3,5-Bis-(2-{4-[2-(3-ethynyl-5-methylphenyl)ethynyl]-2-propyloxy-5-(tetrahydro-2H-pyran-2-yloxy)phenyl}ethynyl)toluene | 174536-26-6

• 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: 3,5-Bis-(2-{4-[2-(3-ethynyl-5-methylphenyl)ethynyl]-2-propyloxy-5-(tetrahydro-2H-pyran-2-yloxy)phenyl}ethynyl)toluene
• 英文别名: 2-[2-[2-(3-Ethynyl-5-methylphenyl)ethynyl]-5-[2-[3-[2-[4-[2-(3-ethynyl-5-methylphenyl)ethynyl]-5-(oxan-2-yloxy)-2-propoxyphenyl]ethynyl]-5-methylphenyl]ethynyl]-4-propoxyphenoxy]oxane
• CAS: 174536-26-6
• 化学式: C₆₁H₅₆O₆
• 分子量: 885.112
• InChiKey: KELLBRADMGZJMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15
• 重原子数：
  67
• 可旋转键数：
  20
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,5-Bis-(2-{4-[2-(3-ethynyl-5-methylphenyl)ethynyl]-2-propyloxy-5-(tetrahydro-2H-pyran-2-yloxy)phenyl}ethynyl)toluene 在 吡啶 、 copper(l) chloride 、 copper dichloride 作用下， 反应 96.0h， 以45%的产率得到2-[[6,19,28,41,54,63-Hexamethyl-34,69,75-tris(oxan-2-yloxy)-47,71,78,83-tetrapropoxy-13-undecacyclo[66.2.2.211,14.233,36.246,49.14,8.117,21.126,30.139,43.152,56.161,65]tetraoctaconta-1(71),4,6,8(84),11(83),12,14(82),17,19,21(81),26(80),27,29,33(79),34,36(78),39(77),40,42,46,48,52,54,56(74),61(73),62,64,68(72),69,75-triacontaen-2,9,15,22,24,31,37,44,50,57,59,66-dodecaynyl]oxy]oxane
  参考文献：
  名称：

  Synthesis and Properties of Shape-Persistent Macrocyclic Amphiphiles with Switchable Amphiphilic Portions

  摘要：

  The bidirectional- and convergent-type syntheses of functionalized kinked phenyl-ethynyl oligomers containing ethynyl end groups are described. Key steps in both approaches are the bromo-iodo selectivity of the Hagihara coupling and the possibility to deprotect acetylenes containing different silyl protective groups stepwise. Glaser coupling of the oligomeric bisacetylenes results in the corresponding macrocycles that contain polar and nonpolar side groups in a switchable arrangement.

  DOI：

  10.1002/(sici)1521-3765(19981204)4:12<2423::aid-chem2423>3.0.co;2-8
• 作为产物：
  描述：

  3,5-Bis-{2-[2-propyloxy-5-(tetrahydro-2H-pyran-2-yloxy)-4-(2-triisopropylsilylethynyl)phenyl]ethynyl}toluene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 哌啶 、 sodium hydroxide 、 四丁基氟化铵 、 水 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.0h， 生成 3,5-Bis-(2-{4-[2-(3-ethynyl-5-methylphenyl)ethynyl]-2-propyloxy-5-(tetrahydro-2H-pyran-2-yloxy)phenyl}ethynyl)toluene
  参考文献：
  名称：

  Synthesis and Properties of Shape-Persistent Macrocyclic Amphiphiles with Switchable Amphiphilic Portions

  摘要：

  The bidirectional- and convergent-type syntheses of functionalized kinked phenyl-ethynyl oligomers containing ethynyl end groups are described. Key steps in both approaches are the bromo-iodo selectivity of the Hagihara coupling and the possibility to deprotect acetylenes containing different silyl protective groups stepwise. Glaser coupling of the oligomeric bisacetylenes results in the corresponding macrocycles that contain polar and nonpolar side groups in a switchable arrangement.

  DOI：

  10.1002/(sici)1521-3765(19981204)4:12<2423::aid-chem2423>3.0.co;2-8

文献信息

• Structure and Temperature Effects on the Cyclization of Rigid Bisacetylenes
  作者：Sigurd Höger、Klaus Bonrad、Lars Karcher、Anne-Désirée Meckenstock

  DOI：10.1021/jo991644w

  日期：2000.3.1
• Hoeger, Sigurd; Enkelmann, Volker, Angewandte Chemie, 1995, vol. 107, # 23/24, p. 2917 - 2919
  作者：Hoeger, Sigurd、Enkelmann, Volker

  DOI：——

  日期：——