1,4,10,13-tetraselenacyclooctadeca-2,11-diyne | 402751-42-2

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 1,4,10,13-tetraselenacyclooctadeca-2,11-diyne
• CAS: 402751-42-2
• 化学式: C₁₄H₂₀Se₄
• 分子量: 504.153
• InChiKey: LWPOKUSMNLYELC-UHFFFAOYSA-N

物化性质

• 沸点：
  525.7±60.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  sodium trichloroacetate 、 1,4,10,13-tetraselenacyclooctadeca-2,11-diyne 以 乙二醇二甲醚 为溶剂， 反应 2.0h， 以7%的产率得到1,1',7,7'-tetraselena[7,7]cyclopropenophane
  参考文献：
  名称：

  Selenium- and Tellurium-Substituted Cyclopropenones and their Facile Ring-Opening with Methanol

  摘要：

  Treatment of donor-substituted acetylenes (X-CdropC-X, with X = R-Se, R-Te) with sodium trichloroacetate, followed by hydrolysis, yielded the corresponding cyclopropenones. Their structures could be elucidated by X-ray analysis, and indicated significant overlap between the p-type lone pairs on the chalcogen atoms and the cyclopropenone unit. DFT calculations were carried out on various conformers in order to clarify their relative energy profiles. Methanolysis of these ring systems at room temperature quantitatively afforded alpha,beta-unsaturated esters. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).

  DOI：

  10.1002/1099-0690(200301)2003:1<151::aid-ejoc151>3.0.co;2-7
• 作为产物：
  描述：

  1,11-bis(trimethylsilyl)-3,9-diselenaundeca-1,10-diyne 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 3.0h， 生成 1,4,10,13-tetraselenacyclooctadeca-2,11-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

文献信息

• Cyclic Tetraselenadiynes:  Rigid Cycles with Long-Range van der Waals Forces between Chalcogen Centers
  作者：Daniel B. Werz、Rolf Gleiter、Frank Rominger

  DOI：10.1021/jo020014i

  日期：2002.6.1

  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.
• Selenium- and Tellurium-Substituted Cyclopropenones and their Facile Ring-Opening with Methanol
  作者：Daniel B. Werz、Rolf Gleiter、Frank Rominger

  DOI：10.1002/1099-0690(200301)2003:1<151::aid-ejoc151>3.0.co;2-7

  日期：2003.1

  Treatment of donor-substituted acetylenes (X-CdropC-X, with X = R-Se, R-Te) with sodium trichloroacetate, followed by hydrolysis, yielded the corresponding cyclopropenones. Their structures could be elucidated by X-ray analysis, and indicated significant overlap between the p-type lone pairs on the chalcogen atoms and the cyclopropenone unit. DFT calculations were carried out on various conformers in order to clarify their relative energy profiles. Methanolysis of these ring systems at room temperature quantitatively afforded alpha,beta-unsaturated esters. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).