(3R,4R,5S)-3,5,7-trimethyl-1-octen-4-ol | 618448-77-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4R,5S)-3,5,7-trimethyl-1-octen-4-ol
• 英文别名: (3R,4R,5S)-3,5,7-trimethyloct-1-en-4-ol
• CAS: 618448-77-4
• 化学式: C₁₁H₂₂O
• 分子量: 170.295
• InChiKey: VCJXOUMTYYBVEK-VWYCJHECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3R,4R,5S)-3,5,7-trimethyl-1-octen-4-ol 在 sodium periodate 、 四氧化锇 、 三氟甲磺酸 、 N-甲基吗啉氧化物 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 环己烷 为溶剂， 反应 5.5h， 生成 (2S,3R,4S)-3-Benzyloxy-2,4,6-trimethyl-heptanal
  参考文献：
  名称：

  Asymmetric Synthesis of Four Diastereomers of 3-Hydroxy-2,4,6-trimethylheptanoic Acid:  Proof of Configurational Assignment

  摘要：

  Four unique diastereomers of 3-hydroxy-2,4,6-trimethylheptanoic acid-(2R,3R,4R), (2S,3R,4R), (2S,3R,4S), and (2R,3R,4S)-the fatty acid component of callipeltin A and D, have been synthesized from commercially available (+)- and (-)-pseudoephedrine propionamide in 6 steps and 59% average overall yield. Comparison of the H-1 and C-13 NMR and optical rotation data of the resulting isomers with the natural fragment unambiguously verifies the configurational assignment of the natural isomer as (2R,3R,4R).

  DOI：

  10.1021/jo034738l
• 作为产物：
  描述：

  [1R,2R(S)]-N-(2-hydroxy-1-methyl-2-phenylethyl)-N,2-dimethylpentionamide 在 lithium aluminium tetrahydride 、 三氟化硼乙醚 、 乙酸乙酯 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.0h， 生成 (3R,4R,5S)-3,5,7-trimethyl-1-octen-4-ol
  参考文献：
  名称：

  Asymmetric Synthesis of Four Diastereomers of 3-Hydroxy-2,4,6-trimethylheptanoic Acid:  Proof of Configurational Assignment

  摘要：

  Four unique diastereomers of 3-hydroxy-2,4,6-trimethylheptanoic acid-(2R,3R,4R), (2S,3R,4R), (2S,3R,4S), and (2R,3R,4S)-the fatty acid component of callipeltin A and D, have been synthesized from commercially available (+)- and (-)-pseudoephedrine propionamide in 6 steps and 59% average overall yield. Comparison of the H-1 and C-13 NMR and optical rotation data of the resulting isomers with the natural fragment unambiguously verifies the configurational assignment of the natural isomer as (2R,3R,4R).

  DOI：

  10.1021/jo034738l

文献信息

• Asymmetric Synthesis of Four Diastereomers of 3-Hydroxy-2,4,6-trimethylheptanoic Acid:  Proof of Configurational Assignment
  作者：Jeffrey A. Turk、Gonzalo S. Visbal、Mark A. Lipton

  DOI：10.1021/jo034738l

  日期：2003.10.1

  Four unique diastereomers of 3-hydroxy-2,4,6-trimethylheptanoic acid-(2R,3R,4R), (2S,3R,4R), (2S,3R,4S), and (2R,3R,4S)-the fatty acid component of callipeltin A and D, have been synthesized from commercially available (+)- and (-)-pseudoephedrine propionamide in 6 steps and 59% average overall yield. Comparison of the H-1 and C-13 NMR and optical rotation data of the resulting isomers with the natural fragment unambiguously verifies the configurational assignment of the natural isomer as (2R,3R,4R).