(Z,Z)-[4.4](2,8)dibenzothiophenophane-2,15-diene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: (Z,Z)-[4.4](2,8)dibenzothiophenophane-2,15-diene
• 英文别名: (8Z,22Z)-30,32-dithiaheptacyclo[23.3.1.12,6.13,28.111,15.114,17.116,20]tetratriaconta-1(28),2,4,6(34),8,11(33),12,14,16,18,20(31),22,25(29),26-tetradecaene
• 化学式: C₃₂H₂₄S₂
• 分子量: 472.675
• InChiKey: YOSKYBSAJKXRDN-LOKDLIDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.7
• 重原子数：
  34
• 可旋转键数：
  0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  二苯并噻吩 在 Grubbs catalyst first generation 溴 、 三苯基膦 、 palladium dichloride 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 39.0h， 生成 (Z,Z)-[4.4](2,8)dibenzothiophenophane-2,15-diene
  参考文献：
  名称：

  摘要：

  Some novel dibenzothiophen amino acid and cyclophane derivatives have been produced as a result of synthetic studies on the development of dibenzothiophen-based antibacterial compounds. Allylation through a Stille reaction has produced 2-allyl-8-bromodibenzothiophen (3a) and 2,8-diallyldibenzothiophen (3b). Under different conditions, the Stille reaction also produced 2-bromo-8-(prop-1-enyl)dibenzothiophen (4a) and 2,8-di(prop-1-enyl)dibenzothiophen (4b) via double bond isomerization. Olefin metathesis with (3b) and methyl N-acetylallylglycinate (5) produced two homodimers, the novel [4](5,11)[4](18,24)dibenzothiophenophane-2,15-diene (6), as a mixture of geometrical isomers, and dimethyl (E)- and (Z)-(R,S)-2,7-diacetamidooct-4-enedioate (8), and the two cross-metathesis products methyl (E)- and (Z)-( R, S)-2-acetamido-6-(8-allyldibenzothien-2-yl)hex-4-enoate (7a) and dimethyl (E)- and (Z)-(R,S)- 6,6'-(dibenzothiophen-2,8-diyl)bis(2-acetamidohex-4-enoate) (7b). Palladium-catalysed hydrogenation of the homodimer (6) and the cross-metathesis products (7a,b) yielded the corresponding reduced compounds (9) and (10a,b), respectively.

  DOI：

  10.1071/ch00029