para-Methoxybenzyltrichloroacetimidate | 152480-59-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: para-Methoxybenzyltrichloroacetimidate
• 英文别名: 2,2,2-trichloro-N'-[(4-methoxyphenyl)methyl]ethanimidamide
• CAS: 152480-59-6
• 化学式: C₁₀H₁₁Cl₃N₂O
• 分子量: 281.569
• InChiKey: VQFMOCXNMGFKNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  para-Methoxybenzyltrichloroacetimidate 在 chromium dichloride 、 sodium periodate 、 lithium aluminium tetrahydride 、 三氟甲磺酸 、 camphor-10-sulfonic acid 、 potassium hydride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 35.0h， 生成 (+)-(Z)-(2S,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethylocta-5,7-dien-1-ol
  参考文献：
  名称：

  使用手性酮的硼介导的醛醇缩合反应合成抗微管剂（+）-Discodermolide。

  摘要：

  具有与紫杉醇相似的作用机理，标题化合物1是癌症化学疗法发展中特别有希望的候选者。这种基于立体控制的醛醇缩合反应的有效合成方法应有助于克服稀有海绵来源的稀缺天然物质1的供应。

  DOI：

  10.1002/(sici)1521-3773(20000117)39:2<377::aid-anie377>3.0.co;2-e
• 作为产物：
  描述：

  4-甲氧基苄胺 、 三氯乙腈 以 neat (no solvent) 为溶剂， 反应 0.08h， 生成 para-Methoxybenzyltrichloroacetimidate
  参考文献：
  名称：

  苯并噻二嗪官能-1,1-二氧化物衍生物的合成通过分子内Ç的trichloroacetamidine和苯磺酰氯ħ活化反应

  摘要：

  通过三氯乙腈，苯磺酰氯和各种伯胺的新型三组分分子内C H活化反应，可以实现功能化的苯并噻二嗪1,1-二氧化物衍生物的合成。该反应在室温下在四氢呋喃中在催化铜（I）和1-脯氨酸作为配体存在下进行。

  DOI：

  10.1016/j.tetlet.2018.04.038

文献信息

• A new route for the synthesis of functionalized benzo[d]imidazo[5,1-b]thiazol-1-amine derivatives from benzothiazole, trichloroacetamidines and terminal alkynes
  作者：Maryam Bayanati、Niloofar Parizadeh、Manijeh Nematpour、Anna Sedaghat、Sayyed Abbas Tabatabaia

  DOI：10.1080/17415993.2020.1820010

  日期：2021.3.4

  A novel class of substituted benzo[d]imidazo[5,1-b]thiazol-1-amine derivatives was synthesized utilizing a one-pot Cu-catalyzed cycloaddition of benzothiazole, trichloroacetonitrile, various amines and terminal alkynes in acetonitrile at room temperature. The speed of this simple four-component reaction along with mild conditions, high yields, readily available starting materials, the ease of work-up

  在室温下，利用一锅铜催化的苯并噻唑，三氯乙腈，各种胺和末端炔烃的一锅铜催化合成了一类新型的取代苯并[d]咪唑并[5,1-b]噻唑-1-胺衍生物。这种简单的四组分反应的速度以及温和的条件，高收率，易于获得的起始原料，无需使用污染性贵金属催化剂即可进行后处理的简便性以及柱色谱法是本方法的重要特征。
• Design, synthesis and anti-diabetic activity of novel 1, 2, 3-triazole-5-carboximidamide derivatives as dipeptidyl peptidase-4 inhibitors
  作者：Hossein Fasihi Dastjerdi、Nima Naderi、Manijeh Nematpour、Elham Rezaee、Mohammad Mahboubi-Rabbani、Melika Ebrahimi、Samaneh Hosseinipoor、Omid Hosseini、Sayyed Abbas Tabatabai

  DOI：10.1016/j.molstruc.2020.128745

  日期：2020.12

  the treatment of type 2 diabetes mellitus. In this study, a novel series of 1, 2, 3-triazole-5-carboximidamide derivatives were designed, synthesized, and inhibitory activity evaluated against the DPP-4 enzyme. All of the compounds represented inhibitory activity, and among them, compounds 6a, 6b, and 6c showed desirable inhibitory activity of DPP-4 with IC50 values of 14.75 nM, 6.75 nM, and 6.57 nM

  摘要 4 型二肽基肽酶 (DPP-4) 抑制剂作为一种有效的胰岛素分泌刺激剂和胰腺分泌胰高血糖素的抑制剂，已被认为是治疗 2 型糖尿病的有前途的药物。在这项研究中，设计、合成了一系列新的 1, 2, 3-triazole-5-carboximidamide 衍生物，并评估了对 DPP-4 酶的抑制活性。所有化合物均表现出抑制活性，其中化合物6a、6b和6c显示出理想的DPP-4抑制活性，IC50值分别为14.75 nM、6.75 nM和6.57 nM。在 NMRI 小鼠的 OGTT 期间，10 mg/kg 剂量的化合物 6a 显示葡萄糖耐量增强。而且，
• Facile and Efficient Synthesis of New Class of Imidazole Derivatives via One-Pot Multicomponent Reactions in Water
  作者：Zinatossadat Hossaini、Samereh Seyfi、Faramarz Rostami-Charati、Mehdi Ghambarian

  DOI：10.2174/13862073113169990046

  日期：2013.11

  A water-accelerated multicomponent synthesis of organic target molecules has been used as a key method for the preparation of novel imidazole derivatives. The three-component condensation reactions of primary amines with trichloroacetonitrile in the presence of ninhydrine in water are developed as efficient and clean green synthetic procedures for the high-yielding preparation of imidazoles.

  有机靶分子的水促进多组分合成已被用作制备新型咪唑衍生物的关键方法。在水中存在茚三酮的情况下，伯胺与三氯乙腈的三组分缩合反应被开发为高效，清洁的绿色合成方法，用于高产率地制备咪唑。
• Trichloroacetamidines, a new class of positive inotropic agents
  作者：Walfred S. Saari、Mark B. Freedman、Joel R. Huff、Stella W. King、Andrew W. Raab、Susan J. Bergstrand、Edward L. Engelhardt、Alexander Scriabine、George Morgan

  DOI：10.1021/jm00210a021

  日期：1978.12

  A series of trichloroacetamidine derivatives, obtained by addition of amines to trichloroacetonitrile, was evaluated for positive inotropic activity on isolated cat heart papillary muscles. Increased contractility, not antagonized by beta-adrenergic blockade with sotalol or reserpine pretreatment, was observed in this assay with a variety of N-substituted trichloroacetamidine derivatives. More extensive pharmacological studies with the 3-indolylmethyl analogue 2 showed that this amidine in dogs, 5 mg/kg iv, produced a positive inotropic effect more pronounced than that of ouabain, 50 microgram/kg iv. Several of the trichloroacetamidines were found to be inhibitors of guinea pig kidney and calf heart Na-K-dependent ATPase and to have specificity for these enzymes different from that of ouabain. Bacterial mutagenic activity was observed with three members, 2,3, and 12, of the series.
• An approach to substituted dihydroisoquinolin-1(2H)-ones from Baylis–Hillman adducts
  作者：Fernando Coelho、Demetrius Veronese、Elizandra C.S Lopes、Rodrigo C Rossi

  DOI：10.1016/s0040-4039(03)01307-8

  日期：2003.7

  In this communication we describe an easy and straightforward alternative method for the preparation of 3,4-substituted isoquinolin-1(2H)-ones, using Baylis-Hillman adducts as starting material. (C) 2003 Elsevier Ltd. All rights reserved.