1,3-di-tert-butylcyclopentadiene | 73046-16-9

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 1,3-di-tert-butylcyclopentadiene
• 英文别名: 1,3-Cyclopentadiene,1,3-bis(1,1-dimethylethyl)-；1,3-ditert-butylcyclopenta-1,3-diene
• CAS: 73046-16-9
• 化学式: C₁₃H₂₂
• 分子量: 178.318
• InChiKey: YDQHBVMPIFXJPJ-UHFFFAOYSA-N

物化性质

• 熔点：
  117-121 °C(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,3-di-tert-butylcyclopentadiene 在 二氯化二硫 、 甲基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 0.25h， 以44%的产率得到bis(2,4-di-tert-butyl-1,3-cyclopentadieny-1-yl)disulfane
  参考文献：
  名称：

  Synthesis and Structure of Bis(2,4‐di‐ tert ‐butyl‐1,3‐cyclopentadien‐1‐yl)‐disulfane, S ₂ ( t Bu ₂ C ₅ H ₃ ) ₂ , and Bis[2,4‐di‐ tert ‐butyl‐5‐(trimethylsilyl)‐1,3‐cyclopentadien‐1‐yl]disulfane, S ₂ [ t Bu ₂ (Me ₃ Si)C ₅ H ₂ ] ₂

  摘要：

  AbstractReaction of 1,3‐di‐tert‐butylcyclopentadienyllithium and 1,3‐di‐tert‐butyl‐4‐(trimethylsilyl)cyclopentadienyllithium with S2Cl2 gives bis(2,4‐di‐tert‐butyl‐1,3‐cyclopentadien‐1‐yl)di‐sulfane (1) and bis[2,4‐di‐tert‐butyl‐5‐(trimethylsilyl)‐1,3‐cyclopentadien‐1‐yl) disulfane (2), respectively. The structure of 2 was determined by single‐crystal X‐ray diffraction. Compounds 1 and 2 are the first biscyclopentadienylchalcogens with the chalcogen in vinylic position.

  DOI：

  10.1002/cber.19961290114
• 作为产物：
  描述：

  溴代叔丁烷 、 环戊二烯 在 18-冠醚-6 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以43%的产率得到1,3-di-tert-butylcyclopentadiene
  参考文献：
  名称：

  Rational Synthesis of Metallo-Cations Toward Redox- and Alkaline-Stable Metallo-Polyelectrolytes

  摘要：

  Cations are crucial components in emerging functional polyelectrolytes for a myriad of applications. Rapid development in this area necessitates the exploration of new cations with advanced properties. Herein we describe a combination of computational and experimental design of cobaltocene metallo-cations that have distinct electronic and redox properties. One of the direct outcomes on the first synthesis of a complete set of cation derivatives is to discover highly stable cations, which are further integrated to construct metallo-polyelectrolytes as anion-exchange membranes in solid-state alkaline fuel cells. The device performance of these polyelectrolytes under highly basic and oxidative environments is competitive with many organo-polyelectrolytes.

  DOI：

  10.1021/jacs.9b12051

文献信息

• Synthesis and properties of sterically congested cyclopentadienes and their transition metal complexes
  作者：T.Jeffrey Clark、Christopher M. Killian、Sanjay Luthra、Terence A. Nile

  DOI：10.1016/0022-328x(93)83365-3

  日期：1993.12

  The synthesis of 1,3-dialkyl substituted cyclopentadienes, C5H4RR′, Cp′H (Va–g) (where R and R′ are tert-butyl, iso-propyl, neo-pentyl, cyclohexyl, or 1-methylcyclohexyl) is reported. These are synthesized by the nucleophilic addition of methyl or hydride anions to the corresponding 2-alkyl-6,6-dialkylfulvenes (IIIa–f) followed by hydrolysis. These substituted 1,3-cyclopentadienes have been converted

  1,3-二烷基取代的环戊二烯，C 5 H 4 RR'，Cp'H（Va–g）（其中R和R'为叔丁基，异丙基，新戊基，环己基或1-甲基环己基）。这些是通过将甲基或氢化物阴离子亲核加成到相应的2-烷基-6,6-二烷基富勒烯（IIIa–f）中，然后水解而合成的。这些取代的1,3-环戊二烯已转化为有机金属衍生物例如[CP'Fe（CO）2 ] 2，[CP'M（CO）3本人]（MMo或W）和CP' 22Fe。为了研究取代的环戊二烯基配体的空间和电子性质，已经研究了所选配合物的光谱和电化学性质。
• Synthesis and Properties of Diruthenium Tetrahydrides Supported by Less-substituted, Sterically Demanding Poly-<i>tert</i>-butylated Cyclopentadienyls
  作者：Takako Yanagi、Hiroharu Suzuki、Masataka Oishi

