3-羟基呋喃丹-7-酚 | 17781-15-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 中文名称: 3-羟基呋喃丹-7-酚
• 中文别名: 3-羟基-7-酚-克百威,10ΜG/ΜL于乙酸乙酯；3-羟基-7-酚-克百威, 1ΜG /ΜL于乙酸乙酯
• 英文名称: 2,3-dihydro-3-hydroxy-2,2-dimethylbenzofuran-7-ol
• 英文别名: 2,3-dihydro-2,2-dimethyl-3,7-benzofurandiol；2,3-dihydro-2,2-dimethylbenzofuran-3,7-diol；3,7-dihydroxy-2,2-dimethylbenzofuran；3-Hydroxycarbofuran phenol；3-hydroxy-7-phenolcarbofuran；3,7-Benzofurandiol, 2,3-dihydro-2,2-dimethyl-；2,2-dimethyl-3H-1-benzofuran-3,7-diol
• CAS: 17781-15-6
• 化学式: C₁₀H₁₂O₃
• mdl: MFCD00155427
• 分子量: 180.203
• InChiKey: CNFFSKAZCVPTPA-UHFFFAOYSA-N

物化性质

• 熔点：
  107 - 111°C
• 沸点：
  292.4±40.0 °C(Predicted)
• 密度：
  1.256±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）
• 保留指数：
  1423.3

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  克百威 在 chromium(VI) oxide 、 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成 3-羟基呋喃丹-7-酚
  参考文献：
  名称：

  细胞色素P450催化的杀虫剂代谢的化学模型。在氨基甲酸酯类杀虫剂的氧化代谢中的应用。

  摘要：

  细胞色素P450（CP450）催化了呋喃丹（1），西维因（2）和吡虫威（3）的氧化代谢，已通过四芳基铁卟啉铁（III）催化的仿生氧化进行了建模。通过比较在标准条件下测定的代谢物的HPLC保留时间，鉴定出1的氧化产物，并通过（1）H和（13）C NMR光谱对其进行表征。产品分布与体内代谢特征的比较表明，H（2）O（2）/间四（五氟苯基）卟啉氯化铁（III）[Fe（TF（20）PP）]系统模仿了昆虫CP450的作用。反对呋喃丹。通过HPLC /电喷雾MS监测的其他氨基甲酸酯类杀虫剂（2和3）的仿生氧化进一步证明了该系统的有效性。将该仿生模型的预测能力与基于知识的专家系统的预测能力进行了比较。尽管最近在药物研究中采用了类似的模型，但这种方法的有效性已首先证明可用于预测农用化学品的代谢状况。

  DOI：

  10.1021/jf980347+

文献信息

• Metabolism of carbosulfan II. Human interindividual variability in its in vitro hepatic biotransformation and the identification of the cytochrome P450 isoforms involved
  作者：Khaled Abass、Petri Reponen、Sampo Mattila、Olavi Pelkonen

  DOI：10.1016/j.cbi.2010.03.024

  日期：2010.5

  This study aims to characterize interindividual variability and individual CYP enzymes involved in the in vitro metabolism of the carbamate insecticide carbosulfan. Microsomes from ten human livers (HLM) were used to characterize the interindividual variability in carbosulfan activation. Altogether eight phase I metabolites were analyzed by LC–MS. The primary metabolic pathways were detoxification

  这项研究的目的是表征氨基甲酸酯杀虫剂碳硫丹的体外代谢中涉及的个体间变异性和单个CYP酶。使用来自十个人肝的微粒体（HLM）来表征硫丹活化的个体间差异。LC-MS分析了总共八种I期代谢物。主要的代谢途径是通过将硫最初氧化为碳硫丹亚磺酰胺而解毒（“硫氧化途径”），并通过裂解氮硫键（NS）进行活化以产生呋喃呋喃和二丁胺（“呋喃呋喃途径”）。HLM的最大和最小硫丹活化值之间的差异表明k m，V中的变异性接近5.9、7.0和6.6倍max和CL int值分别。CYP3A5和CYP2B6形成碳硫丹亚磺酰胺的效率最高，而CYP3A4和CYP3A5生成碳氢呋喃代谢途径的效率最高。根据人体肝脏中CYP酶的平均丰度，CYP3A4贡献了98％的硫丹活化，而CYP3A4和CYP2B6分别贡献了57％和37％的排毒作用。丁硫克百威活化和CYP标记活性之间的相关性显著被视为与CYP3A4（奥美拉唑磺化氧化），CYP2
• Influence of anionic and nonionic micelles upon hydrolysis of 3-hydroxy-carbofuran
  作者：G. Astray、A. Cid、J. A. Manso、J. C. Mejuto、O. Moldes、J. Morales

  DOI：10.1002/kin.20563

  日期：2011.8

  The effect of nonionic and anionic micelles upon the stability of 3‐hydroxy‐carbofuran in basic media has been studied. The presence of micelles in the reaction medium implies a large inhibition of the basic hydrolysis of 3‐hydroxy‐carbofuran, due to the association of 3‐hydroxy‐carbofuran with the micellar core. The kinetic constants for the basic hydrolysis in these microheterogeneous media have

  研究了非离子和阴离子胶束对3-羟基卡夫呋喃在碱性介质中稳定性的影响。由于3-羟基卡夫呋喃与胶束核心的缔合，因此反应介质中胶束的存在对3-羟基卡夫呋喃的基本水解有很大的抑制作用。这些微非均质介质中碱性水解的动力学常数是根据胶束假相模型获得的。©2011 Wiley Periodicals，Inc.国际化学杂志Kinet 43：402–408，2011
• Competitive Degradation and Detoxification of Carbamate Insecticides by Membrane Anodic Fenton Treatment
  作者：Qiquan Wang、Ann T. Lemley

  DOI：10.1021/jf034311f

  日期：2003.8.1

  The competitive degradation of six carbamate insecticides by membrane anodic Fenton treatment (AFT), a new Fenton treatment technology, was carried out in this study. The carbamates studied were dioxacarb, carbaryl, fenobucarb, promecarb, bendiocarb, and carbofuran. The results indicate that AFT can effectively degrade these insecticides in both single component and multicomponent systems. The carbamates compete for hydroxyl radicals, and their kinetics obey the previously developed AFT kinetic model quite well. Hydroxyl radical reaction rate constants were obtained, and they decrease in the following order: dioxacarb approximate to carbaryl > fenobucarb > promecarb > bendiocarb > carbofuran. The AFT is shown to have higher treatment efficiency at higher temperature. Degradation products of the carbamates were determined by gas chromatography/mass spectrometry, and it appears that degradation can be initiated by hydroxyl radical attack at different sites in the molecule, depending on the individual structure of the compound. Substituted phenols are the commonly seen degradation products. The AFT treatment can efficiently remove the chemical oxygen demand of the carbamate mixture, significantly increasing the biodegradability. Earthworm studies show that the AFT is also an effective detoxification process.

表征谱图