4,5-diphenyl-1,2,3-selenadiazole | 27892-81-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,5-diphenyl-1,2,3-selenadiazole
• 英文别名: 4,5-diphenylselenadiazole
• CAS: 27892-81-5
• 化学式: C₁₄H₁₀N₂Se
• 分子量: 285.207
• InChiKey: XCDVPRVPYCYVKF-UHFFFAOYSA-N

物化性质

• 沸点：
  381.3±45.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,5-diphenyl-1,2,3-selenadiazole 在 cesium fluoride 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 生成 Dimethyl 1-{(E)-2-[(Z)-1,2-bis(methoxycarbonyl)vinylseleno]-1,2-diphenylethenyl}-1H-pyrazole-3,4-dicarboxylate
  参考文献：
  名称：

  Transformations of selenadiazoliumyl-N-unsubstituted methanides (ylides) to new divinyl selenide derivatives and substituted 1,3,5-selenadiazines. Organoselenium systems from azolium 1,3-dipoles

  摘要：

  4,5-二苯基-1,2,3-硒二唑和 3,5-二苯基-1,2,4-硒二唑被三氟甲磺酸三甲基硅甲基酯烷基化。季化合物分别发生在 N-3 和 N-2。盐类经脱硅烷化后生成瞬时硒二唑甲酰亚胺（酰亚胺）中间体。4,5-二苯基-1,2,3-硒二唑-3-鎓-3-甲烷化物 3 与乙炔二甲酸二甲酯和丙炔酸甲酯发生环化重排反应，生成吡唑乙烯基硒化物 6 和 7。3,5-二苯基-1,2,4-硒二唑-2-鎓-2-基甲烷化物 10 在原位环展生成 4,6-二苯基-2H-1,3,5-硒二嗪 13。

  DOI：

  10.1039/b007974j
• 作为产物：
  描述：

  1,2-diphenyl-ethanone semicarbazone 在 selenium(IV) oxide 、 溶剂黄146 作用下， 生成 4,5-diphenyl-1,2,3-selenadiazole
  参考文献：
  名称：

  某些芳基1,2,3-三硒二唑的合成及1 H核磁共振谱

  摘要：

  制备了一系列芳基1,2,3-3-硒代二唑，并记录了它们的核磁共振光谱参数。由于4-芳基取代基中的间位或对位取代而引起的5-质子的化学位移范围与取代苯侧链中相应质子的化学位移范围相似。

  DOI：

  10.1039/p19740000030

文献信息

• 신규한 셀레늄 고리 화합물 및 이의 제조방법
  申请人：KNU-Industry Cooperation Foundation 강원대학교산학협력단(220040088571) BRN ▼221-82-10213

  公开号：KR102037409B1

  公开（公告）日：2019-10-28

  2개 이상의 질소와 셀레늄이 고리 원소를 이루는 방향족 고리 화합물인 반응물질 1과, 적어도 이중 결합 이상의 결합을 갖는 반응물질 2를 로듐 촉매 반응 하에 반응시키는 단계; 및 상기 반응에 따라 상기 2개 이상의 질소위치에 상기 이중 결합 이상의 결합을 갖는 원소가 고리 원소로 첨가되어 셀레늄 고리 화합물이 합성되는 단계를 포함하며, 상기 반응물질 1 이고, 상기 반응물질 2는 알카인, 알켄, 나이트릴, 다이엔 결합 중 어느 하나를 포함하는 화합물인 것을 특징으로 하는 셀레늄 고리 화합물 합성 방법이 제공된다. (상기 R1, R2는 각각 수소, 할로겐기, 탄소수 1 내지 10의 알킬기, 탄소수 1 내지 10의 알케닐기, 탄소수 1 내지 10의 알키닐기, 탄소수 6 내지 12의 치환되거나 치환되지 않은 아릴기, 치환되거나 치환되지 않은 탄소수 5 내지 12의 헤테로아릴기 및 탄소수 1 내지 10의 알킬옥시로 이루어진 군으로부터 선택된 어느 하나이며, 상기 R1과 R2는 서로 연결되어 융합고리를 형성될 수 있음)

  2个以上的氮和硒形成环元素的芳香环化合物的反应物质1，至少具有双键以上的键合的反应物质2在铑催化反应下反应的步骤；以及根据所述反应，在所述2个以上的氮位置上，具有双键以上的键合的元素被添加为环元素以合成硒环化合物的步骤，其中所述反应物质1，并且所述反应物质2是包含碱金属，烯烃，腈，二烯键中的任何一种的化合物的硒环化合物合成方法，其特征在于提供。 （其中R1，R2分别为氢，卤素，1到10个碳原子的烷基，1到10个碳原子的烯基，1到10个碳原子的烷基，6到12个被取代或未被取代的芳基，5到12个被取代或未被取代的杂环芳基和1到10个烷氧基中的任何一个，其中R1和R2可以相互连接以形成融合环）
• The reaction of 1,2,3-thiadiazoles and 1,2,3-selenadiazoles with nonacarbonyldi-iron
  作者：T. L. Gilchrist、P. G. Mente、C. W. Rees

