4-羟基甲基-2-碘-6-甲氧基苯酚 | 37987-21-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 4-羟基甲基-2-碘-6-甲氧基苯酚
• 英文名称: 4-hydroxy-3-iodo-5-methoxybenzyl alcohol
• 英文别名: 5-Iodvanillylalkohol；3-iodo-4-hydroxy-5-methoxybenzenemethanol；4-(Hydroxymethyl)-2-iodo-6-methoxyphenol
• CAS: 37987-21-6
• 化学式: C₈H₉IO₃
• mdl: MFCD00238615
• 分子量: 280.062
• InChiKey: YQQRUTNMNAZIAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2909500000

反应信息

• 作为反应物：
  描述：

  4-羟基甲基-2-碘-6-甲氧基苯酚 在 氧气 、 copper(l) chloride 作用下， 以 二甲基亚砜 为溶剂， 生成 5-碘香兰素
  参考文献：
  名称：

  Darstellung und Oxydation von Hydroxybenzylalkoholen

  摘要：

  DOI：

  10.1007/bf00905194
• 作为产物：
  描述：

  5-碘香兰素 在 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 4-羟基甲基-2-碘-6-甲氧基苯酚
  参考文献：
  名称：

  具有立体中心和轴的内酯的非动态和动态动力学分辨率：Herbertenediol 和 Mastigophorenes A 和 B 的立体选择性全合成

  摘要：

  描述了倍半萜烯二醇 (3) 及其天然二聚体，mastigophorenes A [(P)-1] 和 B [(M)-1] 的立体选择性全合成。遵循“内酯概念”，联芳基轴上的构型通过构型不稳定的联合联芳基内酯前体 17 的立体控制还原环裂解（非对映异构体比例高达 97:3）被atropo-divergently 诱导为 P 或可选的 M使用氧杂硼烷-硼烷系统，通过动态动力学拆分。内酯偶联的机理考虑表明卤素取代基旁边的甲氧基的干扰，导致偶联产率从 39% 提高到 87%（得到内酯 37）。作为内酯方法的一种新的、同样高效的变体，我们首次报告了结构相关但中心手性的“脂肪族-芳香族”内酯 (rac)-10 的非动态动力学分辨率。其高效 (krel > 300) 对映异构体差异化 Corey-Ba...

  DOI：

  10.1021/ja001455r

文献信息

• Chromanes and their pharmaceutical compositions and methods
  申请人：Hoffmann-La Roche Inc.

