2,4-二氯苄氧胺盐酸盐 | 52370-40-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2,4-二氯苄氧胺盐酸盐
• 中文别名: O-2,4-二氯基苄氧胺盐酸盐；2,4-二氯苄氧胺
• 英文名称: 2,4-Dichlorbenzyloxyamin
• 英文别名: O-(2,4-Dichlorobenzyl)hydroxylamine；O-[(2,4-dichlorophenyl)methyl]hydroxylamine
• CAS: 52370-40-8
• 化学式: C₇H₇Cl₂NO
• 分子量: 192.045
• InChiKey: RWUMUUIIAOFEFC-UHFFFAOYSA-N

物化性质

• 沸点：
  306.1±32.0 °C(Predicted)
• 密度：
  1.374

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2922199090

制备方法与用途

制备方法

用于医药、农药以及抗菌剂的生产过程中的中间体。

用途简介

暂无具体内容。

反应信息

• 作为反应物：
  描述：

  2,4-二氯苄氧胺盐酸盐 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 72.0h， 生成 1-[(氨基氧基)甲基]-2,4-二氯苯盐酸盐
  参考文献：
  名称：

  Synthesis and Fungicidal Activity of Macrolactams and Macrolactones with an Oxime Ether Side Chain

  摘要：

  Three series of novel macrolactams and macrolactones - 12-alkoxyimino-tetradecanlactam, 12-alkoxyiminopentadecanlactam, and 12-alkoxyiminodecanlactone derivatives (7A, 7B, and 7C) - were synthesized from corresponding 12-oxomacrolactams and 12-oxomacrolactone. Their structures were confirmed by H-1 NMR and elemental analysis. The Z and E isomers of 7A and 7B were separated, and their configurations were determined by H-1 NMR. These compounds showed fair to excellent fungicidal activities against Rhizoctonia solani Kuhn. It is interesting that the Z and E isomers of most of the compounds have quite different fungicidal activities. The fact that the compounds have a gradual increase of fungicidal activity in the order of 7A, 7C, and 7B indicated that the macrocyclic derivatives with a hydrogen-bonding acceptor (=N-O-) and a hydrogen-bonding donor (-CONH-) on the ring, and a three methylenes distance (CH2CH2CH2) between these two functional groups, exhibited the best fungicidal activity. The bioassay also showed that 7B not only has good fungicidal activity but also may have a broad spectrum of fungicidal activities.

  DOI：

  10.1021/jf072733+
• 作为产物：
  描述：

  2,4-二氯苄醇 在 偶氮二甲酸二异丙酯 、 一水合肼 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 2,4-二氯苄氧胺盐酸盐
  参考文献：
  名称：

  O-alkylhydroxylamines as rationally-designed mechanism-based inhibitors of indoleamine 2,3-dioxygenase-1

  摘要：

  Indoleamine 2,3-dioxygenase-1 (IDO1) is a promising therapeutic target for the treatment of cancer, chronic viral infections, and other diseases characterized by pathological immune suppression. Recently important advances have been made in understanding IDO1's catalytic mechanism. Although much remains to be discovered, there is strong evidence that the mechanism proceeds through a heme-iron bound alkylperoxy transition or intermediate state. Accordingly, we explored stable structural mimics of the alkylperoxy species and provide evidence that such structures do mimic the alkylperoxy transition or intermediate state. We discovered that O-benzylhydroxylamine, a commercially available compound, is a. potent sub-micromolar inhibitor of IDO1. Structure activity studies of over forty derivatives of O-benzylhydroxylamine led to further improvement in inhibitor potency, particularly with the addition of halogen atoms to the meta position of the aromatic ring. The most potent derivatives and the lead, O-benzylhydroxylamine, have high ligand efficiency values, which are considered an important criterion for successful drug development. Notably, two of the most potent compounds demonstrated nanomolar-level cell-based potency and limited toxicity. The combination of the simplicity of the structures of these compounds and their excellent cellular activity makes them quite attractive for biological exploration of IDO1 function and antitumor therapeutic applications. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.12.028

文献信息

• Synthesis of 3-Amino(alkoxy)-2,4-dioxo-1,3-oxazolidine-5-carboxylates from Tartronic Esters
  作者：Thomas Kurz、Detlef Geffken

  DOI：10.1515/znb-1999-0516

  日期：1999.5.1

  The reaction of tartronic esters (1a-d) with 1,1'-carbonyl-di-(1,2,4-triazole), hydrazines or hydroxylamines produces 3-amino/3-alkoxy(aralkoxy)-2,4-dioxo-1,3-oxazolidine-5-carboxylic esters (5,6) which are structurally related to the fungicides Famoxadone (I) and Chlozolinate (II). Under suitable conditions the carboxylic ester of 6 can be converted to a carboxamide (7), carbohydrazide (8) or carbohydroxamic acid (9).