  DOI：10.1039/p19720002165

  日期：——

  Carbene complexes [µ-(thiophenacylidene)-bis(tricarbonyliron)(Fe–Fe) derivatives (9) and the seleno-analogues (10)] are obtained by the reaction of phenyl-substituted 1,2,3-thiadiazoles and 1,2,3-selenadiazoles with nonacarbonyldi-iron. When the substituents at positions 4 and 5 of the thiadiazoles and selenadiazoles are different, two isomeric carbene complexes are produced, the minor isomer in each

  通过苯基取代的1,2,3-噻二唑与1的反应，可得到碳原子络合物[µ-（噻吩亚苯基）-双（三羰基铁）（Fe - Fe）衍生物（9）和硒代类似物（10）]。 2,3-硒二唑与九碳二铁。当噻二唑和硒二唑的4和5位上的取代基不同时，会产生两种异构的卡宾配合物，每种情况下的次要异构体都是重排产物。有证据表明这种重排发生在卡宾配合物形成之前，并且可能涉及抗芳香族硫杂苯环和硒烯作为对称中间体。
• Synthesis and characterisation of cyclopentadienylcobalt and pentamethylcyclopentadienylcobalt diselenolenes
  作者：Christopher P. Morley、Richard R. Vaughan

  DOI：10.1039/dt9930000703

  日期：——

  Reaction of [Co(C5R15)(CO)2] (R1 = H or Me) with 1,2,3-selenadiazoles in toluene under reflux in the presence of an excess of elemental selenium leads in moderate yield to the diselenolenes [Co(C5R15)SeC(R2)=C(R3)Se}] [R2-R3=(CH2)6, CH=CH(CH2), or CH=CH(CH2)2CH=CH; R2=Ph, R3=H; R2=R3=Ph]. In particular this procedure provides access to novel compounds without electron-withdrawing substituents. The products have been characterised by H-1 NMR, IR, UV/VIS and mass spectroscopy, microanalysis and cyclic voltammetry. Each diselenolene undergoes a fully reversible one-electron reduction, and exhibits a low-energy electronic transition at ca. 800 nm. Of the substituents (R1,R2,R3), R1 has the greatest influence on the spectroscopic and electrochemical properties. For structurally similar compounds there is a linear correlation between the half-wave potential for the reduction and the energy of the first electronic absorption band.
• Synthesis and 1H nuclear magnetic resonance spectra of some aryl-1,2,3-selenadiazoles
  作者：Alon Caplin

  DOI：10.1039/p19740000030

  日期：——

  A series of aryl-1,2,3-selenadiazoles has been prepared, and their n.m.r. spectral parameters are recorded. The ranges of chemical shifts of the 5-proton due to meta- or para-substitution in the 4-aryl substituent are similar to those for the corresponding protons in the side-chains of substituted benzenes.

  制备了一系列芳基1,2,3-3-硒代二唑，并记录了它们的核磁共振光谱参数。由于4-芳基取代基中的间位或对位取代而引起的5-质子的化学位移范围与取代苯侧链中相应质子的化学位移范围相似。
• Transformations of selenadiazoliumyl-N-unsubstituted methanides (ylides) to new divinyl selenide derivatives and substituted 1,3,5-selenadiazines. Organoselenium systems from azolium 1,3-dipoles
  作者：Richard N. Butler、Anthony Fox

  DOI：10.1039/b007974j

  日期：——

  4,5-Diphenyl-1,2,3-selenadiazole and 3,5-diphenyl-1,2,4-selenadiazole were alkylated with trimethylsilylmethyl trifluoromethanesulfonate. Quaternisations occurred at N-3 and N-2 respectively. The salts were desilylated to generate transient selenadiazoliumylmethanide (ylide) intermediates. 4,5-Diphenyl-1,2,3-selenadiazol-3-ium-3-ylmethanide, 3, was trapped with dimethyl acetylenedicarboxylate and methyl propiolate in a cycloaddition–rearrangement reaction which gave the pyrazolylvinyl vinyl selenides 6 and 7. 3,5-Diphenyl-1,2,4-selenadiazol-2-ium-2-ylmethanide, 10, ring-expanded in situ to 4,6-diphenyl-2H-1,3,5-selenadiazine, 13.

  4,5-二苯基-1,2,3-硒二唑和 3,5-二苯基-1,2,4-硒二唑被三氟甲磺酸三甲基硅甲基酯烷基化。季化合物分别发生在 N-3 和 N-2。盐类经脱硅烷化后生成瞬时硒二唑甲酰亚胺（酰亚胺）中间体。4,5-二苯基-1,2,3-硒二唑-3-鎓-3-甲烷化物 3 与乙炔二甲酸二甲酯和丙炔酸甲酯发生环化重排反应，生成吡唑乙烯基硒化物 6 和 7。3,5-二苯基-1,2,4-硒二唑-2-鎓-2-基甲烷化物 10 在原位环展生成 4,6-二苯基-2H-1,3,5-硒二嗪 13。