联苯-D2 | 6120-99-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 联苯-D2
• 英文名称: 4,4'-dideuterio-biphenyl
• 英文别名: 1,1'-biphenyl-4,4'-d₂；Diphenyl-4,4'-D2；1-deuterio-4-(4-deuteriophenyl)benzene
• CAS: 6120-99-6
• 化学式: C₁₂H₁₀
• 分子量: 156.196
• InChiKey: ZUOUZKKEUPVFJK-QDNHWIQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  联苯-D2 在 氨 、 lithium 作用下， 反应 0.5h， 生成 6,4'-[²H₂]-3-phenyl-1,4-cyclohexadiene
  参考文献：
  名称：

  Stepwise Preparation of All-cis 1,3,4-Trifluoro-2-phenylcyclohexane, Avoiding a Phenonium Intermediate

  摘要：

  The original synthesis of all-cis 1,2,4,S,-tetrafluoro-2-phenylcyclohexane resulted in a trifluorocydohexene as a significant co-product of the final fluorination step. This product was notable in that an elimination reaction was accompanied by C-F bond formation that had occurred with a retention of configuration. In order to deconvolute this reaction, the two isomers of the ditriflate diol precursor were separated, and they were each treated independently with Et3N center dot 3HF. One gave the original all-cis 1,2,4,5,tetrafluoro-2-phenylcyclohexane and the other the trifluorocydohexene. A deuterium labeling experiment was carried out, resulting in a distribution of the isotope in the trifluorocyclohexene consistent with an intermediate (symmetrical) phenonium intermediate. Cognisant of this, a controlled elimination reaction of one of the diastereoisomers with DBU, followed by hydrogenation, gave a cydohexane triflate, which, on fluorination, gave the all-cis 1,2,3-trifluoro-2-phenylcyclohexane now with an inversion of configuration.

  DOI：

  10.1021/jo501432x
• 作为产物：
  描述：

  氯苯-4-D1 生成 联苯-D2
  参考文献：
  名称：

  Memory Effects in Pd-Catalysed Allylic Alkylation: Stereochemical Labelling through Isotopic Desymmetrization

  摘要：

  H-2-Labelled and O-18-labelled cyclopentenyl esters (+/-)-4 and (+/-)-5 are used as probes for memory effects in Pd-catalysed allylic alkylation. H-2-Labelled alkylation product 6 arising from stereospecific Pd-catalysed reaction of (+/-)-4 was analysed by a novel C-13 NMR method involving H-2-isotope shifts and paramagnetic diastereotopic shifts. When catalysts bearing the Trost modular ligand (R,R)-3 were employed, variable memory effects were observed with the slower reacting chirality mismatched (R)-4 substrate-catalyst pairing. The memory effect is dependent on nucleofuge steric bulk and not pK(a). Attack by [LiCH(CO2CH3)(2)] occurs with reversed site selectivity but (R)-4 remains the mismatched substrate. Mismatched ionisation leading to a Pd-pi-allyl in which (R,R)-3 acts as a monophosphine ligand may explain the memory effect.

  DOI：

  10.1002/(sici)1521-3765(19981204)4:12<2539::aid-chem2539>3.0.co;2-1

文献信息

• 一种由芳香族C-N/O/Cl/Br/I键还原为芳香族C-H/D的方法
  申请人：遵义医科大学

  公开号：CN113354498B

  公开（公告）日：2023-08-18

  一种由芳香族C‑N/O/Cl/Br/I键还原为芳香族C‑H/D的方法，该方法以稳定的芳香季铵盐、芳香三氟磺酸酯、芳香卤代物为原料，在加入碱及溶剂后，由可见光或紫外光照射即可高效率地制备芳香族化合物或氘代芳香族化合物。该方法对于生物医药化工中间体的合成提供一种无需使用催化剂或过渡金属化合物，无需额外添加还原剂，仅仅以廉价的碱为添加剂，在廉价易得的溶剂或氘代溶剂中由可见光或紫外光诱导，即可高效地将稳定的芳香族C‑N/O/Cl/Br/I化学键转化为芳香族C‑H/D键。整个生产过程绿色环保、成本低廉、底物适用性广、产率高、氘代率高、操作简便、无爆炸风险，和以往的生产工艺相比，具有十分显著的优势。
• Photoinduced catalyst-free deborylation–deuteration of arylboronic acids with D₂O
  作者：Yatao Lang、Xiangjun Peng、Chao-Jun Li、Huiying Zeng

