2,2'-bis(isothiocyanato)biphenyl | 33904-05-1

• 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: 2,2'-bis(isothiocyanato)biphenyl
• 英文别名: 2,2'-bis(isothiocyamato)biphenyl；2,2′-diisothiocyanato-1,1′-biphenyl；2,2′-bis-(isothiocyanato)biphenyl；2,2'-bis(isothiocyanate)biphenyl；2,2'-Diisothiocyanatobiphenyl；1-Isothiocyanato-2-(2-isothiocyanatophenyl)benzene
• CAS: 33904-05-1
• 化学式: C₁₄H₈N₂S₂
• 分子量: 268.363
• InChiKey: ZRAUTPFJSLRDDA-UHFFFAOYSA-N

物化性质

• 熔点：
  32-34 °C
• 沸点：
  468.4±38.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  88.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2'-bis(isothiocyanato)biphenyl 在 magnesium sulfate 、 mercury(II) oxide 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 106.0h， 生成 bis<1,3>diazepino>-1,3-diazetidine
  参考文献：
  名称：

  Preparation and Intramolecular Cyclization of Bis(carbodiimides). Synthesis and X-ray Structure of 1,3-Diazetidine-2,4-diimine Derivatives

  摘要：

  Aza-Wittig reactions of bis(iminophosphorane) 1 derived from 2,2'-diazidobiphenyl with aromatic isocyanates provided dibenzo[d,f]-1,3-diazetidino[1,2-a]diazepine derivatives 2 in moderate yields. Similar results can be achieved from the reaction of 2,2'-bis(isothiocyanato)biphenyl 4 with aryliminophosphoranes. Treatment of bis(isothiocyanate) 4 with arylamines and further dehydrosulfurization of the resulting bis(thioureas) leads to the seven-membered ring guanidines 8. N-2-(2'-Azido)biphenyI-N'-arylcarbodiimides 13 react with 1 equiv of triphenylphosphane to give zwitterionic compounds 15, which undergo either hydrolytic cleavage to afford the guanidines 8 or react with 1 equiv of aromatic isocyanates to provide 2. Cross-experiments suggest that the: conversion 15 --> 2 takes place through a nonisolable bis(carbodiimide) that undergoes an intramolecular [2 + 2] cycloaddition at the final step. The reaction of bis(iminophosphorane) 1 with an excess of carbon dioxide leads to a mixture of the tricyclic 1,3-diazetidine derivative 6 and the 14-membered cyclic bis(carbodiimide) 23, which decomposes by thermal treatment. Compound 6 can also be obtained along with the seven-membered cyclic urea derivatives 24 from the reaction of bis(iminophosphorane) 1 with the carbon dioxide source Boc(2)O/DMAP system. A comprehensive mechanistic scheme for the aza-Wittig reactions studied is conveniently presented. The molecular and crystal structures of 1-(4-methoxyphenyl)-2-(4-methoxyphenyl)iminodibenzo[d,f]-1,3-diazetidino-[1,2-a]diazepine (2c) and [a,c]bis[dibenzo[d,f][1,3]diazepino]-1,3]diazepino]-1,3-diazetidine (6) have been determined by X-ray analysis.

  DOI：

  10.1021/jo981339v
• 作为产物：
  描述：

  2,2'-二硝基联苯 在 palladium on activated charcoal 、 氢气 、 potassium carbonate 作用下， 以 氯仿 、 乙酸乙酯 为溶剂， 反应 6.5h， 生成 2,2'-bis(isothiocyanato)biphenyl
  参考文献：
  名称：

