(3S,4S,E)-6-cyclohexyl-2,4-dimethylhexa-1,5-dien-3-ol | 1017246-19-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,4S,E)-6-cyclohexyl-2,4-dimethylhexa-1,5-dien-3-ol
• 英文别名: (3S,4S,5E)-6-cyclohexyl-2,4-dimethylhexa-1,5-dien-3-ol
• CAS: 1017246-19-3
• 化学式: C₁₄H₂₄O
• 分子量: 208.344
• InChiKey: AXZXDXSVYGCCDP-JMRXXTBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  (3S,4S,E)-6-cyclohexyl-2,4-dimethylhexa-1,5-dien-3-ol 、 碘甲烷 在 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以93%的产率得到((3S,4S,E)-4-methoxy-3,5-dimethylhexa-1,5-dienyl)cyclohexane
  参考文献：
  名称：

  Asymmetric Catalysis Route to anti,anti Stereotriads, Illustrated by Applications

  摘要：

  A short sequence based on asymmetric catalysis, chirality transfer, and an optimized carbometallation protocol gave an anti,anti stereotriad building block in six steps. Both enantiomers of the chirality source, N-methyl ephedrine, are inexpensive, and the auxiliary is recoverable. In one chiral series, the building block was converted to the "B-2" intermediate in Miyashita's synthesis of scytophycin C; in the enantiomeric series, it was converted to a key intermediate for aplyronine A and to the polyketide "cap" for the callipeltins.

  DOI：

  10.1021/ol702989g
• 作为产物：
  描述：

  (Z,S)-α-(1-Propenyl)cyclohexanemethanol 在 正丁基锂 、 potassium tert-butylate 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 生成 (3S,4S,E)-6-cyclohexyl-2,4-dimethylhexa-1,5-dien-3-ol
  参考文献：
  名称：

  Scalable, Catalytic Asymmetric Synthesis of Syn, Anti Stereotriad Building Blocks for Polypropionate Antibiotics

  摘要：

  Asymmetric catalysis and chirality transfer by the 2,3-Wittig rearrangement were combined to provide a syn, anti stereotriad-containing olefinic alcohol in five steps from inexpensive starting materials. Development of this compound, a versatile intermediate for polypropionate synthesis, gave known building blocks for discodermolide.

  DOI：

  10.1021/ol0612612