rac-1,3-diferrocenylprop-2-en-1-ol | 72971-83-6

• 英文名称: rac-1,3-diferrocenylprop-2-en-1-ol
• 英文别名: 1,3-diferrocenylprop-1-ene-3-ol
• CAS: 72971-83-6
• 化学式: C₂₃H₂₂Fe₂O
• 分子量: 426.121
• InChiKey: IFRQDNBEWFMYSA-AHJYMZSGSA-N

计算性质

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

反应信息

• 作为反应物：
  描述：

  rac-1,3-diferrocenylprop-2-en-1-ol 在 tetrafluoroboric acid 、 potassium thioacyanate 作用下， 以 二氯甲烷 、 水 为溶剂， 以64%的产率得到1,3-diferrocenyl-1-isothiocyanato-2-propene
  参考文献：
  名称：

  Boev, V. I.; Dombrovskii, A. V., Journal of general chemistry of the USSR, 1985, vol. 55, p. 1045 - 1048

  摘要：

  DOI：
• 作为产物：
  描述：

  1,3-diferrocenyl-2-propen-1-one 、 sodium tetrahydroborate 以 1,4-二氧六环 、 甲醇 为溶剂， 以100%的产率得到rac-1,3-diferrocenylprop-2-en-1-ol
  参考文献：
  名称：

  Boev, V. I.; Dombrovskii, A. V., Journal of general chemistry of the USSR, 1985, vol. 55, p. 1045 - 1048

  摘要：

  DOI：

文献信息

• Metallocene-Terminated Allylium Salts:  The Effect of End Group on Localization in Polymethines
  作者：Stephen Barlow、Lawrence M. Henling、Michael W. Day、William P. Schaefer、Jennifer C. Green、Tony Hascall、Seth R. Marder

  DOI：10.1021/ja012472z

  日期：2002.6.1

  synthesized by anion metathesis from the corresponding PF(6) salts. The crystal structure of [Fc' '(CH)(3)Fc' '](+)[PF(6)](-) contains symmetrical termethine cations, while the same appears to be true in the disordered structure of [Fc(CH)(3)Fc](+)[PF(6)](-). The formally unsymmetrical cation in [Fc(CH)(3)Fc' '](+)[BF(4)](-) is only slightly unsymmetrical with little bond-length alternation in the allylium

  一系列 1,3-二(茂金属)烯丙基盐 [Mc(CH)(3)Mc'](+)[X](-) [Mc, Mc' = 二茂铁 (Fc), 2,3,4, 5,1',2',3',4'-octamethylferrocen-1-yl (Fc''), ruthenocenyl (Rc); X = BF(4), PF(6)] 是通过（2-锂硫乙烯基）茂金属与甲酰基茂金属反应合成的，然后用 HX 处理得到的醇。X = BAr'(4) [Ar' = 3,5-(CF(3))(2)C(6)H(3)] 的两种盐是由相应的 PF(6) 盐的阴离子复分解合成的。[Fc' '(CH)(3)Fc' '](+)[PF(6)](-) 的晶体结构包含对称的 Termethine 阳离子，而 [Fc( CH)(3)Fc](+)[PF(6)](-)。[Fc(CH)(3)Fc' ' 中形式不对称的阳离子 ](+)[BF(4)](-) 只是
• Boev, V. I.; Dombrovskii, A. V., Journal of general chemistry of the USSR, 1987, vol. 57, p. 833 - 837
  作者：Boev, V. I.、Dombrovskii, A. V.

  DOI：——

  日期：——
• ?-Ferrocenylalkylation of the benzotriazole anion
  作者：N. S. Kochetkova、V. I. Boev、L. V. Popova、V. N. Babin

  DOI：10.1007/bf00956100

  日期：1985.6
• Stable and Crystalline Allylium and Allenylium Salts with Ferrocenyl Substituents
  作者：Josef Lukasser、Herbert Angleitner、Herwig Schottenberger、Holger Kopacka、Manuela Schweiger、Benno Bildstein、Karl-Hans Ongania、Klaus Wurst

  DOI：10.1021/om00012a025

  日期：1995.12

  Allylic and allenylic carbenium ions, which have been reported in the literature to be labile or not isolable at all, have no inherent instability. Progressive substitution with ferrocenyl groups affords allylic cations, whose stability toward photochemical decay and nucleophilic collapse increases with increasing number of ferrocenyl substituents, if the allylic moiety is at least 2-fold-substituted with ferrocenes in the 1,3-positions. The unmatched cation-stabilizing capacity of metallocenes is illustrated in cyclopentadienyl( 1,3-diferrocenyl-1-yliumpentalenyl)iron tetrafluoroborate, a compound which survives exposure to sunlight in aqueous solution for days. In addition to full characterization for these allylium salts by the usual analytical and spectroscopic methods, X-ray analysis of cyclopentadienyl(1,3-diferrocenyl- 1-yliumpentalenyl)iron tetrafluoroborate showed (a) deviations of the regular conformation of the ferrocenyl substituents in the 1,3-positions that are similar to those observed in other simple metallocenyl-stabilized carbenium ions, indicative of electronic stabilization by intramolecular charge delocalization, (b) these two ferrocenyl substituents are structurally distorted in an unequal manner and seem to contribute unequally in this charge delocalization, but the observed dissymmetric structure is most likely the result of crystal forces, and (c) the annelated ferrocene of this formal pentalene system is undistorted, ruling out (together with results from solution NMR measurements) any significant conjugation; therefore, this cation should be envisaged as an allylium system and not as an antiaromatic cyclopentadienyl cation. In the case of allenylium <-> propargylium ions, attachment of two ferrocenes results in labile or intermediate propargylium ions, which can be trapped with triethylamine to afford ammonium allenes, formally Lewis base complexed allenylium salts, with an interesting bent allene unit as is evidenced by single-crystal structure analysis. Introduction of a third ferrocene into the allenylium <-> propargylium system affords 1,3,3-triferrocenylallen-1-ylium tetrafluoroborate, the first stable and fully characterized allenylium compound, with only minor resonance contributions from the propargylium structure, proven most clearly by the observation of an extremely intense and acceptor-shifted cumulenic stretching vibration of 2151 cm(-1) in the IR spectrum.