cis-1,2-bis-(methylmercapto)-1,2-dicyanoethylene | 7373-02-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: cis-1,2-bis-(methylmercapto)-1,2-dicyanoethylene
• 英文别名: cis-1,2-di(methylmercapto)-1,2-dicyanoethylene；cis-1,2-dicyano-1,2-bis(methylthio)ethylene；2,3-di(methylsulfanyl)-2-butenedinitrile；1,2-dicyano-1,2-bis(methylthio)ethylene；2,3-bis(thiosulfanyl)but-2-enedinitrile；2,3-bis(methylsulfanyl)maleonitrile；(Z)-2,3-bis(methylsulfanyl)but-2-enedinitrile
• CAS: 7373-02-6
• 化学式: C₆H₆N₂S₂
• 分子量: 170.259
• InChiKey: JYGDGMIEJUMABD-WAYWQWQTSA-N

物化性质

• 熔点：
  99-99.5 °C
• 沸点：
  246.0±40.0 °C(Predicted)
• 密度：
  1.256±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  98.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cis-1,2-bis-(methylmercapto)-1,2-dicyanoethylene 在 硫酸 、 氧气 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 3,3'-dimethyl-2,2'-dithioxo-[5,5']bithiazolidinylidene-4,4'-dione
  参考文献：
  名称：

  Studies on Fungicides. XXV. Addition Reaction of Dithiocarbamates to Fumaronitrile, Bis (alkylthio) maleonitrile, 2, 3-Dicyano-5, 6-dihydro-1, 4-dithiin and 4, 5-Dicyano-2-oxo-1, 4-dithiole

  摘要：

  5-氰甲基-2-硫酮-4-氨基硫氮茂 (II) 可用富马睛与二硫代氨基甲酸盐的加成反应来制备。用二硫代氨基甲酸盐与双 (甲硫基) 马来睛 (IXa)，双 (苄硫基) 马来睛 (IXb)，2，3-二氰基-5，6-二氢-1，4-二硫茂 (IXc)及4，5-二氰基-2-氧-1，4-二硫茂 (IXd) 反应，制得了 5，5'-双-2-硫酮-4-氨基硫氮茂 (X)。发现 II 及 X 的 4-氨基对酸不稳定，与无机酸加热时，即水解而得 5-氰甲基-2-硫酮-4-硫氮杂茂酮 (III) 及 5，5'-双-2-硫酮-4-硫氮杂茂酮 (XII)。发现 X 于催化量的三乙胺存在时可自动氧化成 Δ 5，5'-双-2-硫酮-4-亚氨基硫氮茂 (XI)。由 N-苄基二硫代氨基甲酸盐与5-亚氰甲基-2-硫酮-4-硫氮杂茂酮 (XIV) 的加成反应制得了 4-氧-4，亚氨基-Δ5，5'-双-2-硫酮-硫氮杂茂酮 (XVI)。用无机酸水解 XI 及 XIV，制得了 Δ5，5'-双-2-硫酮-4-硫氮杂茂酮 (XIII)。

  DOI：

  10.1248/cpb.22.505
• 作为产物：
  描述：

  2,3-bis(thiosulfanyl)but-2-enedinitrile 以 甲醇 为溶剂， 反应 12.0h， 生成 cis-1,2-bis-(methylmercapto)-1,2-dicyanoethylene
  参考文献：
  名称：

  Thiacyanocarbons. II. Chemistry of Disodium Dimercaptomaleonitrile

  摘要：

  DOI：

  10.1021/ja00883a029

文献信息

• Highly Efficient One-Pot Synthesis of Metalloporphyrazines under Mild Conditions
  作者：L. Giribabu、M. Chandrasekharam、S. Mohan、Ch. Rao、M. Kantam、M. Reddy、P. Reddy、Takeshi Toru

  DOI：10.1055/s-2006-944186

  日期：2006.6

  for the first time by treatment with metal salts, hexamethyldisilazane (HMDS) and p-toluene sulfonic acid (PTSA) in DMF at 120 °C. This reaction provides a new preparative method under mild conditions for direct synthesis of metalloporphyrazines having a variety of metals and substituted maleonitriles.

