2-[4-[(2-Ethynyl-3,4,5-trimethoxyphenyl)methoxy]but-2-ynoxy]acetonitrile | 1101083-79-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[4-[(2-Ethynyl-3,4,5-trimethoxyphenyl)methoxy]but-2-ynoxy]acetonitrile
• 英文别名: 2-[4-[(2-ethynyl-3,4,5-trimethoxyphenyl)methoxy]but-2-ynoxy]acetonitrile
• CAS: 1101083-79-7
• 化学式: C₁₈H₁₉NO₅
• 分子量: 329.353
• InChiKey: PERADJVYIAKLNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  69.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[4-[(2-Ethynyl-3,4,5-trimethoxyphenyl)methoxy]but-2-ynoxy]acetonitrile 在 carbon monoxide,cobalt,cyclopenta-1,3-diene 、 三苯基膦 作用下， 以 氯苯 为溶剂， 反应 0.5h， 以71%的产率得到3,4,5-Trimethoxy-9,14-dioxa-17-azatetracyclo[9.7.0.02,7.012,16]octadeca-1(18),2,4,6,11,16-hexaene
  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：

  6-cyano-5-oxahexa-2-yne-1-ol 、 2-Ethynyl-1-(iodomethyl)-3,4,5-trimethoxybenzene 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 以88%的产率得到2-[4-[(2-Ethynyl-3,4,5-trimethoxyphenyl)methoxy]but-2-ynoxy]acetonitrile
  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

• A [2 + 2 + 2]-Cycloaddition Approach toward 6-Oxa-allocolchicinoids with Apoptosis-Inducing Activity
  作者：Norman Nicolaus、Susanne Strauss、Jörg-Martin Neudörfl、Aram Prokop、Hans-Günther Schmalz

  DOI：10.1021/ol802542c

  日期：2009.1.15

  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.