1,5-diselenocyanatopentane | 195969-08-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 1,5-diselenocyanatopentane
• 英文别名: 5-Selenocyanatopentyl selenocyanate
• CAS: 195969-08-5
• 化学式: C₇H₁₀N₂Se₂
• 分子量: 280.09
• InChiKey: RRLADTPWRMFMRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.36
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,5-diselenocyanatopentane 在 sodium hydroxide 、 正丁基锂 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 4.0h， 生成 1,4,9,12-tetraselenacycloheptadeca-2,10-diyne
  参考文献：
  名称：

  Cyclic Tetraselenadiynes:  Rigid Cycles with Long-Range van der Waals Forces between Chalcogen Centers

  摘要：

  The synthesis of cyclic tetraselenadiynes could be achieved by a stepwise approach. Key steps were the reaction of the lithium salt of trimethylsilylacetylene (1) with alpha,w-diselenocyanatoalkanes 2(m) (m = 2-5). By treating the bis-lithium salt of the resulting alpha,w-diselenaalkadiynes 4(m) (m = 2-5) again with 2(n) (n = 2-5) the cyclic tetraselenadiynes 5(m.n) resulted, with methylene chains of length m and n between the SeCequivalent toCSe units. The structures of seven ring systems could be investigated in the solid state. These investigations reveal that the molecular structures are determined by the rigid SeCequivalent toCSe units, which try to adopt torsion angles of the CH2-Se sigma-bonds between 60degrees and 90degrees. In the solid state, the systems 5(3.3) and 5(5.5) show columnar structures that can be traced back to close contacts between Se atoms of neighboring rings.

  DOI：

  10.1021/jo020014i
• 作为产物：
  描述：

  1,5-二溴戊烷 、 alkaline earth salt of/the/ methylsulfuric acid 在 丙酮 作用下， 生成 1,5-diselenocyanatopentane
  参考文献：
  名称：

  Morgan; Burstall, Journal of the Chemical Society, 1929, p. 2202

  摘要：

  DOI：

文献信息

• Syntheses and solid state structures of cyclic diynes with two chalcogen centres ? a competition between weak interactions
  作者：J. Hilko Schulte、Daniel B. Werz、Frank Rominger、Rolf Gleiter

  DOI：10.1039/b303653g

  日期：——

  Structural investigations by means of X-ray diffraction reveal for most systems a chair-like conformation in the solid state. For 5S(2)2, 5S(2)3, 7S(2)5, 5Se(2)2 and 5Te(2)3 tubular structures were encountered. These structures can be traced back to weak XX or weak C-Hpi interactions.

  在本文中，我们报告了通式为mX2n的环状二炔的合成。字母m和n表示两个C三键CX单元之间的链长，其中X表示S，Se或Te。桥的长度在m = 4-8和n = 2-6之间变化。通过X射线衍射进行的结构研究表明，对于大多数系统而言，固态呈椅子状构象。对于5S（2）2、5S（2）3、7S（2）5、5Se（2）2和5Te（2）3，遇到管状结构。这些结构可以追溯到弱XX或弱C-Hpi相互作用。
• Cyclic Tetra- and Hexaynes Containing 1,4-Donor-Substituted Butadiyne Units:  Synthesis and Supramolecular Organization
  作者：Daniel B. Werz、Rolf Gleiter、Frank Rominger

  DOI：10.1021/jo035882+

  日期：2004.4.1

  the cyclic dimers (S, 2(n); Se, 9(n)) or the cyclic trimers (S, 8(n); Se, 10(n)). Most of the molecular structures of 2(n) and 9(n) adopt chairlike conformations in the solid state. Tubular structures in the solid state with short distances between the chalcogen centers of neighboring stacks were encountered for 2(5), 9(5), 8(4), 10(4), and 10(5). Recrystallization of 10(5) from various polar and nonpolar