  DOI：10.1039/d0gc01649g

  日期：——

  deborylation–deuteration of arylboronic acids with D2O is reported. The protocol was compatible with a variety of functionalities, including halogen, alkoxy, cyano, sulfonyl, trimethylsilyl, trifluoromethoxy, alkyl, hydroxyl, free acid, amide, and heteroaromatic rings. A wide range of deuterated products were obtained in good yields with a high level of deuteration. This method provides a green and practical

  在本文中，报道了用D 2 O进行的新型光诱导的无催化剂脱芳基化-芳基硼酸氘化反应。该方案与多种功能兼容，包括卤素，烷氧基，氰基，磺酰基，三甲基甲硅烷基，三氟甲氧基，烷基，羟基，游离酸，酰胺和杂芳族环。以高收率和高收率获得了多种氘代产品。该方法为在温和条件下合成氘标记的化合物提供了绿色实用的途径。
• Palladium‐Catalyzed Deuteration of Arylketone Oxime Ethers
  作者：Zhen‐Yu Wang、Xu Zhang、Wen‐Qing Chen、Guo‐Dong Sun、Xing Wang、Lin Tan、Hui Xu、Hui‐Xiong Dai

  DOI：10.1002/anie.202319773

  日期：2024.3.18

  A palladium-catalyzed deuteration of arylketone oxime ethers has been realized. Regioselective deuteration of some biologically important drugs and natural products is showcased via Friedel–Crafts acylation and subsequent deacylative deuteration. Vicinal difunctionalization of electro-rich arenes is achieved by using the ketone as both directing group and leaving group.

  已经实现了芳酮肟醚的钯催化氘化。通过弗里德尔-克拉夫茨酰化和随后的脱酰氘化展示了一些具有重要生物学意义的药物和天然产物的区域选择性氘化。富电芳烃的邻位双官能化是通过使用酮作为导向基团和离去基团来实现的。
• Relationships Between Defectivity and Porosity in High Surface Area Porous Aromatic Frameworks**
  作者：Anthony J. Porath、Tony Lybrand、James R. Bour

  DOI：10.1002/anie.202314120

  日期：2024.1.15

  Porous aromatic framework (PAF) microporosity is known to be strongly dependent on synthetic approach but little is known about why certain reactions yield significantly and consistently more porous PAFs. This article explores the connections between synthetic pathway, PAF defectivity, and microporosity. Using a network disassembly strategy, we show that defectivity is highly dependent on synthetic approach and that more defective PAFs are associated with lower surface areas and pore volumes. This empirical association is corroborated through systematic introduction of defects to a modelPAF, which results in significant reduction of apparent surface area and pore volumes. Taken together, these data suggest that only highly efficient coupling reactions should be targeted for the synthesis of ultra‐high surface area porous aromatic frameworks.

  摘要 众所周知，多孔芳香族框架（PAF）的微孔率与合成方法密切相关，但人们对某些反应为什么会产生明显且持续的多孔 PAF 却知之甚少。本文探讨了合成途径、PAF 缺陷和微孔之间的联系。利用网络分解策略，我们发现缺陷率与合成途径有很大关系，缺陷率越高的 PAF 表面积和孔体积越小。通过在模型 PAF 中系统地引入缺陷，显著减少了表观表面积和孔体积，从而证实了这一经验关联。总之，这些数据表明，只有高效的偶联反应才是合成超高比表面积多孔芳香族框架的目标。
• Convenient Deuteration of Bromo Aromatic Compounds by Reductive Debromination with Sodium Amalgam in CH₃OD
  作者：Yozo Miura、Hiroyuki Oka、Eiji Yamano、Masanori Morita

  DOI：10.1021/jo9619037

  日期：1997.2.1