tricarbonyl[(1-4-η)-2-methoxy-5-methylenecyclohexa-1,3-diene]iron | 86664-11-1

• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 英文名称: tricarbonyl[(1-4-η)-2-methoxy-5-methylenecyclohexa-1,3-diene]iron
• 英文别名: carbon monoxide;iron;2-methoxy-5-methylidenecyclohexa-1,3-diene
• CAS: 86664-11-1
• 化学式: C₁₁H₁₀FeO₄
• 分子量: 262.045
• InChiKey: DHLDBNOTGRTVRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.92
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  12.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tricarbonyl[(1-4-η)-2-methoxy-5-methylenecyclohexa-1,3-diene]iron 、 硝基丙烷 在 苯甲腈 N-氧化物 、 三乙胺 作用下， 以 苯 为溶剂， 以70%的产率得到tricarbonyl((6-9-η)-3-ethyl-8-methoxy-1,2-oxaazaspiro[4.5]deca-2,6,8-triene)iron
  参考文献：
  名称：

  1,3-Dipolar Cycloaddition to Tricarbonyl[(1−4-η)-2- methoxy-5-methylenecyclohexa-1,3-diene]iron:  Rapid Construction of a Spiro[4.5]decane System

  摘要：

  Tricarbonyl[(1-4-eta)-2-methoxy-5-methyl-enecyclohexa-1,3-diene]iron (1) undergoes 1,3-dipolar cycloaddition reaction regio-, stereo-, and chemoselectively at its exocyclic double bond, yielding a spiro[4.5]-decane system. Reactive 1,3-dipoles with low-lying LUMO's such as nitrile oxides, ozone, diazoacetate, and oxoallyl cation participate well in cycloaddition to give isoxazole, ketone, pyrazoline, and cyclopentanone adducts, respectively. The complex 1 can be viewed as the synthetic equivalent of synthon 2 and has been illustrated for the first time as a versatile synthetic intermediate.

  DOI：

  10.1021/om950770x
• 作为产物：
  描述：

  tricarbonyl[(1-5-η)-4-methoxy-1-methylcyclohexa-2,4-dienyl]iron hexafluorophosphate 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以98%的产率得到tricarbonyl[(1-4-η)-2-methoxy-5-methylenecyclohexa-1,3-diene]iron
  参考文献：
  名称：

  1,3-Dipolar Cycloaddition to Tricarbonyl[(1−4-η)-2- methoxy-5-methylenecyclohexa-1,3-diene]iron:  Rapid Construction of a Spiro[4.5]decane System

  摘要：

  Tricarbonyl[(1-4-eta)-2-methoxy-5-methyl-enecyclohexa-1,3-diene]iron (1) undergoes 1,3-dipolar cycloaddition reaction regio-, stereo-, and chemoselectively at its exocyclic double bond, yielding a spiro[4.5]-decane system. Reactive 1,3-dipoles with low-lying LUMO's such as nitrile oxides, ozone, diazoacetate, and oxoallyl cation participate well in cycloaddition to give isoxazole, ketone, pyrazoline, and cyclopentanone adducts, respectively. The complex 1 can be viewed as the synthetic equivalent of synthon 2 and has been illustrated for the first time as a versatile synthetic intermediate.

  DOI：

  10.1021/om950770x

文献信息

• Tricarbonyl[(1−4-η)-2-Methoxy-5-methylenecyclohexa- 1,3-diene]iron as a Synthetic Intermediate:  Sequential Electrophilic and Nucleophilic Additions
  作者：Chi Wi Ong、Junn Nan Wang、Ting Ling Chien

  DOI：10.1021/om970684s

  日期：1998.3.1

  Tricarbonyl[(1−4-η)-2-methoxy-5-methylenecyclohexa-1,3-diene]iron reacts with electrophiles to give the cyclohexadienylium−Fe(CO)3 cation, which either reacts with nucleophiles to form a new quaternary center or undergoes competitive loss of an acidic α-proton to give a new triene complex. This constitutes a new reaction sequence for the synthesis of 4,4-disubstituted cyclohexen-2-ones with the simultaneous

  三羰基[（1-4-η）-2-甲氧基-5-亚甲基环己-1,3-二烯]铁与亲电试剂反应生成环己二烯基-Fe（CO）3阳离子，后者与亲核试剂反应形成新的季铵盐使酸性α-质子居中或经历竞争性损失而生成新的三烯络合物。这构成了合成4,4-二取代的环己烯-2-酮并同时引入两个官能团的新反应序列。
• Howell, James A. S.; Thomas, Marian J., Organometallics, 1985, vol. 4, # 6, p. 1054 - 1059
  作者：Howell, James A. S.、Thomas, Marian J.

  DOI：——

  日期：——
• HOWELL, J. A. S.;THOMAS, M. J., J. ORGANOMET. CHEM., 1983, 247, N 2, C21-C23
  作者：HOWELL, J. A. S.、THOMAS, M. J.

  DOI：——

  日期：——
• HOWELL, J. A. S.;THOMAS, M. J., ORGANOMETALLICS, 1985, 4, N 6, 1054-1059
  作者：HOWELL, J. A. S.、THOMAS, M. J.

  DOI：——

  日期：——
• PEARSON, ANTHONY J.;OBRIEN, MICHAEL K., J. CHEM. SOC. CHEM. COMMUN.,(1987) N 19, 1445-1447
  作者：PEARSON, ANTHONY J.、OBRIEN, MICHAEL K.

  DOI：——

  日期：——