((3-carbomethoxy)propyl)ferrocene | 33637-67-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ((3-carbomethoxy)propyl)ferrocene
• 英文别名: methyl ester of 4-ferrocenylbutanoic acid；3-methoxycarbonylpropylferrocene
• CAS: 33637-67-1
• 化学式: C₁₅H₁₈FeO₂
• 分子量: 286.154
• InChiKey: OHCQZDOPPUMPJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.29
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ((3-carbomethoxy)propyl)ferrocene 、 lithium aluminium tetrahydride 以 乙醚 为溶剂， 以93%的产率得到4-ferrocenylbutanol
  参考文献：
  名称：

  Synthesis and electrochemical properties of a series of ferrocene-containing alcohols

  摘要：

  A series of primary ferrocenylalcohols, Fc-(CH2)(m)-OH with m = 1-4 and Fc = ferrocenyl, was synthesised by reduction of the appropriate ferrocenylcarboxylic acids, Fc - (CH2)(n)- COOH (n = 0-3) and the ester methyl 4-ferrocenylbutanoate with LiAIH(4), the reduction of the gamma-ketoacid ferrocylpropanoic acid, Fc-CO-(CH2)(2)-COOH, with AlCl3/LiAlH4, and the reduction of ferrocenylcarboxaldehyde, FcCHO, with NaBH4. The secondary ferrocenyl alcohols CpFe(C5H4-CH(OH)-CH3) and Fe(C5H4-CH(OH)-CH3)(2) were obtained by NaBH4 reduction of acetyl and diacetyl ferrocene. The different reduction methods are compared. The electrochemistry of the alcohols was studied by cyclic voltarnmetry in CH3CN/0.1 M N("BU)(4)PF6 utilising a platinum working electrode. The ferrocenyl group showed reversible electrochemistry with the formal reduction potential (E-o ' versus Fc/Fc(+)) of the ferrocenyl group inversely proportional to side chain length. The influence of the side chain length on E-O ' was more pronounced for the acids because the electron-withdrawing properties of the carbonyl group is stronger than that of the alcohol group. Ion pairing was found to play a major role in the electrochemical behaviour of ferrocenylmethanol, Fc-CH2-OH. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2005.04.022
• 作为产物：
  描述：

  {3-(methoxycarbonyl) propanoyl} ferrocene 在 sodium tetrahydroborate 作用下， 以 二氯甲烷 、 三氟乙酸 为溶剂， 以88%的产率得到((3-carbomethoxy)propyl)ferrocene
  参考文献：
  名称：

  Simple reduction of ferrocenyl aldehydes and ketones by sodium boranuide in trifluoroacetic acid: new, efficient, general preparation of alkylferrocenes

  摘要：

  通过使用硼氢化钠和三氟乙酸，对二茂铁基醛和酮进行离子氢化反应，可以以极佳的产率获得烷基二茂铁化合物。

  DOI：

  10.1039/p19960001381

文献信息

• Ionic Hydrogenation of Acylferrocenes Using Zinc Borohydride:  An Efficient, Mild Method for the Preparation of Alkylferrocenes
  作者：Sukanta Bhattacharyya

  DOI：10.1021/om950751n

  日期：1996.2.6

  An effective mild procedure for the reductive deoxygenation of α-ferrocenyl aldehydes, ketones, and alcohols into the corresponding alkylferrocenes is described using a combination of zinc borohydride and zinc chloride. This is the first example of such reactivity of zinc borohydride. The present method allows the synthesis of alkylferrocenes bearing terminally functionalized pendant chains.

  描述了使用硼氢化锌和氯化锌的组合将α-二茂铁基醛，酮和醇还原脱氧为相应的烷基二茂铁的有效温和程序。这是硼氢化锌的这种反应性的第一个例子。本方法允许合成带有末端官能化的侧链的烷基二茂铁。
• Bhattacharyya, Sukanta, Journal of the Chemical Society, Dalton Transactions, 1996, p. 4617 - 4620
  作者：Bhattacharyya, Sukanta

  DOI：——

  日期：——