  68Ga-NOTA-Biphenyl-c（RGDyK）的合成及对整合素αvβ3定量的初步评估

  摘要：

  精氨酸-甘氨酸-天冬氨酸（RGD）肽结合整联α v β 3，其在肿瘤血管生成和转移了至关重要的作用。先前开发的68 Ga标记的环状RGD肽可从循环系统中迅速排出。在本研究中，我们开发了68 Ga-标记的环状RGD肽与螯合剂和RGD肽，间联苯基，即，68 Ga的NOTA联苯-C（RGDyK ）。然后，我们进行与参考化合物的比较，即，68 Ga的NOTA-C（RGDyK）。68 Ga‐NOTA‐Biphenyl‐c（RGDyK ）比亲水性少37％68 Ga‐NOTA‐c（RGDyK）。用于正电子发射断层成像，68 Ga的NOTA联苯-C（RGDyK）具有更长的保留时间，并显示在肿瘤中比更高的信噪比68 Ga的NOTA-C（RGDyK）。但是，联苯-放射肽显示出较高的非特异性结合。从这些角度来看，将联苯基引入RGD会产生利弊。

  DOI：

  10.1002/bkcs.11316

文献信息

• TfOH-Promoted Transition-Metal-Free Cascade Trifluoroethylation/Cyclization of Organic Isothiocyanates by Phenyl(2,2,2-trifluoroethyl)iodonium Triflate
  作者：Cheng-Long Zhao、Qiu-Yan Han、Cheng-Pan Zhang

  DOI：10.1021/acs.orglett.8b02793

  日期：2018.10.19

  An efficient and transition-metal-free method for the synthesis of the structurally diversified trifluoroethylthiol phenanthridines and 3,4-dihydroisoquinolines is described. Various 2-isothiocyanobiaryls and aryl alkyl isothiocyanates reacted with phenyl(2,2,2-trifluoroethyl)iodonium triflate in CH2Cl2 in the presence of trifluoromethanesulfonic acid at 40 °C to form the corresponding trifluoroet

  描述了一种有效且无过渡金属的方法，用于合成结构上多样化的三氟乙基硫醇菲和3,4-二氢异喹啉。在三氟甲磺酸存在下，在40°C下，在CH 2 Cl 2中，各种2-异硫氰基联芳基和异硫氰酸芳基烷基酯与三氟苯基苯基（2,2,2-三氟乙基）碘鎓反应，形成相应的三氟乙基化/环化产物，其定量收率良好。 。这项工作代表了在不存在过渡金属催化剂的情况下，通过一锅法从异硫氰酸酯构建三氟乙基硫醇菲啶和异喹啉衍生物的第一个方法。
• 바이페닐 함유 RGD 유도체, 그 제조방법 및 그것을 포함하는 방사성의약품
  申请人：KOREA INSTITUTE OF RADIOLOGICAL & MEDICAL SCIENCES 한국원자력의학원(220070148654) BRN ▼217-82-04745

  公开号：KR101918205B1

  公开（公告）日：2018-11-13

  본 발명의 일 양상은 종양 선택성 RGD 펩티드 및 방사성동위원소 표지용 리간드가 2,2'-디아미노바이페닐의 양쪽의 아민에 각각 공유결합된 구조를 갖는 화학식 I의 화합물, 그 화합물에 방사성동위원소가 결합된 방사성의약품용 화합물, 그 방사성의약품용 화합물의 제조방법, 및 그 방사성의약품용 화합물을 포함하는 방사성의약품을 제공한다.

  本发明的一种形式涉及化学式I的化合物，该化合物具有在2,2'-二氨基联苯的两个氨基上各自共价结合的肿瘤选择性RGD肽和放射性同位素标记配体的结构，以及与放射性同位素结合的放射性药物用化合物，该放射性药物用化合物的制备方法和包含该放射性药物用化合物的放射性药物。
• Exploring the Conversion of Macrocyclic 2,2′-Biaryl Bis(thioureas) into Cyclic Monothioureas: An Experimental and Computational Investigation
  作者：Mateo Alajarin、Carmen Lopez-Leonardo、Raul-Angel Orenes、Aurelia Pastor、Pilar Sanchez-Andrada、Angel Vidal

