(+/-)-2-(2-(4-methoxyphenyl)-1,3-dioxan-4-yl)ethanol | 302783-35-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (+/-)-2-(2-(4-methoxyphenyl)-1,3-dioxan-4-yl)ethanol
• 英文别名: 2-[2-(4-Methoxyphenyl)-1,3-dioxan-4-yl]ethanol
• CAS: 302783-35-3
• 化学式: C₁₃H₁₈O₄
• 分子量: 238.284
• InChiKey: FRLIXFZIJWKKEY-UHFFFAOYSA-N

物化性质

• 沸点：
  381.9±37.0 °C(Predicted)
• 密度：
  1.124±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-2-(2-(4-methoxyphenyl)-1,3-dioxan-4-yl)ethanol 在 三正丁基氢锡 、 magnesium bromide 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以96%的产率得到5-(4-Methoxy-benzyloxy)-pentane-1,3-diol
  参考文献：
  名称：

  Facile chelation-controlled reductive opening of methoxybenzylidene acetals with Bu3SnH and MgBr2. Regioselective protection strategy as MPM ethers

  摘要：

  A mild and efficient regioselective reductive opening of methoxybenzylidene acetals using a combination of Bu3SnH and MgBr2. OEt2, mainly via five-membered chelation intermediates is described. This reaction was applied to synthetic intermediates of myriaporon and tedanolide. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01017-0
• 作为产物：
  描述：

  1,3,5-戊三醇 、 4-甲氧基苯甲醛二甲缩醛 在 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以6.95 g的产率得到(+/-)-2-(2-(4-methoxyphenyl)-1,3-dioxan-4-yl)ethanol
  参考文献：
  名称：

  通过酰基乙烯酮的双大内酯化/吡喃-半缩酮形成：在合成（-）-callipeltoside A和lyngbyaloside B模型系统中的应用。

  摘要：

  Thermal generation of acylketenes in diol-containing substrates results in dual macrocyclization/pyran-hemiketal formation. This transformation expands the scope of acylketene macrolactonizations and their application to the synthesis of complex macrolides. Triol and even tetrol substrates also have been closed in highly regioselective fashion. Additionally, the challenging macrolactonization of a tertiary alcohol was achieved.

  DOI：

  10.1002/anie.200804049

文献信息

• Facile chelation-controlled reductive opening of methoxybenzylidene acetals with Bu3SnH and MgBr2. Regioselective protection strategy as MPM ethers
  作者：Bao-Zhong Zheng、Megumi Yamauchi、Hiroo Dei、Shin-ichi Kusaka、Katsuya Matsui、Osamu Yonemitsu

  DOI：10.1016/s0040-4039(00)01017-0

  日期：2000.8

  A mild and efficient regioselective reductive opening of methoxybenzylidene acetals using a combination of Bu3SnH and MgBr2. OEt2, mainly via five-membered chelation intermediates is described. This reaction was applied to synthetic intermediates of myriaporon and tedanolide. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Dual Macrolactonization/Pyran-Hemiketal Formation via Acylketenes: Applications to the Synthesis of (−)-Callipeltoside A and a Lyngbyaloside B Model System
  作者：Thomas R. Hoye、Michael E. Danielson、Aaron E. May、Hongyu Zhao

  DOI：10.1002/anie.200804049

  日期：2008.12.1

  Thermal generation of acylketenes in diol-containing substrates results in dual macrocyclization/pyran-hemiketal formation. This transformation expands the scope of acylketene macrolactonizations and their application to the synthesis of complex macrolides. Triol and even tetrol substrates also have been closed in highly regioselective fashion. Additionally, the challenging macrolactonization of a tertiary alcohol was achieved.