  通过在 120 °C 的 DMF 中用金属盐、六甲基二硅氮烷 (HMDS) 和对甲苯磺酸 (PTSA) 处理，首次实现了从马来腈中制备游离碱和金属四氮杂卟啉的新型单步法。该反应为在温和条件下直接合成具有多种金属和取代马来腈的金属卟啉提供了一种新的制备方法。
• Unsymmetrical Pentoxy-Substituted Porphyrazines
  作者：I. Yu. Nikolaev、E. V. Kudrik、V. P. Kulinich、G. P. Shaposhnikov

  DOI：10.1007/s11176-005-0251-9

  日期：2005.3

  The reactions of 3,6-dipentoxyphthalonitrile (A) in the 1-pentanol - magnesium pentylate medium with phthalonitrile, 2,3-di(methylsulfanyl)-2-butenedinitrile, and 2,3-dihydro-1,4-dithiin-5,6-dicarbonitrile (B) were performed. Unsymmetrically substituted porphyrazines A3B were prepared and studied. The influence of the structure of fragment B on the spectral characteristics of the porphyrazines was examined.

  在 1-戊醇-戊酸镁介质中，3,6-二戊氧基邻苯二甲腈（A）与邻苯二甲腈、2,3-二（甲硫基）-2-丁烯二腈和 2,3-二氢-1,4-二硫杂-5,6-二甲腈（B）发生了反应。制备并研究了不对称取代的卟吩嗪 A3B。研究了片段 B 的结构对卟吩嗪类化合物光谱特性的影响。
• The reaction of alkyl halides with the bis(1,2-dicyanoethylenedithiolato)lead(II) ion
  作者：C.W. Allen、D.E. Lutes、E.J. Durhan、E.S. Bretschneider

  DOI：10.1016/s0020-1693(00)86274-x

  日期：1977.1

  Abstract The reaction of the bis(1,2-dicyanoethylenedithiolato)lead(II) ion, Pb(mnt) 2 − 2 , with various organohalides has been examined and found to yield the halo(1,2-dicyanoethylenedithiolato)lead(II) ion Pb(mnt)X − (X = Br, I) and the 1,2-di(alkylmercapto) 1,2-dicyanoethylene, R 2 mnt (R = 1°, 2° alkyl). Qualitative rate studies have shown that the alkylation proceeds much faster for Pb(mnt) −

  摘要研究了双（1,2-二氰基乙二硫代乙二酸铅）铅（II）离子Pb（mnt）2-2与各种有机卤化物的反应，发现可生成卤代（1,2-二氰基乙二硫基乙二酸）铅（II）。离子Pb（mnt）X-（X = Br，I）和1,2-二（烷基巯基）1,2-二氰基乙烯，R 2 mnt（R = 1°，2°烷基）。定性速率研究表明，Pb（mnt）-2的烷基化过程比Na 2 mnt的烷基化过程快得多。
• Baehr; Schleitzer, Chemische Berichte, 1957, vol. 90, p. 438,443
  作者：Baehr、Schleitzer

  DOI：——

  日期：——
• Surface-Bound Porphyrazines:  Controlling Reduction Potentials of Self-Assembled Monolayers through Molecular Proximity/Orientation to a Metal Surface
  作者：Benjamin J. Vesper、Khalid Salaita、Hong Zong、Chad A. Mirkin、Anthony G. M. Barrett、Brian M. Hoffman

  DOI：10.1021/ja045270m

  日期：2004.12.1

  We report the preparation of two novel H-2[pz(A(n);B4-n)] porphyrazines (pzs) which were designed to position themselves quite differently when attached to a surface: one to form a standard self-assembled monolayer (SAM) roughly perpendicular to a surface, the other to lie horizontally along a surface. As the former, we synthesized a pz, 1, where one pyrrole group is functionalized with two thioethers terminated in mercaptides (SR, R = (CH2)(3)CONH(CH2)(2)S-), each protected as a disulfide, and -S-Me is attached to the other pyrrole sites; the latter is a pz, 2, with dialkoxybenzo groups fused to two trans-pyrroles of the pz ring, and SR groups are attached to the other pair of pyrroles. Nanostructures of 1 and 2 were successfully patterned on gold surfaces via dip-pen nanolithography, and the predicted molecular orientation of the resulting structures was confirmed by topographic AFM images. The two pzs exhibit similar reduction potentials in solution. Both show large shifts in potential upon surface binding, with the magnitude of the shift depending on the proximity/orientation of the pz to the surface. The first reduction potential of the "vertically" aligned 1 shifts by ca. +430 mV when incorporated in a binary pz/hexanethiol SAM, while that for 2, which lies flat, shifts by ca. +800 mV; the potential thus shifts by ca. +370 mV upon taking a given pz that stands atop a two-legged insulating "standoff" in a traditional SAM and "laying it down". We suggest these observed effects can be explained by image-charge energetics, and this is supported by a simple model.