  DOI：10.1021/acs.joc.8b02496

  日期：2018.11.16

  Macrocyclic bis(thioureas) derived from 2,2′-biphenyl and binaphthyl skeletons have been synthesized by reaction of 2,2′-diaminobiaryl and 2,2′-bis(isothiocyanato)biaryl derivatives. The splitting of these bis(thioureas) into two units of the respective cyclic monothioureas has been monitored by NMR, shedding some light on the factors that control these processes. Additionally, a computational study

  通过2,2'-二氨基联芳基和2,2'-双（异硫氰酸根合）联芳基衍生物的反应合成了衍生自2,2'-联苯和联萘骨架的大环双（硫脲）。已通过NMR监测了这些双（硫脲）分裂成两个环状单硫脲的单元，从而为控制这些过程的因素提供了一些线索。此外，一项计算研究还揭示了将3，2'-联苯衍生的双（硫脲）转化为相应的单硫脲的多达三种机理。所提出的机制将水分子的参与作为一种有效的质子转换以及不同类别的假定中间体。计算研究还支持了硫脲基团参与过多过程（如质子平衡，顺式⇆反式异构化。
• [EN] TINTED ARTICLE HAVING A HIGH REFRACTIVE INDEX<br/>[FR] ARTICLE TEINTÉ AYANT UN INDICE DE RÉFRACTION ÉLEVÉ
  申请人：PPG IND OHIO INC

  公开号：WO2009038937A1

  公开（公告）日：2009-03-26

  Disclosed is a tinted article formed from a substrate having a refractive index of at least 1.57 comprising at least partially polymerized sulfur-containing polyurethane material and/or at least partially polymerized sulfur-containing polyurethaneurea material; an intermediate coating applied to at least a portion of the substrate; a tintable hardcoat applied to at least a portion of the intermediate coating; and tint applied to at least a portion of the tintable hardcoat. Methods for preparing the tinted articles also are provided.
• Preparation and Intramolecular Cyclization of Bis(carbodiimides). Synthesis and X-ray Structure of 1,3-Diazetidine-2,4-diimine Derivatives
  作者：Mateo Alajarín、Pedro Molina、Pilar Sánchez-Andrada、M. Concepción Foces-Foces

  DOI：10.1021/jo981339v

  日期：1999.2.1

  Aza-Wittig reactions of bis(iminophosphorane) 1 derived from 2,2'-diazidobiphenyl with aromatic isocyanates provided dibenzo[d,f]-1,3-diazetidino[1,2-a]diazepine derivatives 2 in moderate yields. Similar results can be achieved from the reaction of 2,2'-bis(isothiocyanato)biphenyl 4 with aryliminophosphoranes. Treatment of bis(isothiocyanate) 4 with arylamines and further dehydrosulfurization of the resulting bis(thioureas) leads to the seven-membered ring guanidines 8. N-2-(2'-Azido)biphenyI-N'-arylcarbodiimides 13 react with 1 equiv of triphenylphosphane to give zwitterionic compounds 15, which undergo either hydrolytic cleavage to afford the guanidines 8 or react with 1 equiv of aromatic isocyanates to provide 2. Cross-experiments suggest that the: conversion 15 --> 2 takes place through a nonisolable bis(carbodiimide) that undergoes an intramolecular [2 + 2] cycloaddition at the final step. The reaction of bis(iminophosphorane) 1 with an excess of carbon dioxide leads to a mixture of the tricyclic 1,3-diazetidine derivative 6 and the 14-membered cyclic bis(carbodiimide) 23, which decomposes by thermal treatment. Compound 6 can also be obtained along with the seven-membered cyclic urea derivatives 24 from the reaction of bis(iminophosphorane) 1 with the carbon dioxide source Boc(2)O/DMAP system. A comprehensive mechanistic scheme for the aza-Wittig reactions studied is conveniently presented. The molecular and crystal structures of 1-(4-methoxyphenyl)-2-(4-methoxyphenyl)iminodibenzo[d,f]-1,3-diazetidino-[1,2-a]diazepine (2c) and [a,c]bis[dibenzo[d,f][1,3]diazepino]-1,3]diazepino]-1,3-diazetidine (6) have been determined by X-ray analysis.