tricarbonyl(1-deuterio-2,4-hexadienol)iron | 172367-69-0

• 英文名称: tricarbonyl(1-deuterio-2,4-hexadienol)iron
• CAS: 172367-69-0；195458-44-7；175273-86-6；195329-35-2；172490-16-3；175273-87-7；175273-85-5
• 化学式: C₉H₁₀FeO₄
• 分子量: 239.015
• InChiKey: JDKUYNABAWHBFY-YHGIMHGJSA-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

• 作为反应物：
  描述：

  hexafluorophosphoric acid 、 tricarbonyl(1-deuterio-2,4-hexadienol)iron 以 溶剂黄146 为溶剂， 以78%的产率得到tricarbonyl(1-exo-deuterio-2,4-hexadienyl)iron hexafluorophosphate
  参考文献：
  名称：

  Reactivity of (Pentadienyl)iron(1+) Cations: Nucleophilic Addition by Phosphines Is Reversible in Certain Cases

  摘要：

  The reaction of (pentadienyl)Fe(CO)(3)(+) cations 1, 5, and 11 with phosphines was examined. At short reaction times, attack of PPh(3) on 1a proceeds at both the unsubstituted and substituted pentadienyl termini to give 2a and 3a, respectively (2:1); however, over a period of ca. 21 h, the minor product 3a isomerizes to the more thermodynamically stable 2a. As the steric bulk of the 1-substituent is increased from methyl to ethyl (1b), kinetic attack by PPh(3) occurs exclusively at the unsubstituted pentadienyl terminus. The complex 2a was characterized crystallographically, and the stereochemistry of PPh(3) attack was established to be opposite to Fe(CO)(3) by use of a stereoselectively labeled cation, d(exo)-1a. The reaction of PPh(3) with 11 initially gives E,Z-12, which isomerizes to E,E-12 over a 22 h period. Reaction with 5 with ((S)-neomenthyl)diphenylphosphine gives two optically active diastereomers, 15a and 15b (3:2 ratio); fractional crystallization gives 15a in greater than 80% mass recovery. In solution, pure 15a isomerizes to a mixture of 15a and 15b (3:2). The interconversions of 3a to 2a, of E,Z-12 to E,E-12, and of 15a and 15b are rationalized by reversible phosphine addition.

  DOI：

  10.1021/om00011a034
• 作为产物：
  描述：

  硼氘化钠 、 tricarbonyl[[2,3,4,5-η]-(2E,4E)-hexa-2,4-dienal]iron 以 四氢呋喃 为溶剂， 以85%的产率得到tricarbonyl(1-deuterio-2,4-hexadienol)iron
  参考文献：
  名称：

  Reactivity of (Pentadienyl)iron(1+) Cations: Nucleophilic Addition by Phosphines Is Reversible in Certain Cases

  摘要：

  The reaction of (pentadienyl)Fe(CO)(3)(+) cations 1, 5, and 11 with phosphines was examined. At short reaction times, attack of PPh(3) on 1a proceeds at both the unsubstituted and substituted pentadienyl termini to give 2a and 3a, respectively (2:1); however, over a period of ca. 21 h, the minor product 3a isomerizes to the more thermodynamically stable 2a. As the steric bulk of the 1-substituent is increased from methyl to ethyl (1b), kinetic attack by PPh(3) occurs exclusively at the unsubstituted pentadienyl terminus. The complex 2a was characterized crystallographically, and the stereochemistry of PPh(3) attack was established to be opposite to Fe(CO)(3) by use of a stereoselectively labeled cation, d(exo)-1a. The reaction of PPh(3) with 11 initially gives E,Z-12, which isomerizes to E,E-12 over a 22 h period. Reaction with 5 with ((S)-neomenthyl)diphenylphosphine gives two optically active diastereomers, 15a and 15b (3:2 ratio); fractional crystallization gives 15a in greater than 80% mass recovery. In solution, pure 15a isomerizes to a mixture of 15a and 15b (3:2). The interconversions of 3a to 2a, of E,Z-12 to E,E-12, and of 15a and 15b are rationalized by reversible phosphine addition.

  DOI：

  10.1021/om00011a034