[4-[7-[4-(Hydroxymethyl)phenyl]-4,4-bis(methoxymethyl)hepta-1,6-diynyl]phenyl]methanol | 1605284-08-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: [4-[7-[4-(Hydroxymethyl)phenyl]-4,4-bis(methoxymethyl)hepta-1,6-diynyl]phenyl]methanol
• 英文别名: [4-[7-[4-(hydroxymethyl)phenyl]-4,4-bis(methoxymethyl)hepta-1,6-diynyl]phenyl]methanol
• CAS: 1605284-08-9
• 化学式: C₂₅H₂₈O₄
• 分子量: 392.495
• InChiKey: MKZZSNRRHUSCJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [4-[7-[4-(Hydroxymethyl)phenyl]-4,4-bis(methoxymethyl)hepta-1,6-diynyl]phenyl]methanol 、 三乙二醇二(对甲苯磺酸酯) 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 3.0h， 以33%的产率得到5,5-Bis(methoxymethyl)-14,17,20,23-tetraoxatricyclo[23.2.2.29,12]hentriaconta-1(28),9,11,25(29),26,30-hexaen-2,7-diyne
  参考文献：
  名称：

  A Strain Induced Change of Mechanism from a [2 + 2 + 2] to a [2 + 1 + 2 + 1] Cycloaddition Reaction

  摘要：

  While investigating the [2 + 2 + 2] cycloaddition as a tool to build up strained oligophenyl systems with a diyne-ethylene glycol macrocyle, a surprising change of mechanism was observed. Instead of the expected [2 + 2 + 2] para-terphenyl, the ortho-terphenyl product explained by a formal [2 + 1 + 2 + 1] cycloaddition was formed. An eta(4)-coordinated metal-cyclobutadiene is proposed as the key structure in the catalytic cycle, which is formed to release the induced strain. The optical properties of the ortho-terphenyl products have been measured as well as the coordination ability of Na+ and K+.

  DOI：

  10.1021/ol5007604
• 作为产物：
  描述：

  4-碘苯甲酸 在 copper(l) iodide 、 四(三苯基膦)钯 、 dimethyl sulfide borane 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 生成 [4-[7-[4-(Hydroxymethyl)phenyl]-4,4-bis(methoxymethyl)hepta-1,6-diynyl]phenyl]methanol
  参考文献：
  名称：

  A Strain Induced Change of Mechanism from a [2 + 2 + 2] to a [2 + 1 + 2 + 1] Cycloaddition Reaction

  摘要：

  While investigating the [2 + 2 + 2] cycloaddition as a tool to build up strained oligophenyl systems with a diyne-ethylene glycol macrocyle, a surprising change of mechanism was observed. Instead of the expected [2 + 2 + 2] para-terphenyl, the ortho-terphenyl product explained by a formal [2 + 1 + 2 + 1] cycloaddition was formed. An eta(4)-coordinated metal-cyclobutadiene is proposed as the key structure in the catalytic cycle, which is formed to release the induced strain. The optical properties of the ortho-terphenyl products have been measured as well as the coordination ability of Na+ and K+.

  DOI：

  10.1021/ol5007604

文献信息

• A Strain Induced Change of Mechanism from a [2 + 2 + 2] to a [2 + 1 + 2 + 1] Cycloaddition Reaction
  作者：Anne-Florence Tran-Van、Silas Götz、Markus Neuburger、Hermann A. Wegner

  DOI：10.1021/ol5007604

  日期：2014.5.2

  While investigating the [2 + 2 + 2] cycloaddition as a tool to build up strained oligophenyl systems with a diyne-ethylene glycol macrocyle, a surprising change of mechanism was observed. Instead of the expected [2 + 2 + 2] para-terphenyl, the ortho-terphenyl product explained by a formal [2 + 1 + 2 + 1] cycloaddition was formed. An eta(4)-coordinated metal-cyclobutadiene is proposed as the key structure in the catalytic cycle, which is formed to release the induced strain. The optical properties of the ortho-terphenyl products have been measured as well as the coordination ability of Na+ and K+.