Dibrom-deuterio-methan | 2253-83-0

• 物质功能分类: 化学试剂 - 氘代试剂
• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: Dibrom-deuterio-methan
• 英文别名: Methane-d, dibromo-；dibromo(deuterio)methane
• CAS: 2253-83-0
• 化学式: CH₂Br₂
• 分子量: 174.827
• InChiKey: FJBFPHVGVWTDIP-MICDWDOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  3
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  Dibrom-deuterio-methan 在 [¹⁸F]fluoride ion-potassium⁺-4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane complex 作用下， 以 乙腈 为溶剂， 反应 0.25h， 生成 [¹⁸F]fluoromethyl bromide-d₂
  参考文献：
  名称：

  3-Substituted 1,5-Diaryl-1H-1,2,4-triazoles as Prospective PET Radioligands for Imaging Brain COX-1 in Monkey. Part 1: Synthesis and Pharmacology

  摘要：

  Cyclooxygenase-1 (COX-1) is a key enzyme in the biosynthesis of proinflammatory thromboxanes and prostaglandins and is found in glial and neuronal cells within brain. COX-1 expression is implicated in numerous neuroinflammatory states. We aim to find a direct-acting positron emission tomography (PET) radioligand for imaging COX-1 in human brain as a potential biomarker of neuroinflammation and for serving as a tool in drug development. Seventeen 3-substituted 1,5-diaryl-1H-1,2,4-triazoles were prepared as prospective COX-1 PET radioligands. From this set, three 1,5-(4-methoxypheny1)-1H-1,2,4-triazoles, carrying a 3-methoxy (5), 3-(1,1,1-trifluoroethoxy) (20), or 3-fluoromethoxy substituent (6), were selected for radioligand development, based mainly on their high affinities and selectivities for inhibiting human COX-1, absence of carboxyl group, moderate computed lipophilicities, and scope for radiolabeling with carbon-11 (t(1/2) = 20.4 min) or fluorine-18 (t(1/2) = 109.8 min). Methods were developed for producing [C-11]5, [C-11]20, and [d(2)-F-18]6 from hydroxy precursors in a form ready for intravenous injection for prospective evaluation in monkey with PET.

  DOI：

  10.1021/acschemneuro.8b00102
• 作为产物：
  描述：

  三溴甲烷 在 trisodium arsenite 、 乙醇-D1 、 重水 作用下， 反应 4.5h， 生成 Dibrom-deuterio-methan
  参考文献：
  名称：

  Novel pharmaceutical compounds

  摘要：

  本发明涉及替代他达拉非的衍生物，在苯并二氧杂环戊二烷环的氧原子之间的亚甲基碳原子上取代氟，并且可选地进一步用氘原子取代正常丰富的氢，以及用13C取代正常丰富的12C。这些化合物是选择性的PDE5抑制剂，并具有有利的生物制药和药代动力学性质。该发明还提供了包含这些化合物的组合物和治疗对PDE5抑制有响应的疾病和症状的方法，单独或与其他药物联合使用。

  公开号：

  US20070037815A1

文献信息

• Highly Enantioselective Synthesis of 1,2,3-Substituted Cyclopropanes by Using α-Iodo- and α-Chloromethylzinc Carbenoids
  作者：Louis-Philippe B. Beaulieu、Lucie E. Zimmer、Alexandre Gagnon、André B. Charette

  DOI：10.1002/chem.201202528

  日期：2012.11.12

  α‐chlorozinc carbenoids by using a dioxaborolane‐derived chiral ligand. The synthetically useful iodocyclopropane building blocks were derivatized by an electrophilic trapping of the corresponding cyclopropyl lithium species or a Negishi coupling to give access to a variety of enantioenriched 1,2,3‐substituted cyclopropanes. The synthetic utility of this method was demonstrated by the formal synthesis of an