  公开号：US05015661A1

  公开（公告）日：1991-05-14

  Racemic Compounds of the formula ##STR1## A is --C.tbd.C--R.sub.6, --CH.sub.2 --CH.sub.2 --R.sub.7 or ##STR2## R.sub.1 is hydrogen or lower alkanoyl, R.sub.2, R.sub.3, and R.sub.4 independently are hydrogen or lower alkyl, R.sub.5 is lower alkyl, R.sub.6 is a heteroaromatic radical or an aromatic radical selected from phenyl, naphthyl or phenanthryl, which aromatic radical may optionally be substituted by one or more substituents selected from chlorine, fluorine, lower alkyl, lower alkoxy, phenyl lower alkoxy, lower alkanoyl, lower alkanoyloxy, hydroxy-lower alkyl, carboxy, lower alkoxycarbonyl, hydroxyimino lower alkyl, amino, amino lower alkyl, mono- or di-lower alkylamino, mono- or di-lower alkylamino-lower alkyl, lower alkanoylamino, aminocarbonyl, lower alkylaminocarbonyl, lower dialkylaminocarbonyl, trifluoroacetylamino, trifluoromethyl, hydroxy, pyridyl, or on adjacent carbons can be ##STR3## wherein R' is hydrogen, lower alkanoyl, trifluoroacetyl and R" hydrogen or lower alkyl, R.sub.7 is a heteroaromatic radical or an aromatic radical selected from phenyl, naphthyl or phenanthryl, which aromatic radical may optionally be substituted by one or more substituents selected from chlorine, fluorine, lower alkyl, lower alkoxy, phenyl-lower alkoxy of 2-7 carbon atoms, lower alkanoyl, lower alkanoyloxy, hydroxy-lower alkyl, carboxy, lower alkoxycarbonyl, amino, amino-lower alkyl, mono- or di-lower alkylamino, mono- or di-lower alkylamino-lower alkyl, lower alkanoylamino, aminocarbonyl, lower alkylaminocarbonyl, lower dialkylaminocarbonyl, trifluoroacetylamino, trifluoromethyl, hydroxy or pyridyl, or on adjacent carbons can be ##STR4## wherein R' is hydrogen, lower alkanoyl, trifluoroacetyl and R" hydrogen or lower alkyl, R.sub.8, R.sub.9, R.sub.10, independently, are hydrogen, hydroxy, lower alkyl, lower alkoxy, hydroxy lower alkyl, fluorine, chlorine or lower alkanoyl provided that no more than one of R.sub.8, R.sub.9, and R.sub.10 is hydroxy, lower alkoxy, lower hydroxyalkyl, fluorine, chlorine or lower alkanoyl, and Y is CH or N, and their enantiomer and salts thereof are described. The compounds of formula I exhibit activity as inhibitors of 5-lipoxygenase and inhibit lipid peroxidation. They are, therefore, useful in the treatment of diseases caused or aggravated by excess oxidative metabolism of arachidonic acid via the 5-lipoxygenase pathway and in the treatment of inflammation, arthritis, allergies, asthma and psoriasis. The compounds of formula I can also be used to prevent peroxidation of lipids and thus protect lipid membranes from oxidative stress.

  公式为##STR1##的消旋化合物。其中A为--C.tbd.C--R.sub.6，--CH.sub.2 --CH.sub.2 --R.sub.7或##STR2##，R.sub.1为氢或较低的烷酰基，R.sub.2、R.sub.3和R.sub.4独立地为氢或较低的烷基，R.sub.5为较低的烷基，R.sub.6为异芳基或苯基，萘基或苯并芘基中选择的芳基，该芳基可以选择性地被氯、氟、较低烷基、较低烷氧基、苯基较低烷氧基、较低烷酰基、较低烷酰氧基、羟基较低烷基、羧基、较低烷氧羰基、羟基亚胺较低烷基、氨基、氨基较低烷基、单烷基氨基或二烷基氨基、单烷基氨基或二烷基氨基较低烷基、较低烷酰胺基、氨基羰基、较低烷基氨基羰基、较低二烷基氨基羰基、三氟乙酰氨基、三氟甲基、羟基、吡啶基或相邻碳上的可以是##STR3##，其中R'为氢、较低烷酰基、三氟乙酰基，R"为氢或较低烷基，R.sub.7为异芳基或苯基，选择自苯基、萘基或苯并芘基的芳基，该芳基可以选择性地被氯、氟、较低烷基、较低烷氧基、苯基较低烷氧基（碳原子数为2-7）、较低烷酰基、较低烷酰氧基、羟基较低烷基、羧基、较低烷氧羰基、氨基、氨基较低烷基、单烷基氨基或二烷基氨基、单烷基氨基或二烷基氨基较低烷基、较低烷酰胺基、氨基羰基、较低烷基氨基羰基、较低二烷基氨基羰基、三氟乙酰氨基、三氟甲基、羟基或吡啶基，或相邻碳上的可以是##STR4##，其中R'为氢、较低烷酰基、三氟乙酰基，R"为氢或较低烷基，R.sub.8、R.sub.9、R.sub.10独立地为氢、羟基、较低烷基、较低烷氧基、羟基较低烷基、氟、氯或较低烷酰基，但R.sub.8、R.sub.9和R.sub.10中不超过一个为羟基、较低烷氧基、较低羟基烷基、氟、氯或较低烷酰基，Y为CH或N，描述了它们的对映体和盐。公式I的化合物表现出作为5-脂氧酶抑制剂的活性，并抑制脂质过氧化。因此，它们在治疗由于花生四烯酸通过5-脂氧酶途径的过度氧化代谢引起或加重的疾病以及治疗炎症、关节炎、过敏、哮喘和牛皮癣方面是有用的。公式I的化合物还可用于预防脂质过氧化，从而保护脂质膜免受氧化应激的影响。
• Palladium-Catalyzed Tandem Heck-Lactonization from <i>o</i>-Iodophenols and Enoates: Synthesis of Coumarins and the Study of the Mechanism by Electrospray Ionization Mass Spectrometry
  作者：Talita de A. Fernandes、Boniek Gontijo Vaz、Marcos N. Eberlin、Alcides J. M. da Silva、Paulo R. R. Costa