  DOI：10.1246/cl.130699

  日期：2013.11.5

  Synthesis of diruthenium tetrahydrido complexes 1 with substituted cyclopentadienyls from readily available ruthenium η3-allyl complexes 3 has been attained by LiEt3BH-mediated reaction followed by conventional protonolysis. Complexes 1d and 1e having 1,2,4-tri- and 1,3-di-tert-butylated cyclopentadienyls obtained by this protocol have sufficient thermal stability in addition to the significant lability of the Ru–H bonds.

  通过LiEt3BH介导的反应，随后进行常规的质子解离，成功合成了与已知的环戊二烯基取代基相结合的二铑四氢化合物1，这些取代基来源于易得的铑η3-烯丙基化合物3。采用该方法合成的复合物1d和1e含有1,2,4-三和1,3-二叔丁基环戊二烯基，不仅具有足够的热稳定性，还显示了Ru–H键的显著活泼性。
• Enhancement of Push-Pull Properties of Pentafulvene and Pentafulvalene Derivatives by Protonation at Carbon
  作者：Sophie Haberland、Aaron D. Finke、Nicolas Kerisit、Claudine Katan、Yann Trolez、Przemyslaw Gawel、Ivo Leito、Märt Lõkov、Robert Järviste、Karl Kaupmees、Nils Trapp、Laurent Ruhlmann、Corinne Boudon、Daniel Himmel、François Diederich

  DOI：10.1002/ejoc.201800039

  日期：2018.2.14

  We report visible color changes and new intense, bathochromically shifted bands in electronic absorption spectra that reach into the near-infrared region (up to 862 nm) upon protonation of nine pentafulvene and expanded pentafulvalene derivatives. This phenomenon can only be explained by the formation of carbocations with highly delocalized charges. Solution pKa values in organic solvents were determined

  我们报告了在九个五富烯和扩展的五富瓦烯衍生物质子化后进入近红外区域（高达 862 nm）的电子吸收光谱中的可见颜色变化和新的强烈、红移带。这种现象只能通过形成具有高度离域电荷的碳正离子来解释。使用相对碱度测量方法测定有机溶剂中的溶液 pKa 值。所有七个
• Reactions of di- and tri- tert -butylcyclopentadienes with dihalocarbenes
  作者：Eckehard V. Dehmlow、Christof Bollmann

  DOI：10.1016/0040-4020(95)00119-s

  日期：1995.3

  Dihalocarbene additions to mixed 1,3- and 1,4-di-tert-butylcyclopentadienes (1, 3) allow to prepare 1,3-di-tert-butyl-4-halobenzenes (9) in an efficient way. Only the 3,4 double bond is attacked regiospecifically in 1,3,5-tri-tert-butylcyclopentadiene (11) (and also in 1).Totally unexpected main products from 11 are compounds 9 again being formed under fragmentation of a tert-butyl group. Only small

  二卤卡宾补充混合1,3-和1,4-二-叔butylcyclopentadienes（1,3）允许以制备1,3-二-叔丁基-4-卤代苯（9以有效的方式）。在1,3,5-三叔丁基环戊二烯（11）中（以及也在1中）只有3,4双键被区域特异性攻击。从11中完全出乎意料的主要产物是化合物9在叔-叔丁基的断裂下再次形成丁基。只的1,2,4-三-帐篷丁基S-卤代苯（少量13，X =氯，溴）从获得的11。11（12a）不稳定的初级二氯卡宾加合物可以隔离。其热分解发生，失去一个叔丁基基团，生成9a。碱催化的12a降解产生副产物9a和13a。
• Di-tert-butylcyclopentadiene and tri-tert-butylcyclopentadiene
  作者：Clifford G. Venier、Edward W. Casserly

  DOI：10.1021/ja00163a057

  日期：1990.3

  Synthese de tris-t-butyl-1,2,4 et de di-t-butyl-1,3 (1,4 ou 2,5) cyclopentadiene-1,3 par alkylation, avec catalyse transfert phase, de cyclopentadiene-1,3 avec le bromo-2 methyl-2 propane

  合成 de tris-t-butyl-1,2,4 和 de di-t-butyl-1,3 (1,4 ou 2,5) cyclopentadiene-1,3 对烷基化，avec 催化转移相，de cyclopentadiene-1 ,3 avec le bromo-2methyl-2 丙烷