  酒石酸酯（1a-d）与1,1'-羰基二-(1,2,4-三唑), 肼或羟胺的反应产生结构相关于杀菌剂Famoxadone（I）和Chlozolinate（II）的3-氨基/3-烷氧（芳基氧）-2,4-二氧杂环-1,3-噁唑啉-5-羧酸酯（5,6）。在适当条件下，6的羧酸酯可以转化为羧酰胺（7）、羧基肼（8）或羧基羟肟酸（9）。
• Synthesis of anthelmintically activeN-methylated amidoxime analogues of the cyclic octadepsipeptide PF1022A
  作者：Peter Jeschke、Achim Harder、Georg von Samson-Himmelstjerna、Winfried Etzel、Wolfgang Gau、Gerhard Thielking、Gerhard Bonse

  DOI：10.1002/ps.590

  日期：2002.12

  product PF1022A. In particular an improved efficacy against Haemonchus contortus Rudolphi and Trichostrongylus colubriformis Giles in sheep compared to the potent cyclic octadepsipeptide PF1022A and its mono-thionated derivative has been observed. Here we report on a specific modification at the N-methyl amide linkage by using the mono-thionated PF1022A, resulting in novel anthelmintically active backbone

  环状十八肽PF1022A的N-甲基化a胺肟类似物代表新型衍生物，具有体外抗旋毛虫欧文和巴西柔毛夜蛾活性，并具有抗小鼠和绵羊寄生线虫的活性。与天然产物PF1022A相比，它们中的一些在小鼠中表现出更好的抗Hymenolepis nana Siebold，Spterosa Schneider和Heligmosomoides polygyrus Dujardin活性。尤其是，与强效的环八肽肽PF1022A及其单亚硫代衍生物相比，已观察到对绵羊的弯曲变形金丝猴（Ruemonphi Rutorphi）和毛细线虫（Trichostrongylus colubriformis Giles）有改善的功效。在这里，我们报告了通过使用单亚硫代PF1022A在N-甲基酰胺键处的特定修饰，从而产生了PF 1022A的新型具有抗炎活性的骨架类似物。
• 2-(4,6-dimethoxy-2-pyrimidinyloxy)benzaldoximes, preparation processes
  申请人：Mitsui Toatsu Chemicals, Incorporated

  公开号：US04986846A1

  公开（公告）日：1991-01-22

  Disclosed are herbicidally active pyrimidine derivatives of the formula ##STR1## wherein R represents a hydrogen atom or an etherifying group, e.g., a lower alkyl, lower alkenyl, lower alkynyl, phenyl-substituted lower alkenyl, lower haloalkenyl, cycloalkyl, substituted phenyl-substituted lower alkenyl or phenyl-substituted lower alkynyl group; or a group represented by the following formula: ##STR2## wherein R.sup.1 represents a hydrogen atom or a lower alkyl group, X a halogen atom or a lower alkyl or lower alkoxyl group, m and n individually 0-2, and when m is 2, both Xs may be the same or different, and herbicidal compositions containing the same, alone or in combination with another herbicidally active compound, the pyrimidine derivatives being prepared by reaction of 2-(4,6-dimethoxy-2-pyrimidinyloxy)benzaldehyde with NH.sub.2 OR or with a salt of hydroxylamine followed by reaction with a halide of the formula RY wherein R has the same value as above and Y is Cl, Br or I.

