Spiro[acenaphthene-1,2'-(1',3'-dithiolane)]-2-one | 183595-87-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Spiro[acenaphthene-1,2'-(1',3'-dithiolane)]-2-one
• 英文别名: Spiro[1,3-dithiolane-2,2'-acenaphthen-1'-one]；spiro[1,3-dithiolane-2,2'-acenaphthylene]-1'-one
• CAS: 183595-87-1
• 化学式: C₁₄H₁₀OS₂
• 分子量: 258.365
• InChiKey: ZUMUDDCGRVHQEJ-UHFFFAOYSA-N

物化性质

• 沸点：
  485.7±45.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Spiro[acenaphthene-1,2'-(1',3'-dithiolane)]-2-one 在 盐酸 、 manganese(IV) oxide 、 氢氧化钾 、 一水合肼 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 1.0h， 生成 Acenaphtho<1,2-b><1,4>dithiine
  参考文献：
  名称：

  New π-electron donor systems based on acenaphtho[1,2-b][1,4]dithiine

  摘要：

  Syntheses of the acenaphtho[1,2-b] [1,4] dithiine derivatives 12, 25 and 29 are reported. Cyclic voltammetric studies reveal that these compounds undergo reversible single-electron oxidations at < 1.0 V, vs. Ag/AgCl. Lithiation of compound 12 with BuLi (2 equiv.) followed by addition of either methyl iodide or ethyl chloroformate yielded the unstable ring-opened acetylene derivatives 22a and 22b, respectively. A new synthesis of 1,2-diselenine derivative 33 is reported. Compound 25 formed 1:1 charge-transfer complexes with 7,7,8,8-tetracyano-p-quinodimethane (TCNQ) and with 2,5-dibromo-TCNQ, both of which were electrical insulators. The X-ray crystal structures of compound 25, a charge-transfer complex 25:Br,TCNQ (1:1 stoichiometry) and compound 33 are reported. In the structure of 25:Br,TCNQ, molecules of 25 and Br,TCNQ form mixed stacks. The folding of the donor along the S ... S vector in the complex is 17 degrees (ef. 48 degrees in pure 25) and the conformation of 25 is discussed in the light of previous studies on 1,4-dithiine derivatives. An interesting feature of the crystal structure of 33 is the formation of pseudo-dimers with two short intermolecular Se Se contacts.

  DOI：

  10.1039/p19960002451
• 作为产物：
  描述：

  1,2-乙二硫醇 、 苊醌 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 2.0h， 以73%的产率得到Spiro[acenaphthene-1,2'-(1',3'-dithiolane)]-2-one
  参考文献：
  名称：

  New π-electron donor systems based on acenaphtho[1,2-b][1,4]dithiine

  摘要：

  Syntheses of the acenaphtho[1,2-b] [1,4] dithiine derivatives 12, 25 and 29 are reported. Cyclic voltammetric studies reveal that these compounds undergo reversible single-electron oxidations at < 1.0 V, vs. Ag/AgCl. Lithiation of compound 12 with BuLi (2 equiv.) followed by addition of either methyl iodide or ethyl chloroformate yielded the unstable ring-opened acetylene derivatives 22a and 22b, respectively. A new synthesis of 1,2-diselenine derivative 33 is reported. Compound 25 formed 1:1 charge-transfer complexes with 7,7,8,8-tetracyano-p-quinodimethane (TCNQ) and with 2,5-dibromo-TCNQ, both of which were electrical insulators. The X-ray crystal structures of compound 25, a charge-transfer complex 25:Br,TCNQ (1:1 stoichiometry) and compound 33 are reported. In the structure of 25:Br,TCNQ, molecules of 25 and Br,TCNQ form mixed stacks. The folding of the donor along the S ... S vector in the complex is 17 degrees (ef. 48 degrees in pure 25) and the conformation of 25 is discussed in the light of previous studies on 1,4-dithiine derivatives. An interesting feature of the crystal structure of 33 is the formation of pseudo-dimers with two short intermolecular Se Se contacts.

  DOI：

  10.1039/p19960002451

文献信息

• New π-electron donor systems based on acenaphtho[1,2-b][1,4]dithiine
  作者：Martin R. Bryce、Antony Chesney、Alexander K. Lay、Andrei S. Batsanov、Judith A. K. Howard

  DOI：10.1039/p19960002451

  日期：——

  Syntheses of the acenaphtho[1,2-b] [1,4] dithiine derivatives 12, 25 and 29 are reported. Cyclic voltammetric studies reveal that these compounds undergo reversible single-electron oxidations at < 1.0 V, vs. Ag/AgCl. Lithiation of compound 12 with BuLi (2 equiv.) followed by addition of either methyl iodide or ethyl chloroformate yielded the unstable ring-opened acetylene derivatives 22a and 22b, respectively. A new synthesis of 1,2-diselenine derivative 33 is reported. Compound 25 formed 1:1 charge-transfer complexes with 7,7,8,8-tetracyano-p-quinodimethane (TCNQ) and with 2,5-dibromo-TCNQ, both of which were electrical insulators. The X-ray crystal structures of compound 25, a charge-transfer complex 25:Br,TCNQ (1:1 stoichiometry) and compound 33 are reported. In the structure of 25:Br,TCNQ, molecules of 25 and Br,TCNQ form mixed stacks. The folding of the donor along the S ... S vector in the complex is 17 degrees (ef. 48 degrees in pure 25) and the conformation of 25 is discussed in the light of previous studies on 1,4-dithiine derivatives. An interesting feature of the crystal structure of 33 is the formation of pseudo-dimers with two short intermolecular Se Se contacts.