1-(difluormethyl)-4-(dimethylamino)benzol | 705-39-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-(difluormethyl)-4-(dimethylamino)benzol
• 英文别名: 4-(difluoromethyl)-N,N-dimethylaniline；N,N-dimethyl-4-(difluoromethyl)aniline；p-Dimethylaminobenzyliden-fluorid
• CAS: 705-39-5
• 化学式: C₉H₁₁F₂N
• 分子量: 171.19
• InChiKey: RHWZABSJSJYUPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对二甲氨基苯甲醛 在 sulfur tetrafluoride 、 水 作用下， 以40%的产率得到1-(difluormethyl)-4-(dimethylamino)benzol
  参考文献：
  名称：

  Haas, Alois; Spitzer, Martin; Lieb, Max, Chemische Berichte, 1988, vol. 121, p. 1329 - 1340

  摘要：

  DOI：

文献信息

• METHOD AND REAGENT FOR DEOXYFLUORINATION
  申请人：South Dakota Board of Regents

  公开号：US20210155561A1

  公开（公告）日：2021-05-27

  A safe, simple, and selective method and reagent for deoxyfluorination is disclosed. With the method and reagent disclosed herein, organic compounds such as carboxylic acids, carboxylates, carboxylic acid anhydrides, aldehydes, and alcohols can be fluorinated by using the most common nucleophilic fluorinating reagents and electron deficient fluoroarenes as mediators under mild conditions, giving corresponding fluoroorganic compounds in excellent yield with a wide range of functional group compatibility and easy product purification. For example, directly utilizing KF for deoxyfluorination of carboxylic acids provides the most economical and the safest pathway to access acyl fluorides, key intermediates for syntheses of peptide, amide, ester, and dry fluoride salts.

  揭示了一种安全、简单和选择性的脱氧氟化方法和试剂。利用本公开的方法和试剂，有机化合物如羧酸、羧酸盐、羧酸酐、醛和醇可以在温和条件下通过使用最常见的亲核氟化试剂和电子亏损的氟代芳烃作为介质进行氟化，产率极高地得到相应的氟有机化合物，具有广泛的官能团兼容性和易于产品纯化。例如，直接利用KF对羧酸进行脱氧氟化提供了最经济和最安全的途径，以获得酰氟，这是合成肽、酰胺、酯和干氟化盐的关键中间体。
• Sandmeyer Difluoromethylation of (Hetero-)Arenediazonium Salts
  作者：Christian Matheis、Kévin Jouvin、Lukas J. Goossen

  DOI：10.1021/ol5030037

  日期：2014.11.21

  straightforward conversion of (hetero-)arenediazonium salts into the corresponding difluoromethyl (hetero-)arenes under mild conditions. The actual difluoromethylating reagent, a difluoromethyl–copper complex, is formed in situ from copper thiocyanate and TMS–CF2H. The diazonium salts are either preformed or generated in situ from broadly available aromatic amines.

  已经开发了Sandmeyer型二氟甲基化方法，其允许在温和的条件下将（杂）芳烯二鎓盐直接转化为相应的二氟甲基（杂）芳烃。实际的二氟甲基化试剂，即二氟甲基-铜络合物，是由硫氰酸铜和TMS-CF 2 H原位形成的。重氮盐既可以预先形成，也可以由广泛使用的芳族胺原位生成。
• [Ph ₄ P] ⁺ [Cu(CF ₂ H) ₂ ] ⁻ : A Powerful Difluoromethylating Reagent Inspired by Mechanistic Investigation
  作者：Haiwei Zhao、Xuebing B. Leng、Wei Zhang、Qilong Shen

  DOI：10.1002/anie.202210151

  日期：2022.10.17

  A powerful difluoromethylating reagent [Ph4P]+[Cu(CF2H)2]− that was able to difluoromethylate a variety of aryl and alkyl electrophiles was developed. In the presence of an oxidant, complex 2 also reacted with various lithium nbutyl arylboronic acid pinacol esters, alkyne and heteroarene. Moreover, complex 2 could transmetalate the difluoromethyl reagent to other metals such as [Ph4P]+[Cu(Cl2)]− and

  开发了一种强大的二氟甲基化试剂 [Ph 4 P] + [Cu(CF 2 H) 2 ] −，它能够二氟甲基化各种芳基和烷基亲电子试剂。在氧化剂存在下，络合物2还与各种锂正丁基芳基硼酸频哪醇酯、炔烃和杂芳烃反应。此外，络合物2可以将二氟甲基试剂金属转移到其他金属，例如 [Ph 4 P] + [Cu(Cl 2 )] -和 [(DPPF)Pd(Cl) 2 ]。
• Electronically Ambivalent Hydrodefluorination of Aryl‐CF ₃ groups enabled by Electrochemical Deep‐Reduction on a Ni Cathode
  作者：John R. Box、Mickaël E. Avanthay、Darren L. Poole、Alastair J. J. Lennox

  DOI：10.1002/anie.202218195

  日期：2023.3.13

  We report a general procedure for the direct mono- and di-hydrodefluorination of ArCF3 compounds. Exploiting the tunability of electrochemistry and the selectivity enabled by a Ni cathode, the deep reduction garners high selectivity with good to excellent yields up to gram scale. The late-stage peripheral editing of CF3 feedstocks to construct fluoromethyl moieties will aid the rapid diversification

  我们报告了ArCF 3化合物直接单加氢和双加氢脱氟的一般程序。利用电化学的可调性和镍阴极实现的选择性，深度还原获得了高选择性，并且产量高达克级。用于构建氟甲基部分的 CF 3原料的后期外围编辑将有助于先导化合物和化合物库的快速多样化。
• Pasternak,V.I. et al., Journal of Organic Chemistry USSR (English Translation), 1978, vol. 14, p. 2298 - 2301
  作者：Pasternak,V.I. et al.

  DOI：——

  日期：——

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