N,N-dibenzyl-2,2,2-trichloroacetamide

• 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: N,N-dibenzyl-2,2,2-trichloroacetamide
• 化学式: C₁₆H₁₄Cl₃NO
• 分子量: 342.652
• InChiKey: NVGXIQANLRYTRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-dibenzyl-2,2,2-trichloroacetamide 在 正丁基锂 、 [Rh2(O2CCPh3)4] 、 三丁基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 6.17h， 生成 N¹,N¹-dibenzyl,N²-(4-nitrobenzenesulfonyl)-(Z)-pentadienamidine
  参考文献：
  名称：

  通过调节铑 (II) 催化的 1,2-H 转变中的 N-磺酰基来控制 Z-α,β-不饱和脒的合成选择性

  摘要：

  α-重氮脒脱氮后，羧酸铑（II）催化1,2-H转变，可以高产率合成α,β-不饱和脒。通过抑制涉及分子内氧转移的副反应，使用大的羧酸铑 (II) 配体和缺电子的N-磺酰基可实现独特的Z-选择性和优异的产率。

  DOI：

  10.1002/ejoc.202101235
• 作为产物：
  描述：

  苄胺 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 N,N-dibenzyl-2,2,2-trichloroacetamide
  参考文献：
  名称：

  Dearomative radical spirocyclization from N-ce:raghubenzyltrichloroacetamides revisited using a copper(I)-mediated atom transfer reaction leading to 2-azaspiro[4.5]decanes

  摘要：

  An atom transfer radical dearomatizing spirocyclization from N-benzyltrichloroacetamides using CuCl regioselectively leads to 2-azaspiro[4.5]decadienes, in which the labile allylic chlorine atom is easily replaced by a hydroxyl group in aqueous medium or by quenching with methanol or allylamine. After oxidation of the target compound, the N-tert-butyl group can be removed from the resulting spirocyclohexanedienone. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.019

文献信息

• Spirolactams by a novel ipso-radical cyclisation and loss of aromaticity
  作者：Jean Boivin、Mohammed Yousfi、Samir Z. Zard

  DOI：10.1016/s0040-4039(97)01362-2

  日期：1997.8

  Spirolactams are obtained by ipso radical cyclisation when various substituted N-benzyl trichloroacetamides are subjected to the nickel powder/acetic acid reducing system.

  Spirolactams通过获得本位自由基环化时的各种取代的N-苄基trichloroacetamides经受镍粉末/乙酸还原系统。
• Cytotoxic Assessment of 3,3-Dichloro-β-Lactams Prepared through Microwave-Assisted Benzylic C-H Activation from Benzyl-Tethered Trichloroacetamides Catalyzed by RuCl2(PPh3)3
  作者：Faïza Diaba、Alexandra G. Sandor、María del Carmen Morán

  DOI：10.3390/molecules27185975

  日期：——

  Natural and synthetic β-lactam derivatives constitute an interesting class of compounds due to their diverse biological activity. Mostly used as antibiotics, they were also found to have antitubercular, anticancer and antidiabetic activities, among others. In this investigation, six new 3,3-dichloro-β-lactams prepared in a previous work were evaluated for their hemolytic and cytotoxic properties. The results showed that the proposed compounds have non-hemolytic properties and exhibited an interesting cytotoxic activity toward squamous cell carcinoma (A431 cell line), which was highly dependent on the structure and concentration of these β-lactams. Among the molecules tested, 2b was the most cytotoxic, with the lowest IC50 values (30–47 µg/mL) and a promising selectivity against the tumor cells compared with non-tumoral cells.

  天然和合成的 β-内酰胺衍生物具有多种生物活性，是一类有趣的化合物。它们大多被用作抗生素，还被发现具有抗结核、抗癌和抗糖尿病等活性。在这项研究中，我们对之前工作中制备的六种新的 3,3-二氯-β-内酰胺进行了溶血和细胞毒性评估。结果表明，所提出的化合物具有非溶血特性，并对鳞状细胞癌（A431 细胞系）表现出有趣的细胞毒性活性，这种活性与这些 β-内酰胺的结构和浓度密切相关。在测试的分子中，2b 的细胞毒性最强，IC50 值最低（30-47 µg/mL），与非肿瘤细胞相比，它对肿瘤细胞具有良好的选择性。
• Photocatalytic organosulfur reagent-promoted selective mono-(deutero)hydrodechlorination
  作者：Junlei Wang、Guocheng Gao、Jiadong Cheng、Jintao Li、Xiaoshuang Chen、Xuemei Chen、Daohai Zhang、Hongqing Li、Xiaohua Cai、Binbin Huang

  DOI：10.1039/d4gc01173b

  日期：——

  partial C–Cl bond reduction represents an important strategy for the construction of valuable chlorine-containing skeletons. Herein, we report an efficient and straightforward mono-(deutero)hydrodechlorination strategy of various trichloroacetyl esters and amides for the incorporation of gem-dichloromethyl moieties. The proposed mechanism involves key electron donor–acceptor (EDA) complexes formed between

  选择性部分C-Cl键还原是构建有价值的含氯骨架的重要策略。在此，我们报告了各种三氯乙酰酯和酰胺的有效且简单的单（氘）氢脱氯策略，用于掺入偕二氯甲基部分。所提出的机制涉及催化环己硫醇（CySH）和底物之间形成的关键电子供体-受体（EDA）复合物，该复合物在蓝光照射下经历单电子转移（SET）过程，提供宝石-二氯自由基阴离子和CyS˙。克级反应和生物活性分子的后期修饰进一步证明了该方法的潜在效用。
• Controlling Selectivity in the Synthesis of <i>Z</i> ‐α,β‐Unsaturated Amidines by Tuning the <i>N</i> ‐Sulfonyl Group in a Rhodium(II) Catalyzed 1,2‐H Shift
  作者：Matthew L. Martin、Alistair Boyer

  DOI：10.1002/ejoc.202101235

  日期：2021.11.22

  α,β-Unsaturated amidines can be synthesized in high yield by rhodium(II) carboxylate catalyzed 1,2-H shift following denitrogenation of α-diazo amidines. Using a large carboxylate rhodium(II) ligand and an electron-poor N-sulfonyl group results in exclusive Z-selectivity and excellent yield by suppressing side reactions involving intramolecular oxygen transfer.

  α-重氮脒脱氮后，羧酸铑（II）催化1,2-H转变，可以高产率合成α,β-不饱和脒。通过抑制涉及分子内氧转移的副反应，使用大的羧酸铑 (II) 配体和缺电子的N-磺酰基可实现独特的Z-选择性和优异的产率。
• Dearomative radical spirocyclization from N-ce:raghubenzyltrichloroacetamides revisited using a copper(I)-mediated atom transfer reaction leading to 2-azaspiro[4.5]decanes
  作者：Faïza Diaba、Juan A. Montiel、Agustín Martínez-Laporta、Josep Bonjoch

  DOI：10.1016/j.tetlet.2013.03.019

  日期：2013.5

  An atom transfer radical dearomatizing spirocyclization from N-benzyltrichloroacetamides using CuCl regioselectively leads to 2-azaspiro[4.5]decadienes, in which the labile allylic chlorine atom is easily replaced by a hydroxyl group in aqueous medium or by quenching with methanol or allylamine. After oxidation of the target compound, the N-tert-butyl group can be removed from the resulting spirocyclohexanedienone. (c) 2013 Elsevier Ltd. All rights reserved.