methyl (2S,4S,6R)-2,4,6-trimethyl-7-oxoheptanoate | 808109-22-0

• 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)-2,4,6-trimethyl-7-oxoheptanoate
• CAS: 808109-22-0
• 化学式: C₁₁H₂₀O₃
• 分子量: 200.278
• InChiKey: DKLCAJGLAGLKMM-AEJSXWLSSA-N

物化性质

• 沸点：
  251.6±23.0 °C(Predicted)
• 密度：
  0.944±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (2S,4S,6R)-2,4,6-trimethyl-7-oxoheptanoate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以65%的产率得到
  参考文献：
  名称：

  Asymmetric Synthesis of Deoxypolypropionate Units via Stereoselective Hydrogenation of Optically Active Cycloheptatriene

  摘要：

  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.

  DOI：

  10.1021/ol0483596
• 作为产物：
  描述：

  acetic acid 12-hydroxy-2,4,9,11-tetramethyl-1,5-dioxa-spiro[5.6]dodeca-8,10-dien-7-ylmethyl ester 在 镍 lead(IV) acetate 、 lithium aluminium tetrahydride 、 氢气 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 44.59h， 生成 methyl (2S,4S,6R)-2,4,6-trimethyl-7-oxoheptanoate
  参考文献：
  名称：

  Asymmetric Synthesis of Deoxypolypropionate Units via Stereoselective Hydrogenation of Optically Active Cycloheptatriene

  摘要：

  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.

  DOI：

  10.1021/ol0483596

文献信息

• 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.
• 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.