  硫的中心位于1,3-丁二炔单元（2（n））的α-位的环状双（1,3-丁二炔）是通过相应的开链二硫-α，ω-二炔1的Glaser偶联合成的（n）。在第二种方案中，我们通过使α，ω-二硫代氰基链烷烃6（n）或α，ω-二硒代氰基链烷烃7（n）与1,3,3-丁二酰亚胺二锂反应进行了四组分环化。该概念提供了环状二聚体（S，2（n）； Se，9（n））或环状三聚体（S，8（n）； Se，10（n））。2（n）和9（n）的大多数分子结构在固态时采用椅子状构型。对于2（5），9（5），8（4），10（4）和10（5），遇到了在相邻烟囱的硫族元素中心之间具有短距离的固态管状结构。从各种极性和非极性溶剂中重结晶10（5）会产生溶剂客体分子的内含物。溶剂可及体积计算，以改变从19％（正-己烷），25％（均三甲苯）。我们循环的弹性特性是由于柔性亚甲基链和刚性1,3-丁二炔棒之间容易改变的扭转角所致。
• Effects of Alkane Linker Length and Chalcogen Character in [FeFe]-Hydrogenase Inspired Compounds
  作者：Mohammad K. Harb、Ahmad Daraosheh、Helmar Görls、Elliott R. Smith、G. Joel Meyer、Matthew T. Swenson、Takahiro Sakamoto、Richard S. Glass、Dennis L. Lichtenberger、Dennis H. Evans、Mohammad El-khateeb、Wolfgang Weigand

  DOI：10.1002/hc.21216

  日期：2014.11

  these five compounds are not significantly affected by chalcogen character but instead are governed by linker length. Cations for all compounds are calculated to adopt a bridged CO “rotated” structure with a vacant site on one of the Fe centers. In 4DT, 4DS, and 5DS, the alkane linker forms an agostic interaction with the vacant site on the rotated Fe. The reduction potentials for these compounds shift

  已经制备了含有不同桥接头长度的二硒化配体的 [FeFe]-氢化酶模型：Fe2(μ-Se(CH2)4Se-μ)(CO)6 (4DS) 和 Fe2(μ-Se( )5Se- μ)(CO)6 (5DS) 以及二硫醇合 Fe2(μ-S( )4S-μ)(CO)6 (4DT) 并与 Fe2(μ-S( )3S-μ)(CO) 进行比较6 (PDT) 和 Fe2(μ-Se( )3Se-μ)(CO)6 (PDS)。化合物 4DT、PDS、4DS 和 5DS 通过光谱技术进行表征，包括 NMR、IR、质谱、紫外光电子能谱 (UPS)、元素分析和 X 射线晶体结构分析。电化学测量、UPS 和密度泛函理论计算的组合表明，这五种化合物的氧化不受硫属元素特征的显着影响，而是受接头长度的控制。所有化合物的阳离子都被计算为采用桥接的 CO“旋转”结构，在其中一个 Fe 中心上有一个空位。在 4DT、4DS 和
• Macrocyclic Cyclophanes with Two and Three α,ω-Dichalcogena-1,4-diethynylaryl Units: Syntheses and Structural Properties
  作者：Daniel B. Werz、Felix R. Fischer、Stefan C. Kornmayer、Frank Rominger、Rolf Gleiter

  DOI：10.1021/jo801378p

  日期：2008.10.17

  By means of four- and six-component cyclization reaction various cyclophanes were synthesized. The components were the di(lithium) salts of 1,4-di(ethynyl)benzene (11), 4,4'-di(ethynyl)biphenyl (13), 1,4-di(ethynyl)-2,5-di(n-hexyl)benzene (18), and 1,4-di(ethynyl)-2,5-di(n-propyl)benzene (19). These building blocks were reacted with alpha,omega-dithiocyanato-n-alkanes and alpha,omega-diselenocyanato-n-alkanes with n = 3-6. In the case of 10 also 1,1'-di(2-thiocyanatoethyl)cyclohexane (24) was reacted to afford a cyclophane comprising three subunits of 11. From most of the resulting macrocyclic cyclophanes (4(n) (n = 3, 5), 5, 6, 7(n), 8(n) (n = 3-6), 9(n) (n = 3, 5), and 10), we were able to grow single crystals. The X-ray analysis of 4(3), 7(3), 8(3), 8(4), 6, 7(5), and 8(5) revealed close contacts between the chalcogen atoms. These chalcogen-chalcogen interactions impose a ribbon-shape arrangement of molecules in 4(3) and a mutual crossing of two perdendicular planes built of 8(4) molecules. For 4(3) we found a close contact (3.28 angstrom) between the pi planes of two neighboring C6H4 rings of different molecules, whereas in 8(4) such a close contact (3.74 angstrom) was due to an intermolecular interaction. Tubular stacking of the macrocyclic rings was found for 7(5) and 8(5) caused by a ladder-type intermolecular chalcogen-chalcogen interaction.
• Nanotube Formation Favored by Chalcogen−Chalcogen Interactions
  作者：Daniel B. Werz、Rolf Gleiter、Frank Rominger

  DOI：10.1021/ja027146d

  日期：2002.9.1

  Close contacts between sulfur, selenium, and tellurium centers are used to construct nanotubes in the solid state which are able to host other molecules.