  DOI：10.1021/jo1010922

  日期：2010.11.5

  and B). Using electrospray ionization for transferring ions directly from solution to the gas phase, and mass spectrometry for structural assignments, key cationic palladium intermediates have been successfully intercepted and structurally characterized for the first time for this type of reaction.

  在亚化学计量的Pd（p）存在下，研究了烯酸酯Z - 1a，b，E - 1a，E - 2a - d，Z -2e，2f和邻碘酚（4a - f）之间的串联Heck内酯化反应。OAc）2或PdCl 2，在有利于阳离子机理的实验条件下（条件A，B和C），生成香豆素5a - f和6a - e。在水性条件下（条件A和B）获得中等至极好的收率。使用电喷雾电离将离子直接从溶液转移到气相，并通过质谱进行结构分配，对于这种类型的反应，关键的阳离子钯中间体已成功被成功拦截并对其结构进行了首次表征。
• COMPOUND, RESIN, RESIST COMPOSITION AND METHOD FOR PRODUCING RESIST PATTERN
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：US20210389669A1

  公开（公告）日：2021-12-16

  Disclosed are a compound represented by formula (I), a resin and a resist composition: wherein R 1 represents an alkyl group having 1 to 6 carbon atoms which may have a halogen, hydrogen or halogen atom, R 2 and R 3 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms, R 4 represents a fluorine atom, an alkyl fluoride group having 1 to 6 carbon atoms or an alkyl group having 1 to 12 carbon atoms, and —CH 2 — included in the alkyl fluoride group and the alkyl group may be replaced by —O— or —CO—, R 5 represents a hydrogen atom, an alkylcarbonyl group having 2 to 6 carbon atoms or an acid-labile group, m2 represents an integer of 1 to 4, m4 represents an integer of 0 to 3, and m5 represents 1 or 2, in which 2≤m2+m4+m5≤5.

  揭示了一种由公式（I）表示的化合物，树脂和抗蚀组合物： 其中R1代表具有1至6个碳原子的烷基基团，其可以具有卤素，氢或卤素原子，R2和R3各自独立地表示氢原子或具有1至12个碳原子的碳氢基团，R4表示氟原子，具有1至6个碳原子的烷基氟化物基团或具有1至12个碳原子的烷基基团，且包括在烷基氟化物基团和烷基基团中的-CH2-可以被- O-或-CO-所取代，R5表示氢原子，具有2至6个碳原子的烷基羰基基团或酸敏感基团，m2表示1至4的整数，m4表示0至3的整数，m5表示1或2，在其中2≤m2+m4+m5≤5。
• Pharmacologically active chromanes
  申请人：Hoffmann-La Roche Inc.

