1-(4-{2-[2-(4-Propynoyl-benzyloxy)-ethoxy]-ethoxymethyl}-phenyl)-propynone | 441799-32-2

• 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: 1-(4-{2-[2-(4-Propynoyl-benzyloxy)-ethoxy]-ethoxymethyl}-phenyl)-propynone
• 英文别名: 1-[4-[2-[2-[(4-Prop-2-ynoylphenyl)methoxy]ethoxy]ethoxymethyl]phenyl]prop-2-yn-1-one
• CAS: 441799-32-2
• 化学式: C₂₄H₂₂O₅
• 分子量: 390.436
• InChiKey: HOIPFAKZPCQCEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-dimethylamino-1-(3-methoxyphenyl)-prop-2-en-1-one 、 1-(4-{2-[2-(4-Propynoyl-benzyloxy)-ethoxy]-ethoxymethyl}-phenyl)-propynone 以 二氯甲烷 、 甲苯 为溶剂， 以39%的产率得到5-(3-Methoxybenzoyl)-14,17,20-trioxatetracyclo[20.2.2.29,12.13,7]nonacosa-1(24),3(29),4,6,9(28),10,12(27),22,25-nonaene-2,8-dione
  参考文献：
  名称：

  An Enaminone-Directed Benzannulation/Macrocyclization Approach to Cyclophane Ring Systems

  摘要：

  A straightforward and modular preparative approach to 1,3,5-triaroylbenzene-based functionalized cyclophane ring systems has been developed. The key cyclophane-forming macrocyclization reaction was accomplished during the course of a regioselective cross-benzannulation between bis(aryl ethynyl) ketone and enaminone reactants. Macrocyclic products with ring sizes ranging from 18-to 22-membered were successfully constructed. The composition of the tether connecting the two aryl ethynyl ketone fragments can be easily varied; consequently, this method is suitable for construction of a diverse range of structurally distinct cyclophane products. To illustrate this feature, cyclophanes possessing xylyl, alkyl, di(ethylene triamine), and di(ethylene oxy) bridging units were synthesized in isolated yields of 11-46%. Three new cyclophanes (calixarene-like macrocyles 8 and 9, as well as crownophane 18) were structurally characterized by X-ray diffractometry.

  DOI：

  10.1021/jo0256181
• 作为产物：
  描述：

  4,4'-(2,2'-oxybis(ethane-2,1-diyl)bis(oxy))bis(methylene)bis(bromobenzene) 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 1-(4-{2-[2-(4-Propynoyl-benzyloxy)-ethoxy]-ethoxymethyl}-phenyl)-propynone
  参考文献：
  名称：

  An Enaminone-Directed Benzannulation/Macrocyclization Approach to Cyclophane Ring Systems

  摘要：

  A straightforward and modular preparative approach to 1,3,5-triaroylbenzene-based functionalized cyclophane ring systems has been developed. The key cyclophane-forming macrocyclization reaction was accomplished during the course of a regioselective cross-benzannulation between bis(aryl ethynyl) ketone and enaminone reactants. Macrocyclic products with ring sizes ranging from 18-to 22-membered were successfully constructed. The composition of the tether connecting the two aryl ethynyl ketone fragments can be easily varied; consequently, this method is suitable for construction of a diverse range of structurally distinct cyclophane products. To illustrate this feature, cyclophanes possessing xylyl, alkyl, di(ethylene triamine), and di(ethylene oxy) bridging units were synthesized in isolated yields of 11-46%. Three new cyclophanes (calixarene-like macrocyles 8 and 9, as well as crownophane 18) were structurally characterized by X-ray diffractometry.

  DOI：

  10.1021/jo0256181

文献信息

• An Enaminone-Directed Benzannulation/Macrocyclization Approach to Cyclophane Ring Systems
  作者：F. Christopher Pigge、Fatemeh Ghasedi、Nigam P. Rath

  DOI：10.1021/jo0256181

  日期：2002.6.1

  A straightforward and modular preparative approach to 1,3,5-triaroylbenzene-based functionalized cyclophane ring systems has been developed. The key cyclophane-forming macrocyclization reaction was accomplished during the course of a regioselective cross-benzannulation between bis(aryl ethynyl) ketone and enaminone reactants. Macrocyclic products with ring sizes ranging from 18-to 22-membered were successfully constructed. The composition of the tether connecting the two aryl ethynyl ketone fragments can be easily varied; consequently, this method is suitable for construction of a diverse range of structurally distinct cyclophane products. To illustrate this feature, cyclophanes possessing xylyl, alkyl, di(ethylene triamine), and di(ethylene oxy) bridging units were synthesized in isolated yields of 11-46%. Three new cyclophanes (calixarene-like macrocyles 8 and 9, as well as crownophane 18) were structurally characterized by X-ray diffractometry.