difluoro(4-nitrophenyl)-λ³-iodane | 74953-38-1

• 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: difluoro(4-nitrophenyl)-λ³-iodane
• 英文别名: 4-nitroiodobenzene difluoride；1-difluoroiodanyl-4-nitro-benzene；1-Difluorjodanyl-4-nitro-benzol；Difluoro-(4-nitrophenyl)-lambda3-iodane；difluoro-(4-nitrophenyl)-λ3-iodane
• CAS: 74953-38-1
• 化学式: C₆H₄F₂INO₂
• 分子量: 287.005
• InChiKey: YQSSGMHPCRUUNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  difluoro(4-nitrophenyl)-λ³-iodane 以 氘代氯仿 、 二氯甲烷 为溶剂， 生成 (4-methoxyphenyl)(4-nitrophenyl)iodonium trifluoromethanesulfonate
  参考文献：
  名称：

  混合卤素/三氟甲磺酸 ArI(OTf)(X) 物种的合成、结构表征、反应性和催化活性

  摘要：

  混合的 λ 3 -碘代芳烃和具有 –OTf 配体的λ 3 -碘代芳烃都因其增强的反应性而备受追捧。在这里，我们描述了两种新的 ArI(OTf)(X) 物种的合成、反应性和综合表征，这是一类化合物，以前仅被用作反应性中间体，其中 X = Cl、F 及其与芳基底物的不同反应性。还描述了一种使用 Cl 2作为氯源和 ArI/HOTf 作为催化剂的用于失活芳烃亲电氯化的新催化系统。

  DOI：

  10.1039/d3dt00275f
• 作为产物：
  描述：

  4-nitrobenzene 在 氟化氢吡啶 作用下， 以 二氯甲烷 为溶剂， 以79 %的产率得到difluoro(4-nitrophenyl)-λ³-iodane
  参考文献：
  名称：

  Synthesis and Structural Verification of an ArI(OTf) ₂ , NO ₂ ‐Ph‐I(OTf) ₂ **

  摘要：

  AbstractPhI(OTf)2 and related ArI(OTf)2 species have been incorrectly invoked as intermediates in oxidation reactions for many years. We recently established that such compounds did not yet exist but remain an attractive target. Here we describe the synthesis, isolation, and structural characterization of NO2‐PhI(OTf)2, which is resistant to decomposition and more reactive than PhI(OTf)(OAc), the species previously misidentified as PhI(OTf)2.

  DOI：

  10.1002/anie.202212380
• 作为试剂：
  描述：

  2,2-bis(4-methylphenyl)-1,3-dithiane 在 difluoro(4-nitrophenyl)-λ³-iodane 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到1,1'-(Difluormethylen)bis(4-methylbenzol)
  参考文献：
  名称：

  Electrolytic Partial Fluorination of Organic Compounds. 14. The First Electrosynthesis of Hypervalent Iodobenzene Difluoride Derivatives and Its Application to Indirect Anodic gem-Difluorination

  摘要：

  The electrosynthesis of hypervalent iodobenzene difluorides was accomplished by anodic oxidation of p-nitro- and p-methoxyiodobenzenes with Et(3)N.3HF in anhydrous acetonitrile, and p-methoxyiodobenzene difluoride was used as a mediator for indirect anodic gem-difluorination of dithioketals.

  DOI：

  10.1021/jo00103a003

文献信息

• Deconstructing the Catalytic, <i>Vicinal</i> Difluorination of Alkenes: HF-Free Synthesis and Structural Study of <i>p</i>-TolIF₂
  作者：Jérôme C. Sarie、Christian Thiehoff、Richard J. Mudd、Constantin G. Daniliuc、Gerald Kehr、Ryan Gilmour

  DOI：10.1021/acs.joc.7b01671

  日期：2017.11.17

  an efficient synthesis of p-TolIF2 from p-TolI and Selectfluor is presented, together with a crystallographic and spectroscopic study. To mitigate safety concerns and simplify reaction execution, an HF-free protocol was devised employing CsF as a substitute fluoride source. The study provides insight into the initial I(I)→I(III) oxidation stage of the catalytic protocol using Selectfluor.

  最近，该实验室以及雅各布森及其同事独立报告了同时通过I（I）/ I（III）催化多联体实现烯烃邻二氟化的策略。两种策略都通过由ArI催化剂氧化产生的瞬时ArI（III）F 2物质进行。在此，提出了由p -TolI和Selectfluor有效合成p -TolIF 2的方法，并进行了晶体学和光谱学研究。为了减轻安全隐患并简化反应执行过程，设计了一种无氟协议，采用CsF作为氟化物的替代来源。该研究提供了使用Selectfluor进行催化方案的初始I（I）→I（III）氧化阶段的见解。
• Synthesen von aryljod(III)-difluoriden durch direktfluorierung von aryljodiden [1]
  作者：D. Naumann、G. Rüther

  DOI：10.1016/s0022-1139(00)82577-4

  日期：1980.3

  The aryl iodides C6H5I, o-XC6H4I (X = F, I), m-FC6H4I and p-XC6H4I (X = F, Cl, Br, I, CH3, NO2) react with elemental fluorine at about −100°C in CCl3F to form the corresponding aryl iodine difluorides without attack on the aromatic ring. Preparations, 19F-nmr, 1H-nmr as well as Raman spectra are described.

  芳基碘化物C 6 H 5 I，o-XC 6 H 4 I（X = F，I），m-FC 6 H 4 I和p-XC 6 H 4 I（X = F，Cl，Br，I， CH 3，NO 2）在CCl 3 F中约100°C下与元素氟反应，形成相应的芳基碘二氟化物，而不会侵蚀芳环。描述了19 F-nmr，1 H-nmr和拉曼光谱的制备方法。
• ArI(NTf₂)₂: the boundary of oxidative capacity for ArIL₂?
  作者：Lachlan Barwise、Jason D. Bennetts、Keith F. White、Jason L. Dutton

  DOI：10.1039/d3cc04563c

  日期：——

  NO₂–C₆H₄–I(NTf₂)₂ is synthesized and crystallographically characterized. Theoretical analysis suggests that ArI(NTf₂)₂ may be the limit of oxidative capacity for the ArIL₂ class of compounds.

  合成了 NO2-C6H4-I(NTf2)2，并对其进行了晶体学表征。理论分析表明，ArI(NTf2)2 可能是 ArIL2 类化合物氧化能力的极限。
• Sawaguchi, Masanori; Ayuba, Shinichi; Hara, Shoji, Synthesis, 2002, # 13, p. 1802 - 1803
  作者：Sawaguchi, Masanori、Ayuba, Shinichi、Hara, Shoji

  DOI：——

  日期：——
• Atopic dermatitis with mononuclear phagocytic activity deficiency
  作者：W.C.N. Forte、M.C. Santos de Menezes、S.M. Cipolli Guerra de Oliveira、S. Bruno

  DOI：10.1016/s0301-0546(02)79135-0

  日期：2002.1

  Five patients with atopic dermatitis, three males and two females, aged 2 to 17 years, had positive reactions to air allergens (Dermatophagoides pteronyssinus and/or farinae). All the patients suffered from severe recurrent dermatophytosis that responded poorly to antifungal treatment. The results of immunologic evaluation by laboratory tests were normal, except for a decrease in the ingestion phase by mononuclear phagocytes. After diagnosis of immunodeficiency, ketoconazole shampoo was used prophylactically and at the very first signs of recurrence of dermatophytosis, systemic antifungal treatment was started, without concurrent use of macrolides and with monitoring of hepatic function. The fungal infections responded well to this treatment and the patients' quality of life markedly improved.