(2S,3S)-3-((E)-hex-1-enyl)-2-methylcyclohexanone | 954143-34-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S)-3-((E)-hex-1-enyl)-2-methylcyclohexanone
• 英文别名: (2S,3S)-3-[(E)-hex-1-enyl]-2-methylcyclohexan-1-one
• CAS: 954143-34-1
• 化学式: C₁₃H₂₂O
• 分子量: 194.317
• InChiKey: LMEKVZMVZYHNBO-TXBNAWBVSA-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：

  (2S,3S)-3-((E)-hex-1-enyl)-2-methylcyclohexanone 、 膦酰基乙酸甲酯二乙酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以98%的产率得到methyl (E)-2-((2S,3S)-3-((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：

  (2S,3S)-3-((E)-hex-1-enyl)-2-methylcyclohexanol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以89%的产率得到(2S,3S)-3-((E)-hex-1-enyl)-2-methylcyclohexanone
  参考文献：
  名称：

  差向异构 (3S)-3-((E)-Hex-1-enyl)-2-甲基环己酮的不对称合成

  摘要：

  不对称铑催化的烯基锆试剂与 2-环己烯酮的 1,4-加成可用于合成 3-烯基-2-甲基环己酮，前提是甲醛用于捕获中间体烯醇锆。以这种方式，开发了导致对映体形式的两个差向异构 3-己烯基-2-甲基环己酮的四步序列。

  DOI：

  10.3390/12020237

文献信息

• Development of Analogues of 1α,25‐Dihydroxyvitamin D ₃ with Biased Side‐Chain Orientation: C20 Methylated Des‐C,D‐homo Analogues
  作者：Freek Vrielynck、Dirk Van Haver、Maurits Vandewalle、Lieve Verlinden、Annemieke Verstuyf、Roger Bouillon、Gianluca Croce、Pierre De Clercq

  DOI：10.1002/ejoc.200801183

  日期：2009.4

  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)
• Asymmetric Synthesis of the Epimeric (3S)-3-((E)-Hex-1-enyl)-2-methylcyclohexanones
  作者：Freek Vrielynck、Pierre De Clercq

  DOI：10.3390/12020237

  日期：——

  asymmetric rhodium-catalysed 1,4-addition of alkenylzirconium reagents to 2-cyclohexenone can be useful in the synthesis of 3-alkenyl-2-methylcyclohexanones, provided that formaldehyde is used in trapping the intermediate zirconium enolates. In this manner a four-step sequence leading to the two epimeric 3-hexenyl-2-methylcyclohexanones in enantiomeric form was developed.

  不对称铑催化的烯基锆试剂与 2-环己烯酮的 1,4-加成可用于合成 3-烯基-2-甲基环己酮，前提是甲醛用于捕获中间体烯醇锆。以这种方式，开发了导致对映体形式的两个差向异构 3-己烯基-2-甲基环己酮的四步序列。