(2S,5R)-5-[(E)-hex-1-enyl]-2-methylcyclohexanone | 1160371-34-5

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机氧化物
• 英文名称: (2S,5R)-5-[(E)-hex-1-enyl]-2-methylcyclohexanone
• 英文别名: (2S,5R)-5-[(E)-hex-1-enyl]-2-methylcyclohexan-1-one
• CAS: 1160371-34-5
• 化学式: C₁₃H₂₂O
• 分子量: 194.317
• InChiKey: UXOFBNQVXPOFPX-FNSAGKMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (三甲基硅基)乙酸甲酯 、 (2S,5R)-5-[(E)-hex-1-enyl]-2-methylcyclohexanone 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 生成 methyl (Z)-2-((2S,5R)-5-((E)-hex-1-en-1-yl)-2-methylcyclohexylidene)acetate 、 methyl (E)-2-((2S,5R)-5-((E)-hex-1-en-1-yl)-2-methylcyclohexylidene)acetate
  参考文献：
  名称：

  Development of Analogues of 1α,25‐Dihydroxyvitamin D ₃ with Biased Side‐Chain Orientation: C20 Methylated Des‐C,D‐homo Analogues

  摘要：

  AbstractThe discovery that 1α,25‐dihydroxyvitamin D3 is effective in the inhibition of cellular proliferation and in the induction of cellular differentiation has led to a search for analogues in which these activities and the classical calcemic activity of the hormone are dissociated. In this context, the synthesis and biological evaluation are reported for six CD‐ring modified structural analogues that were conceived so as to enforce a particular orientation of the 25‐hydroxylated side chain. The analogues are characterized by the absence of the C‐ring and the presence of an unnatural six‐membered D‐ring. The biased side‐chain orientations are realized through the stereocontrolled incorporation of methyl substituents at positions C13/C20 and C16/C20. Comparison of the results of the biological evaluation and conformational analysis of the side chain confirms the existence of a relationship between inhibition of MCF‐7 breast cancer cell proliferation and side chain geometry.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  DOI：

  10.1002/ejoc.200801183
• 作为产物：
  描述：

  6-methylcyclohex-2-en-1-one 、 1-己炔 在 Schwartz's reagent 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 作用下， 以 四氢呋喃 为溶剂， 反应 4.25h， 生成 (2R,5R)-5-[(E)-hex-1-enyl]-2-methylcyclohexanone 、 (2S,5R)-5-[(E)-hex-1-enyl]-2-methylcyclohexanone
  参考文献：
  名称：

  Development of Analogues of 1α,25‐Dihydroxyvitamin D ₃ with Biased Side‐Chain Orientation: C20 Methylated Des‐C,D‐homo Analogues

  摘要：

  AbstractThe discovery that 1α,25‐dihydroxyvitamin D3 is effective in the inhibition of cellular proliferation and in the induction of cellular differentiation has led to a search for analogues in which these activities and the classical calcemic activity of the hormone are dissociated. In this context, the synthesis and biological evaluation are reported for six CD‐ring modified structural analogues that were conceived so as to enforce a particular orientation of the 25‐hydroxylated side chain. The analogues are characterized by the absence of the C‐ring and the presence of an unnatural six‐membered D‐ring. The biased side‐chain orientations are realized through the stereocontrolled incorporation of methyl substituents at positions C13/C20 and C16/C20. Comparison of the results of the biological evaluation and conformational analysis of the side chain confirms the existence of a relationship between inhibition of MCF‐7 breast cancer cell proliferation and side chain geometry.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  DOI：

  10.1002/ejoc.200801183