trans-1,4-bis(trimethylsilylethynyl)cyclohexa-2,5-diene-1,4-diol | 544706-65-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans-1,4-bis(trimethylsilylethynyl)cyclohexa-2,5-diene-1,4-diol
• 英文别名: trans-1,4-bis(trimethylsilylethynyl)cyclohexa-2,5-dien-1,4-diol
• CAS: 544706-65-2
• 化学式: C₁₆H₂₄O₂Si₂
• 分子量: 304.536
• InChiKey: SSFUVNKTJYUYQD-WKILWMFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  20.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  trans-1,4-bis(trimethylsilylethynyl)cyclohexa-2,5-diene-1,4-diol 在 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 4.0h， 生成 2,5-diethynyloxepin
  参考文献：
  名称：

  Synthesis of 2,5-diethynyl substituted oxepins from trans-1,4-diethynylcyclohexa-2,5-diene-1,4-diols

  摘要：

  Reaction of trans-1,4-bis(trimethylsilylethynyl)cyclohexa-2,5-diene-1,4-diol with n-BuLi followed by methanesulfonyl chloride resulted in the formation of a dark red solid, which was identified as 2,5-bis(trimethylsilylethynyl)oxepin. Deprotection of the silyl groups resulted in the formation of 2,5-diethynyloxepin, a red, shock sensitive solid. Reaction of a differentially substituted cyclohexa-2,5-diene-1,4-diol gave a mixture of 2,5-diethynyl substituted oxepins. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.044
• 作为产物：
  描述：

  lithium trimethylsilylacetylenide 、 对苯醌 生成 trans-1,4-bis(trimethylsilylethynyl)cyclohexa-2,5-diene-1,4-diol 、 cis-1,4-bis(trimethylsilylethynyl)cyclohexa-2,5-dien-1,4-diol
  参考文献：
  名称：

  Synthesis of Strained Pyridine-Containing Cyclyne via Reductive Aromatization

  摘要：

  The Sonogashira-Hagihara coupling reactions of 2,6-diiodopyridine and cis-3,6-diethynyl-3,6-dimethoxycy-clohexa-1,4-diene or cis-9,10-diethynyl-9,10-dimethoxy-9, 10-dihydroanthracene gave macrocyclic compounds having alternating 2,6-diethynylpyridine and 3,6-dimethoxycyclohexa-1,4-diene segments. Transformation of the C(3)-symmetric 2,6-diethynylpyridine-based cyclo-trimer was efficiently achieved using tin-mediated reductive aromatization under mild conditions.

  DOI：

  10.1021/jo1006202

文献信息

• Synthesis of Buta-1,3-diyne-Bridged Macrocycles with (Z)-1,4-Diethynyl1,4-dimethoxycyclohexa-2,5-diene as the Building Block
  作者：Manivannan Srinivasan、Sethuraman Sankararaman、Henning Hopf、Babu Varghese

  DOI：10.1002/ejoc.200390106

  日期：2003.2

  (Z)-1,4-Diethynyl-1,4-dimethoxycyclohexa-2,5-diene has been used as a building block for the synthesis of two novel macrocycles containing buta-1,3-diyne units as bridges. The tetrayne derivative 5c has been structurally characterized by single crystal X-ray crystallographic data. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

  (Z)-1,4-二乙炔基-1,4-二甲氧基环己-2,5-二烯已被用作合成两种含有buta-1,3-diyne 单元作为桥梁的新型大环的结构单元。四炔衍生物 5c 已通过单晶 X 射线晶体学数据在结构上进行了表征。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)