carbon monoxide;iron;methyl (2E,4E)-6,6-dimethoxyhexa-2,4-dienoate | 143395-21-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: carbon monoxide;iron;methyl (2E,4E)-6,6-dimethoxyhexa-2,4-dienoate
• CAS: 143395-21-5；126213-74-9
• 化学式: C₁₂H₁₄FeO₇
• 分子量: 326.086
• InChiKey: IDIXFIBOICNSAM-LTKQDOIVSA-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：

  carbon monoxide;iron;methyl (2E,4E)-6,6-dimethoxyhexa-2,4-dienoate 、 重氧水 在 硫酸 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Acid-catalyzed cyclization of 1,4-diols tethered to (butadiene)iron tricarbonyl segments. Isotopic labeling as a mechanistic probe of stereochemical retention during tetrahydrofuran formation

  摘要：

  1,4-Butanediols can undergo acid-catalyzed dehydrative cyclization by either of two pathways. Selected 1-(3-hydroxypropyl) cyclohexanols have previously been shown to prefer the intramolecular S(N)2 option where displacement of water by the more highly substituted carbinol oxygen atom operates. All four O-18-labeled 1,4-diols prepared in this study, constructed so as to carry the secondary hydroxyl immediately adjacent to a tricarbonyliron-complexed diene, choose the alternative S(N)1 option. As a consequence, all of the isotopic content is absent in the tetrahydrofuran products, and stereochemical integrity is not preserved. Control experiments performed under the same mild conditions reveal product equilibration to be facile. Consequently, the opposite mechanistic extreme is followed by these systems. Other ground-state and transition-state considerations are discussed.

  DOI：

  10.1021/ja00049a015
• 作为产物：
  描述：

  tricarbonyl(methyl 6-oxo-2,4-hexadienoate)iron 在 对甲苯磺酸 、 三乙胺 、 原甲酸三甲酯 作用下， 以 乙醇 为溶剂， 以96%的产率得到carbon monoxide;iron;methyl (2E,4E)-6,6-dimethoxyhexa-2,4-dienoate
  参考文献：
  名称：

  Acid-catalyzed cyclization of 1,4-diols tethered to (butadiene)iron tricarbonyl segments. Isotopic labeling as a mechanistic probe of stereochemical retention during tetrahydrofuran formation

  摘要：

  1,4-Butanediols can undergo acid-catalyzed dehydrative cyclization by either of two pathways. Selected 1-(3-hydroxypropyl) cyclohexanols have previously been shown to prefer the intramolecular S(N)2 option where displacement of water by the more highly substituted carbinol oxygen atom operates. All four O-18-labeled 1,4-diols prepared in this study, constructed so as to carry the secondary hydroxyl immediately adjacent to a tricarbonyliron-complexed diene, choose the alternative S(N)1 option. As a consequence, all of the isotopic content is absent in the tetrahydrofuran products, and stereochemical integrity is not preserved. Control experiments performed under the same mild conditions reveal product equilibration to be facile. Consequently, the opposite mechanistic extreme is followed by these systems. Other ground-state and transition-state considerations are discussed.

  DOI：

  10.1021/ja00049a015

文献信息

• GALL, THIERRY LE;LELLOUCHE, JEAN-PAUL;TOUPET, LOIC;BEAUCOURT, JEAN-PIERRE, TETRAHEDRON. LETT., 30,(1989) N7, C. 6517-6520
  作者：GALL, THIERRY LE、LELLOUCHE, JEAN-PAUL、TOUPET, LOIC、BEAUCOURT, JEAN-PIERRE

  DOI：——

  日期：——