(Sp)-(2-pyridylmethyl)ferroceno[d]pyridazin-4(3H)-one | 1296753-24-6

• 英文名称: (Sp)-(2-pyridylmethyl)ferroceno[d]pyridazin-4(3H)-one
• CAS: 1296753-24-6
• 化学式: C₁₈H₁₅FeN₃O
• 分子量: 345.184
• InChiKey: MVFXLKNSVDMBDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
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• 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：
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反应信息

• 作为产物：
  描述：

  (Sp)-ferroceno[d]pyridazin-4(3H)-one 、 2-(溴甲基)吡啶氢溴酸盐 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以64%的产率得到(Sp)-(2-pyridylmethyl)ferroceno[d]pyridazin-4(3H)-one
  参考文献：
  名称：

  Synthesis and structure of planar chiral ferroceno[d]pyridazinones, the first representatives of a novel class of fused metallocenes

  摘要：

  A series of planar chiral ferroceno[d]pyridazinones was prepared by hydrazine-mediated cyclisations of (Sp)-2-formylferrocenoyl fluoride obtained in two steps from (2S,4S)-4-(methoxymethyl)-2-ferrocenyl-1,3-dioxane. Further derivatives based on the novel heterocyclic scaffold were resulted by means of the facile N-alkylation reactions carried out on the easily accessible fused product derived from the hydrazine-mediated cyclisation. Upon treatment with hydrazine (Sp)-2-formylferroce carboxylic acid, the precursor of the acid fluoride with enhanced reactivity, afforded a dimeric azine avoiding cyclisation. The spectacular difference between the experimentally observed reactivity of the bifunctional formyl-ferrocenes was disclosed by comparative DFT analysis of the assumed hydrazone-and hydrazide intermediates with different values of LUMO energy associated with different conformation. The structures of the new compounds were established by IR and NMR spectroscopy, including HMQC, HMBC and DNOE measurements. (C) 2011 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2011.01.032