、 双环己基(三氟甲烷磺酰氧基)硼烷 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 31.75h， 生成 (2R,3R,4S,6S,8S)-3-hydroxy-2,4,6,8,10-pentamethylundecanoic acid
  参考文献：
  名称：

  A non-iterative, flexible, and highly stereoselective synthesis of polydeoxypropionates—synthesis of (+)-vittatalactone

  摘要：

  一个简短的反应序列，包括氧-科普重排、铱催化氢化和烯醇盐甲基化，提供了具有出色的非对映选择性的三脱氧丙酸酯。黄瓜甲虫信息素（+）-维塔酮的简单合成展示了这一新策略。

  DOI：

  10.1039/c0cc05215a
• 作为产物：
  描述：

  (2S,3R,5S,7S)-2-hydroxy-3,5,7-trimethylcycloheptan-1-one 在 lead(IV) acetate 、 sodium tetrahydroborate 作用下， 以 甲醇 、 苯 为溶剂， 反应 2.17h， 生成 methyl (2S,4S,6R)-7-hydroxy-2,4,6-trimethylheptanoate
  参考文献：
  名称：

  Stereoselective hydrogenation of conjugate diene directed by hydroxy group and asymmetric synthesis of deoxypolypropionate units

  摘要：

  Optically active cyclic compounds carrying a conjugate diene and two hydroxy groups were prepared through the intramolecular Buchner reaction with a chiral tether and succeeding stereoselective conversion. Hydrogenation of the diene in the first step was not regio-selective but resulted in three regioisomeric monoenes. Nevertheless. the final saturated product carrying two stereogenic centers could be obtained in 98% stereochemical purity on further hydrogenation under optimized conditions. The high stereoselectivity throughout the multiple pathways is attributable to the effective direction by the hydroxy group. Ring cleavage of the produced stereochemically pure seven-membered ring compounds successfully resulted in synthetic intermediates for deoxypolypropionates. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.128

文献信息

• A General, Asymmetric, and Noniterative Synthesis of Trideoxypropionates. Straightforward Syntheses of the Pheromones (+)-Vittatalactone and (+)-Norvittatalactone
  作者：Christian F. Weise、Matthias C. Pischl、Andreas Pfaltz、Christoph Schneider

  DOI：10.1021/jo202330b

  日期：2012.2.3

  A novel, highly stereocontrolled, and very flexible synthetic access to biologically relevant trideoxypropionate building blocks in optically pure form has been developed. On the basis of a three-step sequence comprising a thermal oxy-Cope rearrangement, an iridium-catalyzed hydrogenation, and an auxiliary-controlled enolate methylation, trideoxypropionates with easily adjustable relative configuration were synthesized in excellent yields. In addition, the functionalized end groups allow for chemoselective manipulations and further elongation of the chain. The underlying strategy constitutes the first noniterative process for the assembly of polydeoxypropionates and has further been applied in total syntheses of the pheromones (+)-vittatalactone and (+)-norvittatalactone, which had been isolated from the striped cucumber beetle Acalymma vittatum.
• Asymmetric Synthesis of Deoxypolypropionate Units via Stereoselective Hydrogenation of Optically Active Cycloheptatriene
  作者：Takashi Sugimura、Yasuhiro Sato、Chun Young Im、Tadashi Okuyama

  DOI：10.1021/ol0483596

  日期：2004.11.1

  Optically active polypropionate units were synthesized in 9-11 steps from 3,5-dimethylphenol. The sequence consists of the BUchner reaction controlled by a chiral 2,4-pentanediol tether and diastereoselective hydrogenation over Raney nickel.
• A non-iterative, flexible, and highly stereoselective synthesis of polydeoxypropionates—synthesis of (+)-vittatalactone
  作者：Christian F. Weise、Matthias Pischl、Andreas Pfaltz、Christoph Schneider

  DOI：10.1039/c0cc05215a

  日期：——

  A short sequence comprising an oxy-Cope rearrangement, iridium-catalyzed hydrogenation, and enolate methylation provides trideoxypropionates with excellent diastereocontrol. A straightforward synthesis of the cucumber beetle pheromone (+)-vittatalactone illustrates this new strategy.

  一个简短的反应序列，包括氧-科普重排、铱催化氢化和烯醇盐甲基化，提供了具有出色的非对映选择性的三脱氧丙酸酯。黄瓜甲虫信息素（+）-维塔酮的简单合成展示了这一新策略。
• Stereoselective hydrogenation of conjugate diene directed by hydroxy group and asymmetric synthesis of deoxypolypropionate units
  作者：Takashi Sugimura、Chun Young Im、Yasuhiro Sato、Tadashi Okuyama

  DOI：10.1016/j.tet.2007.02.128

  日期：2007.5

  Optically active cyclic compounds carrying a conjugate diene and two hydroxy groups were prepared through the intramolecular Buchner reaction with a chiral tether and succeeding stereoselective conversion. Hydrogenation of the diene in the first step was not regio-selective but resulted in three regioisomeric monoenes. Nevertheless. the final saturated product carrying two stereogenic centers could be obtained in 98% stereochemical purity on further hydrogenation under optimized conditions. The high stereoselectivity throughout the multiple pathways is attributable to the effective direction by the hydroxy group. Ring cleavage of the produced stereochemically pure seven-membered ring compounds successfully resulted in synthetic intermediates for deoxypolypropionates. (C) 2007 Elsevier Ltd. All rights reserved.