1-(2-ethynyl-3,4,5-trimethoxyphenyl)ethan-1-ol | 1101084-03-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(2-ethynyl-3,4,5-trimethoxyphenyl)ethan-1-ol
• CAS: 1101084-03-0
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: DEKHPJULTIYLNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.75
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-(2-ethynyl-3,4,5-trimethoxyphenyl)ethan-1-ol 、 1-bromo-5-oxaocta-2,7-diyne 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 0.17h， 以80%的产率得到4-Ethynyl-1,2,3-trimethoxy-5-[1-(4-prop-2-ynoxybut-2-ynoxy)ethyl]benzene
  参考文献：
  名称：

  A [2 + 2 + 2]-Cycloaddition Approach toward 6-Oxa-allocolchicinoids with Apoptosis-Inducing Activity

  摘要：

  Following an A -> ABC strategy, a new synthesis of 6-oxa-allocolchicinoids was developed exploiting a microwave-promoted Co- or Rh-catalyzed intramolecular [2 + 2 + 2]-cycloaddition (alkyne cyclotrimerization) as a key step. The approach opens a short and efficient access to a variety of novel compounds, some of which were found to exhibit significant and selective apoptosis-inclucing activities against BJAB tumor cells.

  DOI：

  10.1021/ol802542c
• 作为产物：
  描述：

  在 sodium tetrahydroborate 、 potassium fluoride 、 氯化铵 作用下， 以 甲醇 为溶剂， 以79%的产率得到1-(2-ethynyl-3,4,5-trimethoxyphenyl)ethan-1-ol
  参考文献：
  名称：

  A [2 + 2 + 2]-Cycloaddition Approach toward 6-Oxa-allocolchicinoids with Apoptosis-Inducing Activity

  摘要：

  Following an A -> ABC strategy, a new synthesis of 6-oxa-allocolchicinoids was developed exploiting a microwave-promoted Co- or Rh-catalyzed intramolecular [2 + 2 + 2]-cycloaddition (alkyne cyclotrimerization) as a key step. The approach opens a short and efficient access to a variety of novel compounds, some of which were found to exhibit significant and selective apoptosis-inclucing activities against BJAB tumor cells.

  DOI：

  10.1021/ol802542c

文献信息

• Synthesis of Novel Allocolchicine Analogues with a Pyridine C-Ring through Intermolecular Vollhardt Diyne-Nitrile Cyclotrimerization
  作者：Hans-Günther Schmalz、Norman Nicolaus

  DOI：10.1055/s-0030-1258512

  日期：2010.9

  A short synthesis of new allocolchicinoids with a pyridine C-ring and an oxa-B-ring was developed exploiting a cobalt-catalyzed intermolecular [2+2+2] cycloaddition (diyne-nitrile cyclotrimerization). Starting from readily accessible 3,4,5-trimethoxybenzaldehyde or 3,4,5-trimethoxyacetophenone, the (racemic) target compounds were regioselectively obtained in 15-20% overall yield (five steps).

  利用钴催化的分子间 [2+2+2] 环加成（二炔-腈环三聚），开发了具有吡啶 C 环和氧杂 B 环的新型别秋水仙素的短合成。从容易获得的 3,4,5-三甲氧基苯甲醛或 3,4,5-三甲氧基苯乙酮开始，以 15-20% 的总产率（五个步骤）区域选择性地获得（外消旋）目标化合物。