  揭示了具有以下式的除草活性嘧啶衍生物##STR1##其中R代表氢原子或醚化基团，例如，较低的烷基，较低的烯基，较低的炔基，苯基取代的较低烯基，较低的卤代烯基，环烷基，取代的苯基取代的较低烯基或苯基取代的较低炔基；或由以下式表示的基团：##STR2##其中R.sup.1代表氢原子或较低的烷基，X代表卤原子或较低的烷基或较低的烷氧基，m和n分别为0-2，当m为2时，两个X可能相同或不同，并且含有这些衍生物的除草组合物，单独或与另一种除草活性化合物结合使用，所述嘧啶衍生物通过2-(4,6-二甲氧基-2-嘧啶氧基)苯甲醛与NH.sub.2 OR或与羟胺盐反应，然后与具有上述相同值的R的卤化物RY反应，其中Y为Cl，Br或I制备而成。
• Synthesis, Crystal Structure, Herbicidal Activity, and SAR Study of Novel <i>N</i>-(Arylmethoxy)-2-chloronicotinamides Derived from Nicotinic Acid
  作者：Chen-Sheng Yu、Qiao Wang、Joanna Bajsa-Hirschel、Charles L. Cantrell、Stephen O. Duke、Xing-Hai Liu

  DOI：10.1021/acs.jafc.0c07538

  日期：2021.6.16

  animals. To discover novel natural-product-based herbicides, a series of N-(arylmethoxy)-2-chloronicotinamides were designed and synthesized. Some of the new N-(arylmethoxy)-2-chloronicotinamides exhibited excellent herbicidal activity against Agrostis stolonifera (bentgrass) at 100 μM. Compound 5f (2-chloro-N-((3,4-dichlorobenzyl)oxy)nicotinamide) possessed excellent herbicidal activity against Lemna paucicostata

  烟酸又称烟酸，是一种天然产物，广泛存在于动植物中。为了发现基于天然产物的新型除草剂，设计并合成了一系列N- (芳基甲氧基)-2-氯代烟酰胺。一些新的N -(芳基甲氧基)-2-氯烟酰胺在 100 μM 时对Agrostis stolonifera（蓼蒿）表现出优异的除草活性。化合物5F（2-氯- ñ - （（3,4-二氯苄基）氧基）烟酰胺）具有优良的除草活性对青萍（浮萍），与IC 50值 7.8 μM，而商业除草剂异恶草酮和丙苯腈的值分别为 125 和 2 μM。本文报道的构效关系可用于开发抗单子叶杂草的新型除草剂。
• Design and Synthesis of Terephthalic Acid‐Based Histone Deacetylase Inhibitors with Dual‐Stage Anti‐<i>Plasmodium</i>Activity
  作者：Katharina Stenzel、Ming Jang Chua、Sandra Duffy、Yevgeniya Antonova‐Koch、Stephan Meister、Alexandra Hamacher、Matthias U. Kassack、Elizabeth Winzeler、Vicky M. Avery、Thomas Kurz、Katherine T. Andrews、Finn K. Hansen

  DOI：10.1002/cmdc.201700360

  日期：2017.10.9

  work we aimed to develop parasite‐selective histone deacetylase inhibitors (HDAC) inhibitors with activity against the disease‐causing asexual blood stages of Plasmodium as well as causal prophylactic and/or transmission blocking properties. We report the design, synthesis, and biological testing of a series of 13 terephthalic acid‐based HDAC inhibitors. All compounds showed low cytotoxicity against

  在这项工作中，我们旨在开发具有选择性的寄生虫选择性组蛋白脱乙酰基酶抑制剂（HDAC）抑制剂，该抑制剂对引起疾病的无性疟原虫血液阶段具有活性，并具有因果预防和/或传播阻断特性。我们报告了一系列13种基于对苯二甲酸的HDAC抑制剂的设计，合成和生物学测试。所有化合物显示出对人胚胎肾（HEK293）细胞的细胞毒性低（IC 50：8-> 51μ米）中，用11还具有亚微摩尔的体外活性对药物敏感（3D7）和多药耐药（DD2）无性血液阶段的恶性疟原虫寄生虫（IC 50 ≈0.1-0.5μ米）。检查了一部分化合物对早期和晚期恶性疟原虫配子细胞和伯氏疟原虫外红细胞阶段寄生虫的活性。虽然仅观察到对配子细胞的中等活性（IC 50 > 2μm），但活性最高的化合物（N 1 -（（3,5-二甲基苄基）氧基）N 4-羟基对苯二甲酰胺1 f）表现出对微配子的亚微摩尔活性。伯氏疟原虫红细胞外阶段（IC 50 0.18μ米为比HepG2细胞红细胞外的形式）和>