Spiro | 159791-36-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Spiro
• 英文别名: acenaphthenone ethylenedithioacetal；spiro[1,3-dithiolane-2,2'-1H-acenaphthylene]
• CAS: 159791-36-3
• 化学式: C₁₄H₁₂S₂
• 分子量: 244.381
• InChiKey: ASTFOTAHUDNDHP-UHFFFAOYSA-N

物化性质

• 沸点：
  449.1±45.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Spiro 在 四氯化碲 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 Acenaphtho<1,2-b><1,4>dithiine
  参考文献：
  名称：

  7,10-二硫代氟蒽及其阳离子自由基盐

  摘要：

  通过a庚烯酮乙二硫缩醛的扩环反应，由a庚烯酮分三步制备了第一个7,10-二硫代氟代蒽。它被证明是良好的π供体和形式高传导阳离子自由基盐，与PF 6 - 。盐的X射线晶体学分析显示供体的柱状堆叠结构，并且盐在室温下显示出高电导率。

  DOI：

  10.1016/0040-4039(94)88223-1
• 作为产物：
  描述：

  1-羟基二氢苊 在 铬酸 、 对甲苯磺酸 作用下， 以 乙醇 、 二氯甲烷 、 苯 为溶剂， 反应 12.08h， 生成 Spiro
  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

• 7,10-dithiafluoroanthene and its cation radical salt
  作者：Hiroyuki Tani、Yoshihiro Kawada、Nagao Azuma、Noboru Ono

  DOI：10.1016/0040-4039(94)88223-1

  日期：1994.9

  The first 7,10-Dithiafluoroanthene has been prepared from acenaphthenone in three steps, via ring expansion reaction of acenaphthenone ethylenedithioacetal. It was shown to be good π-donor and form highly conducting cation radical salts with PF6−. X-ray crystallographic analysis of the salt showed columnar stack structure of donors and the salt showed high electrical conductivity at room temperature

  通过a庚烯酮乙二硫缩醛的扩环反应，由a庚烯酮分三步制备了第一个7,10-二硫代氟代蒽。它被证明是良好的π供体和形式高传导阳离子自由基盐，与PF 6 - 。盐的X射线晶体学分析显示供体的柱状堆叠结构，并且盐在室温下显示出高电导率。
• Hiroyuki Tani, Yoshihiro Kawada, Nagao Azuma, Noboru Ono, Tetrahedron Lett, 35 (1994) N 38, S 7051- 7054
  作者：Hiroyuki Tani, Yoshihiro Kawada, Nagao Azuma, Noboru Ono

  DOI：——

  日期：——
• 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.