  此，我们报告的对映和非对映选择性形成反式-碘和反式通过使用二氧硼戊环衍生的手性配体从-chlorocyclopropanesα碘-和α-chlorozinc卡宾。可以通过亲电捕集相应的环丙基锂物质或使用Negishi偶联剂衍生出可用于合成的碘代环丙烷结构单元，从而获得各种对映体富集的1,2,3-取代的环丙烷。HIV-1蛋白酶抑制剂的正式合成证明了该方法的合成效用。另外，还研究了相关的立体选择性溴环丙烷化。还介绍了有关卤代碘甲基锌类胡萝卜素相对亲电性的新见解。
• Probing Hyperconjugation Experimentally with the Conformational Deuterium Isotope Effect
  作者：Kyle T. Greenway、Anthony G. Bischoff、B. Mario Pinto

  DOI：10.1021/jo3017988

  日期：2012.10.19

  deal of interest in the anomeric effect, anomeric-like hyperconjugative effects have been thoroughly investigated in oxygen-containing systems. However, such interactions in the second- and third-row chalcogens are less well-understood and have generated some controversy. Here, we show that the conformational deuterium isotope effect, in combination with Saunders’ isotopic perturbation method, permits

  超共轭作用是许多具有根本和实际重要性的化学现象的基础。由于对端基异构作用的极大兴趣，已经在含氧体系中彻底研究了类似端基的超共轭作用。但是，在第二行和第三行硫族元素中的这种相互作用了解得较少，并引起了一些争议。在这里，我们表明，构象氘同位素效应与桑德斯的同位素摄动方法相结合，可通过可变温度，动态NMR光谱法对二恶烷，二噻吩和二硒烷类似物中的构象平衡进行敏感而直接的实验探测。我们发现，氧，硫和硒类似物的构象氘同位素效应强度分别为252.1、28.3和7.1 J / mol（±10％）。在红外光谱的支持下，并与DFT计算和自然键序分析相一致，在整个过程中x →σC –H（D）相互作用。
• External Flash Generation of Carbenoids Enables Monodeuteration of Dihalomethanes
  作者：Kazuhiro Okamoto、Ryosuke Higuma、Kensuke Muta、Keita Fukumoto、Yuta Tsuchihashi、Yosuke Ashikari、Aiichiro Nagaki

  DOI：10.1002/chem.202301738

  日期：2023.8.21

  In this study, incorporation of one deuterium atom was achieved by H−D exchange of one of the two identical methylene protons in various dihalomethanes (halogen=Cl, Br, and I) through a rapid‐mixing microflow reaction of lithium diisopropylamide as a strong base and deuterated methanol as a deuteration reagent. Generation of highly unstable carbenoid intermediate and suppression of its decomposition were successfully controlled under high flow‐rate conditions. Monofunctionalization of diiodomethane afforded various building blocks composed of boryl, stannyl, and silyl groups. The monodeuterated diiodomethane, which served as a deuterated C1 source, was subsequently subjected to diverted functionalization methods to afford various products including biologically important molecules bearing isotope labelling at specific positions and homologation products with monodeuteration.

  摘要 在这项研究中，通过以二异丙基酰胺锂为强碱、以氘化甲醇为氘化试剂的快速混合微流反应，在各种二卤甲烷（卤素=Cl、Br 和 I）的两个相同亚甲基质子中的一个进行 H-D 交换，实现了一个氘原子的掺入。在高流速条件下，成功控制了高度不稳定的类羰基中间体的生成并抑制了其分解。二碘甲烷的单官能化产生了由硼烷基、锡烷基和硅烷基组成的各种结构单元。作为氘化 C1 源的单氘化二碘甲烷随后通过转移官能化方法得到了各种产物，包括在特定位置带有同位素标记的重要生物分子和单氘化同源产物。
• Eaborn, Colin; Stanczyk, Wlodzimierz A., Journal of the Chemical Society. Perkin transactions II, 1991, # 4, p. 471 - 473
  作者：Eaborn, Colin、Stanczyk, Wlodzimierz A.

  DOI：——

  日期：——
• WO2007/16431
  申请人：——

  公开号：——

  公开（公告）日：——