2-(4-{Cyano-[2-(4-methoxy-phenyl)-3,3aλ⁴-dithia-3b-aza-cyclopenta[a]inden-8-yl]-methylene}-cyclohexa-2,5-dienylidene)-malononitrile | 141511-49-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(4-{Cyano-[2-(4-methoxy-phenyl)-3,3aλ⁴-dithia-3b-aza-cyclopenta[a]inden-8-yl]-methylene}-cyclohexa-2,5-dienylidene)-malononitrile
• 英文别名: 2-[4-[cyano-[4-(4-methoxyphenyl)-2λ4,3-dithia-1-azatricyclo[6.4.0.02,6]dodeca-2(6),4,7,9,11-pentaen-7-yl]methylidene]cyclohexa-2,5-dien-1-ylidene]propanedinitrile
• CAS: 141511-49-1
• 化学式: C₂₇H₁₆N₄OS₂
• 分子量: 476.582
• InChiKey: YBTRAUCTCVKDSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.28
• 重原子数：
  34
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  128
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-[5-(4-Methoxy-phenyl)-[1,2]dithiol-(3Z)-ylidenemethyl]-pyridine 在 7,7,8,8-四氰基对苯二醌二甲烷 作用下， 以 乙腈 为溶剂， 以13%的产率得到2-(4-{Cyano-[2-(4-methoxy-phenyl)-3,3aλ⁴-dithia-3b-aza-cyclopenta[a]inden-8-yl]-methylene}-cyclohexa-2,5-dienylidene)-malononitrile
  参考文献：
  名称：

  (Pyridinylmethylidene)dithioles: synthesis, structure, and reactivity

  摘要：

  Spectral characteristics, an X-ray crystal structure, and molecular orbital calculations indicate that (pyridinylmethylidene)dithioles 3, prepared from butadiynyl precursors 4 and hydrogen sulfide in basic methanol, are analogous in their bonding to the parent 1-aza-6,6a-lambda-4-dithiapentalenes 1 which, according to ab initio studies at the Hartree-Fock level, is best represented as an (iminomethylidene)dithiole. An interaction between the sulfur and the nitrogen atoms is evident from the significant polarization of the S-S bond in those isomers where the nitrogen is proximal to the dithiole moiety. A comparison of the calculated structures of 1 and 3 with experimental data, as well as preliminary calculations on the related system trithiapentalene 2, suggest that ab initio methods using a single determinant are inadequate to describe these hypervalent sulfur systems. For example, an asymmetric structure is calculated to be the minimum energy form for 2 in contradiction to experimental results. Electrophilic substitutions, ring rearrangement, and reaction with electron acceptors are described for 3.

  DOI：

  10.1021/jo00040a032