1,5-bis(tert-butyldimethylsilyl)penta-1,4-diyn-3-ol | 887586-57-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,5-bis(tert-butyldimethylsilyl)penta-1,4-diyn-3-ol
• 英文别名: 1,5-Di(tert-butyldimethylsilyl)-1,4-pentadiyn-3-ol；1,5-bis[tert-butyl(dimethyl)silyl]penta-1,4-diyn-3-ol
• CAS: 887586-57-4
• 化学式: C₁₇H₃₂OSi₂
• 分子量: 308.611
• InChiKey: QATCOSNLBIVJCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.45
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,5-bis(tert-butyldimethylsilyl)penta-1,4-diyn-3-ol 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 生成 、 1,5-bis(tert-butyldimethylsilyl)-3-chloropenta-1,4-diyne
  参考文献：
  名称：

  C,C-Diacetylenic Phosphaalkenes as Heavy Diethynylethene Analogues

  摘要：

  A series of C,C-diacetylenic phosphaalkenes 1b-e has been prepared from 1-chloropenta-1,2-dien-4-ynes 6b-e in a reaction with Mes*PCl2 (Mes* = 2,4,6-(Bu-1)(3)Ph) in the presence of LDA. Under identical conditions, isomeric butadiyne-substituted phosphaalkenes 2e-f can be obtained from 3-chloropenta-1,4-diyiies 5c-f. The title compounds represent rare examples of diethynylethenes in which a constituting methylene has been replaced by a phosphorus center. The formation of both isomers can be rationalized by a common pathway that involves isomeric allenyllithium species. Spectroscopic, electrochemical, and theoretical investigations show that the phosphorus heteroatoms are an intrinsic part of the compounds' pi-systems and lead to decreased HOMO-LUMO gaps compared to those in all-carbon-based reference compounds.

  DOI：

  10.1021/jo901942u
• 作为产物：
  描述：

  (叔丁基二甲基)乙炔 、 甲酸乙酯 在 正丁基锂 、 盐酸 、 氯化铵 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 2.25h， 以66%的产率得到1,5-bis(tert-butyldimethylsilyl)penta-1,4-diyn-3-ol
  参考文献：
  名称：

  C,C-Diacetylenic Phosphaalkenes as Heavy Diethynylethene Analogues

  摘要：

  A series of C,C-diacetylenic phosphaalkenes 1b-e has been prepared from 1-chloropenta-1,2-dien-4-ynes 6b-e in a reaction with Mes*PCl2 (Mes* = 2,4,6-(Bu-1)(3)Ph) in the presence of LDA. Under identical conditions, isomeric butadiyne-substituted phosphaalkenes 2e-f can be obtained from 3-chloropenta-1,4-diyiies 5c-f. The title compounds represent rare examples of diethynylethenes in which a constituting methylene has been replaced by a phosphorus center. The formation of both isomers can be rationalized by a common pathway that involves isomeric allenyllithium species. Spectroscopic, electrochemical, and theoretical investigations show that the phosphorus heteroatoms are an intrinsic part of the compounds' pi-systems and lead to decreased HOMO-LUMO gaps compared to those in all-carbon-based reference compounds.

  DOI：

  10.1021/jo901942u

文献信息

• <i>C</i>,<i>C</i>-Diacetylenic Phosphaalkenes as Heavy Diethynylethene Analogues
  作者：Elisabet Öberg、Bernhard Schäfer、Xue-Li Geng、Jenny Pettersson、Qi Hu、Mikael Kritikos、Torben Rasmussen、Sascha Ott

  DOI：10.1021/jo901942u

  日期：2009.12.18

  A series of C,C-diacetylenic phosphaalkenes 1b-e has been prepared from 1-chloropenta-1,2-dien-4-ynes 6b-e in a reaction with Mes*PCl2 (Mes* = 2,4,6-(Bu-1)(3)Ph) in the presence of LDA. Under identical conditions, isomeric butadiyne-substituted phosphaalkenes 2e-f can be obtained from 3-chloropenta-1,4-diyiies 5c-f. The title compounds represent rare examples of diethynylethenes in which a constituting methylene has been replaced by a phosphorus center. The formation of both isomers can be rationalized by a common pathway that involves isomeric allenyllithium species. Spectroscopic, electrochemical, and theoretical investigations show that the phosphorus heteroatoms are an intrinsic part of the compounds' pi-systems and lead to decreased HOMO-LUMO gaps compared to those in all-carbon-based reference compounds.