1-cyclohexyl-1-ferrocenemethanol | 12094-90-5

• 分子结构分类: 有机化合物 - 碳氢化合物 - 芳香烃
• 英文名称: 1-cyclohexyl-1-ferrocenemethanol
• 英文别名: (+/-)-α-hydroxy(cyclohexylmethyl)ferrocene；cyclohexyl(cyclopenta-2,4-dien-1-yl)methanol;cyclopenta-1,3-diene;iron(2+)
• CAS: 12094-90-5；185459-02-3；185459-06-7
• 化学式: C₁₇H₂₂FeO
• 分子量: 298.208
• InChiKey: BGHBWPPWUBCICH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  2-羟基-1,4-萘醌 、 1-cyclohexyl-1-ferrocenemethanol 以 水 为溶剂， 反应 24.0h， 以11%的产率得到3-(1-cyclohexyl-1-ferrocenylmethyl)-2-hydroxy-1,4-naphthoquinone
  参考文献：
  名称：

  Synthesis and biological evaluation of novel ferrocene–naphthoquinones as antiplasmodial agents

  摘要：

  This work deals with the synthesis and evaluation of new compounds designed by combination of 1,4naphthoquinone and ferrocene fragments in a 3-ferrocenylmethy1-2-hydroxy-1,4-naphthoquinone arrangement. A practical coupling reaction between 2-hydroxy-1,4-naphthoquinone and ferrocenemethanol derivatives has been developed. This procedure can be carried out "on-water", at moderate temperatures and without auxiliaries or catalysts, with moderate to high yields. The synthesized derivatives have shown significant in vitro antiplasmodial activity against chloroquine-sensitive and resistant Plasmodium falciparum strains and it has been shown that this activity is not related to the inhibition of biomineralization of ferriprotoporphyrin IX. Binding energy calculations and docking of these compounds to cytochrome b in comparison with atovaquone have been performed. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.011
• 作为产物：
  描述：

  cyclohexyl ferrocenylketone 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 反应 0.5h， 生成 1-cyclohexyl-1-ferrocenemethanol
  参考文献：
  名称：

  Synthesis and biological evaluation of novel ferrocene–naphthoquinones as antiplasmodial agents

  摘要：

  This work deals with the synthesis and evaluation of new compounds designed by combination of 1,4naphthoquinone and ferrocene fragments in a 3-ferrocenylmethy1-2-hydroxy-1,4-naphthoquinone arrangement. A practical coupling reaction between 2-hydroxy-1,4-naphthoquinone and ferrocenemethanol derivatives has been developed. This procedure can be carried out "on-water", at moderate temperatures and without auxiliaries or catalysts, with moderate to high yields. The synthesized derivatives have shown significant in vitro antiplasmodial activity against chloroquine-sensitive and resistant Plasmodium falciparum strains and it has been shown that this activity is not related to the inhibition of biomineralization of ferriprotoporphyrin IX. Binding energy calculations and docking of these compounds to cytochrome b in comparison with atovaquone have been performed. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.011

文献信息

• Efficient regio- and diastereo-controlled synthesis of 1,1′- and 1,1′,2,2′-functionalised ferrocenes and the formation of 2-oxa[3]ferrocenophanes
  作者：Michael A. Carroll、Andrew J. P. White、David A. Widdowson、David J. Williams

  DOI：10.1039/b000833h

  日期：——

  A synthesis of a C2 symmetric 1,1′,2,2′-tetrasubstituted ferrocene system is described. The route involves the reduction of ferrocenyl carbonyl compounds which give access to a range of alcohols, alkenes, alkanes, ethers and 2-oxa[3]ferrocenophanes depending on the precise conditions used.

  描述了一种 C2 对称的 1,1'，2,2' 四取代铁烯系统的合成。该路线涉及对铁烯基羰基化合物的还原，根据使用的具体条件，可获得一系列醇、烯烃、烷烃、醚和 2-氧-3-铁烯甙。
• Ortho-lithiation of free ferrocenyl alcohols: a new method for the synthesis of planar chiral ferrocene derivatives
  作者：Bernhard J. Ueberbacher、Herfried Griengl、Hansjörg Weber

  DOI：10.1039/b807895e

  日期：——

  An ortho-metalation method for free ferrocenyl alcohols has been developed, which allows preparation of planar chiral ferrocene derivatives with high yields and diastereoselectivities.

  一种自由铁酚类化合物的邻位金属化方法已经被开发出来，该方法可以高产率和高二面体选择性地制备平面手性的铁烯衍生物。