1,5-bis(triethylsilyl)penta-1,4-diyn-3-ol | 1198424-84-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,5-bis(triethylsilyl)penta-1,4-diyn-3-ol
• 英文别名: 1,5-bis-TES-penta-1,4-diyne-3-ol
• CAS: 1198424-84-8
• 化学式: C₁₇H₃₂OSi₂
• 分子量: 308.611
• InChiKey: YTTOJMWFNLWSAP-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：
  8
• 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(triethylsilyl)penta-1,4-diyn-3-ol 在 barium manganate 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到1,5-bis-TES-penta-1,4-diyne-3-one
  参考文献：
  名称：

  级联反应形成高度取代的共轭磷脂和1,2-氧杂磷

  摘要：

  不仅仅是碳原子的复制：磷化氢-维蒂希-霍纳试剂与二乙炔酮的反应（参见方案）导致一系列反应，这些反应可同时导致以草磷化氢为末端的枯烯系统和烯烃桥联的双磷化氢。反应结果由乙炔末端的性质决定，苯基可稳定卡宾中间体，该中间体二聚化生成双磷产物。

  DOI：

  10.1002/anie.201202153
• 作为产物：
  描述：

  三乙基矽乙炔 、 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76%的产率得到1,5-bis(triethylsilyl)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5c-f. The title compounds represent rare examples of diethynylethenes in which a constituting methylene has been replaced by a phosphorus center.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

• [EN] METHODS OF MAKING MULTICYCLIC COMPOUNDS USING MULTICOMPONENT/TANDEM REACTION SEQUENCES<br/>[FR] PROCÉDÉS DE FABRICATION DE COMPOSÉS POLYCYCLIQUES À L'AIDE DE SÉQUENCES DE RÉACTION EN TANDEM/À PLUSIEURS COMPOSANTS
  申请人：UNIV NEVADA RENO

  公开号：WO2016153906A1

  公开（公告）日：2016-09-29

  Disclosed herein are embodiments of multicyclic compounds and methods of making such compounds. The disclosed methods reduce step-counts in the synthesis of complex targets, while reducing costs and waste streams.

  本文公开了多环化合物的实施例以及制备这些化合物的方法。所公开的方法可以减少复杂目标合成中的步骤数量，同时降低成本和废物排放。
• <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.
• Cascade Reactions Forming Highly Substituted, Conjugated Phospholes and 1,2-Oxaphospholes
  作者：Anna I. Arkhypchuk、Marie-Pierre Santoni、Sascha Ott

  DOI：10.1002/anie.201202153

  日期：2012.7.27

  copy: The reaction of a phospha‐Wittig–Horner reagent with diacetylenic ketones (see scheme) results in a cascade of reactions that can lead to both an oxaphosphole‐terminated cumulene system and an alkene‐bridged bis‐phosphole. The reaction outcome is determined by the nature of the acetylene termini, with phenyl groups stabilizing a carbene intermediate that dimerizes to give the bis‐phosphole product

  不仅仅是碳原子的复制：磷化氢-维蒂希-霍纳试剂与二乙炔酮的反应（参见方案）导致一系列反应，这些反应可同时导致以草磷化氢为末端的枯烯系统和烯烃桥联的双磷化氢。反应结果由乙炔末端的性质决定，苯基可稳定卡宾中间体，该中间体二聚化生成双磷产物。