{1-4-η-5-benzoylcycloheptatriene}iron tricarbonyl | 107493-71-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: {1-4-η-5-benzoylcycloheptatriene}iron tricarbonyl
• 英文别名: carbon monoxide;cyclohepta-1,4,6-trien-1-yl(phenyl)methanone;iron
• CAS: 107493-71-0
• 化学式: C₁₇H₁₂FeO₄
• 分子量: 336.127
• InChiKey: DRVIYIJVXFOEGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  20.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  {1-4-η-5-benzoylcycloheptatriene}iron tricarbonyl 以 甲醇 为溶剂， 以80%的产率得到{1-4-η-6-benzoylcycloheptatriene}iron tricarbonyl
  参考文献：
  名称：

  Isomerization pathways of (acylcycloheptatriene)iron tricarbonyl complexes

  摘要：

  The (7-exo-acylcycloheptatriene)Fe(CO)3 complexes (7-acyl) prepared by acylation of the mild organometallic nucleophile (eta(3)-C7H7)Fe(CO)3- isomerize readily to their 5-acyl and 6-acyl isomers. The 5-acyl isomer can be prepared in high yield by deprotonation of 7-acyl or 6-acyl followed by a proton quench. Refluxing 5- or 7-acyl in methanol gives the 6-acyl isomer. Rate studies have been carried out on the sequential isomerization of 7-acyl to 5-acyl to 6-acyl. Data were obtained by H-1 NMR monitoring in methanol-d4 at 40-degrees-C. The results indicate that both steps of the isomerization involve an intermolecular proton-exchange mechanism. Solvent deprotonation of any of the three acyl isomers gives a common conjugate base that can be reprotonated at three sites. Kinetic protonation gives 5-acyl, and thermodynamic protonation gives 6-acyl. Mass spectral analysis shows small but significant amounts of multiple deuterium incorporation, suggesting that the common anion intermediate can also be protonated at the metal to give a transient iron hydride.

  DOI：

  10.1021/om00037a058
• 作为产物：
  描述：

  {1-4-η-7-exo-benzoylcycloheptatriene}iron tricarbonyl 在 potassium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到{1-4-η-5-benzoylcycloheptatriene}iron tricarbonyl
  参考文献：
  名称：

  Isomerization pathways of (acylcycloheptatriene)iron tricarbonyl complexes

  摘要：

  The (7-exo-acylcycloheptatriene)Fe(CO)3 complexes (7-acyl) prepared by acylation of the mild organometallic nucleophile (eta(3)-C7H7)Fe(CO)3- isomerize readily to their 5-acyl and 6-acyl isomers. The 5-acyl isomer can be prepared in high yield by deprotonation of 7-acyl or 6-acyl followed by a proton quench. Refluxing 5- or 7-acyl in methanol gives the 6-acyl isomer. Rate studies have been carried out on the sequential isomerization of 7-acyl to 5-acyl to 6-acyl. Data were obtained by H-1 NMR monitoring in methanol-d4 at 40-degrees-C. The results indicate that both steps of the isomerization involve an intermolecular proton-exchange mechanism. Solvent deprotonation of any of the three acyl isomers gives a common conjugate base that can be reprotonated at three sites. Kinetic protonation gives 5-acyl, and thermodynamic protonation gives 6-acyl. Mass spectral analysis shows small but significant amounts of multiple deuterium incorporation, suggesting that the common anion intermediate can also be protonated at the metal to give a transient iron hydride.

  DOI：

  10.1021/om00037a058

文献信息

• Regio- and stereocontrolled functionalization of a seven-membered ring via (cycloheptatriene)iron tricarbonyl
  作者：Gregory M. Williams、Duane E. Rudisill、Beverly A. Barnum、Kenneth Hardcastle、Richard H. Heyn、Christopher J. Kozak、Jeffrey W. McMillan

  DOI：10.1021/ja00157a033

  日期：1990.1

  Deprotonation of (cycloheptatriene) Fe(CO) 3 gives a deep red nucleophilic anion (C 7 H 7 )Fe(CO) 3 (K + ), Anion reacts with acid chlorides to give (7-exo-acyl-C 7 H 7 ) Fe(CO) 3 complexes, in high yield. The products were characterized by spectroscopic techniques and by a single-crystal X-ray diffraction study on the benzoyl derivative: crystallizes in the monoclinic space group P2 1 /c

  (环庚三烯) Fe(CO) 3 的去质子化得到深红色的亲核阴离子 (C 7 H 7 )Fe(CO) 3 (K + )，阴离子与酰氯反应得到 (7-exo-acyl-C 7 H 7 ) Fe(CO) 3 配合物，收率高。通过光谱技术和对苯甲酰衍生物的单晶 X 射线衍射研究对产物进行表征：在单斜晶系 P2 1 /c 空间群中结晶
• WILLIAMS G. M.; RUDISILL D. E., TETRAHEDRON LETT., 27,(1986) N 30, 3465-3468
  作者：WILLIAMS G. M.、 RUDISILL D. E.

  DOI：——

  日期：——