N-hydroxy-3,4,5-trimethoxybenzimidoyl chloride | 105677-86-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-hydroxy-3,4,5-trimethoxybenzimidoyl chloride
• 英文别名: 3,4,5-trimethoxybenzohydroximoyl chloride；N-Hydroxy-3,4,5-trimethoxybenzimidoyl Chloride；N-hydroxy-3,4,5-trimethoxybenzenecarboximidoyl chloride
• CAS: 105677-86-9
• 化学式: C₁₀H₁₂ClNO₄
• 分子量: 245.663
• InChiKey: SJDHUOLOOCBDHF-UHFFFAOYSA-N

物化性质

• 熔点：
  138-139 °C
• 沸点：
  380.4±52.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  60.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-硫代-b-D-葡萄糖四乙酸酯 、 N-hydroxy-3,4,5-trimethoxybenzimidoyl chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到2,3,4,6-tetra-O-acetyl-1-S-(Z)-3,4,5-trimethoxybenzohydroximoyl-1-thio-β-D-glucopyranose
  参考文献：
  名称：

  葡萄糖基螺旋杂环作为糖原磷酸化酶的有效抑制剂

  摘要：

  通过NBS介导的相应的葡糖基-羟肟基硫代酸酯的螺环化，可以高收率制备葡糖基亚烷基-螺-1,4,2-氧杂噻唑。为了合成具有氮原子而不是硫原子的类似的吡喃吡喃基-螺-1,2,4-恶二唑啉，尝试的环化导致杂环的芳构化并带有吡喃糖基环。酶促测量表明，一些基于葡萄糖的抑制剂在微摩尔范围内具有活性。在 迄今为止已知的基于葡萄糖的抑制剂中，2-萘基取代的1,4,2-氧杂噻唑显示出对RMGPb的最佳抑制作用（K i = 160 nM）。

  DOI：

  10.1016/j.bmc.2009.05.080
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛肟 在 N-(tert-butyl)-N-chloro-cyanamide 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到N-hydroxy-3,4,5-trimethoxybenzimidoyl chloride
  参考文献：
  名称：

  A novel one-pot synthesis of hydroximoyl chlorides and 2-isoxazolines using N-tert-butyl-N-chlorocyanamide

  摘要：

  Treatment of aldoximes with N-tert-butyl-N-chlorocyanamide gave hydroximoyl chlorides in quantitative yields in less than a minute, which on dehydrohalogenation in the presence of triethylamine gave the corresponding nitrile oxides. The nitrile oxides underwent 1,3-dipolar addition to dipolarophiles and gave 2-isoxazolines in excellent yields under mild conditions. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.12.083

文献信息

• Stereoconvergent and stepwise 1,3-dipolar cycloadditions of nitrile oxides and nitrile imines
  作者：Zhenni Zhao、Zhi Ou、Subarna Jyoti Kalita、Feng Cheng、Qian Huang、Yangyi Gu、Yuhao Wang、Yan Zhao、Yiyong Huang

  DOI：10.1016/j.cclet.2021.12.006

  日期：2022.6

  stereoconvergent 1,3-dipolar cycloaddition of nitrile oxides and nitrile imines with E/Z isomeric mixture of electron-deficient olefins is reported, delivering isoxazolines and pyrazolines bearing two vicinal stereogenic tertiary and trifluoromethylated quaternary carbon centers with perfect regio- and diastereoselectivities. The possibility of concerted cycloaddition/epimerization sequence under basic

  报道了腈氧化物和腈亚胺与缺电子烯烃的E / Z异构体混合物的立体收敛 1,3-偶极环加成的第一个例子，提供了带有两个邻位立体叔和三氟甲基化季碳中心的异恶唑啉和吡唑啉，具有完美的区域和非对映选择性。通过一些对照实验和DFT计算，排除了在碱性条件下协同环加成/差向异构序列形成热力学稳定的非对映异构体的可能性，并提出了逐步机理。
• Norcantharidin analogues — Synthesis and evaluation of growth inhibition in a panel of selected tumor-cell lines
  作者：Liping Deng、Li Shen、Jing Zhang、Bo Yang、Qiaojun He、Yongzhou Hu

  DOI：10.1139/v07-082

  日期：2007.11.1

  A series of norcantharidin (NCTD) analogues have been synthesized by [3+2]1,3-dipolar cycloaddition reaction of norcantharidin derivatives of substituted aromatic amines with four nitrile oximes. All analogues have been screened for their antiproliferative activity in vitro against a panel of tumor cell lines: KB, SGC-7901, HL60, Bel-7402, HO-8910, and ECA109, producing IC₅₀ values from 0.36 µmol/L to >100 µmol/L. Compound 9d showed potency for the treatment of hepatoma, with IC₅₀ value to Bel-7402 cell line comparable to that of norcantharidin.Key words: norcantharidin analogues, isoxazoline, growth inhibition.

  通过取代芳香胺的去甲蒽醌衍生物与四种腈肟的［3+2］1,3-二极环加成反应，合成了一系列去甲蒽醌（NCTD）类似物。对所有类似物进行了体外抗肿瘤细胞系增殖活性筛选：这些化合物的 IC50 值从 0.36 µmol/L 到 100 µmol/L。化合物9d显示出治疗肝癌的效力，对Bel-7402细胞株的IC50值与去甲斑蝥素相当。
• A convenient synthesis of benzohydroximoyl chlorides as nitrile oxide precursors by hydrogen chloride/N,N-dimethylformamide/oxone system
  作者：Jae Nyoung Kim、Eung K. Ryu

  DOI：10.1021/jo00050a054

  日期：1992.11
• Novel spirobicyclic artemisinin analogues (artemalogues): Synthesis and antitumor activities
  作者：Gang Liu、Shanshan Song、Shiqi Shu、Zehong Miao、Ao Zhang、Chunyong Ding

  DOI：10.1016/j.ejmech.2015.08.035

  日期：2015.10

  The sesquiterpene lactone framework of artemisinin was used as a drug repositioning prototype for the development of novel antitumor drugs. Several series of novel artemisinin analogues (artemalogues) were designed and synthesized through 1,3-dipolar cycloaddition of artemisitene with nitrile oxides or nitrones. The isoxazolidine-containing spirobicyclic artemalogue 11b turns out to be the most potent with low micromolar IC50 values against all three tumor cells, which were at least 4- to 14-fold more potent than the parent artemisinin. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Regioselective synthesis of C-nucleosides by 1,3-dipolar cycloaddition of arylnitrile oxides to 5,6-dideoxy-1,2-O-iso-propylidene-α-d-xylo-hex-5-enofuranose
  作者：Usama A. R. Al-Timari、Ľubor Fišera

  DOI：10.1016/0008-6215(91)84091-r

  日期：1991.9