  公开号：US05132310A1

  公开（公告）日：1992-07-21

  Racemic Compounds of the formula ##STR1## A is --C.tbd.C--R.sub.6, --CH.sub.2 --CH.sub.2 --R.sub.7 or ##STR2## R.sub.1 is hydrogen or lower alkanoyl, R.sub.2, R.sub.3, and R.sub.4 independently are hydrogen or lower alkyl, R.sub.5 is lower alkyl, R.sub.6 is a heteroaromatic radical or an aromatic radical selected from phenyl, naphthyl or phenanthryl, which aromatic radical may optionally be substituted by one or more substituents selected from chlorine, fluorine, lower alkyl, lower alkoxy, phenyl lower alkoxy, lower alkanoyl, lower alkanoyloxy, hydroxy-lower alkyl, carboxy, lower alkoxycarbonyl, hydroxyimino lower alkyl, amino, amino lower alkyl, mono- or di-lower alkylamino, mono- or di-lower alkylamino-lower alkyl, lower alkanoylamino, aminocarbonyl, lower alkylaminocarbonyl, lower dialkylaminocarbonyl, trifluoroacetylamino, trifluoromethyl, hydroxy, pyridyl, or on adjacent carbons can be ##STR3## wherein R' is hydrogen, lower alkanoyl, trifluoroacetyl and R" hydrogen or lower alkyl, R.sub.7 is a heteroaromatic radical or an aromatic radical selected from phenyl, naphthyl or phenanthryl, which aromatic radical may optionally be substituted by one or more substituents selected from chlorine, fluorine, lower alkyl, lower alkoxy, phenyl-lower alkoxy of 2-7 carbon atoms, lower alkanoyl, lower alkanoyloxy, hydroxy-lower alkyl, carboxy, lower alkoxycarbonyl, amino, amino-lower alkyl, mono- or di-lower alkylamino, mono- or di-lower alkylamino-lower alkyl, lower alkanoylamino, aminocarbonyl, lower alkylaminocarbonyl, lower dialkylaminocarbonyl, trifluoroacetylamino, trifluoromethyl, hydroxy or pyridyl, or on adjacent carbons can be ##STR4## wherein R' is hydrogen, lower alkanoyl, trifluoroacetyl and R" hydrogen or lower alkyl, R.sub.8, R.sub.9, and R.sub.10, independently, are hydrogen, hydroxy, lower alkyl, lower alkoxy, hydroxy lower alkyl, fluorine, chlorine or lower alkanoyl provided that no more than one of R.sub.8, R.sub.9, and R.sub.10 is hydroxy, lower alkoxy, lower hydroxyalkyl, fluorine, chlorine or lower alkanoyl, and Y is CH or N, and their enantiomer and salts thereof are described. The compounds of formula I exhibit activity as inhibitors of 5-lipoxygenase and inhibit lipid peroxidation. They are, therefore, useful in the treatment of diseases caused or aggravated by excess oxidative metabolism of arachidonic acid via the 5-lipoxygenase pathway and in the treatment of inflammation, arthritis, allergies, asthma and psoriasis. The compounds of formula I can also be used to prevent peroxidation of lipids and thus protect lipid membranes from oxidative stress.

  式为##STR1##的外消旋化合物，其中A为--C.tbd.C--R.sub.6，--CH.sub.2--CH.sub.2--R.sub.7或##STR2##R.sub.1为氢或低烷酰基，R.sub.2、R.sub.3和R.sub.4独立地为氢或低烷基，R.sub.5为低烷基，R.sub.6为杂环芳基或苯基、萘基或菲基中选择的芳基，该芳基可以选择地由一个或多个取代基选自氯、氟、低烷基、低烷氧基、苯基低烷氧基、低烷酰基、低烷酰氧基、羟基-低烷基、羧基、低烷氧羰基、羟基亚胺-低烷基、氨基、氨基低烷基、单或二低烷基氨基、单或二低烷基氨基-低烷基、低烷酰氨基、氨基羰基、低烷基氨基羰基、低二烷基氨基羰基、三氟乙酰氨基、三氟甲基、羟基、吡啶基或相邻碳上可以为##STR3##，其中R'为氢、低烷酰基、三氟乙酰基，R"为氢或低烷基，R.sub.7为杂环芳基或苯基、萘基或菲基中选择的芳基，该芳基可以选择地由一个或多个取代基选自氯、氟、低烷基、低烷氧基、2-7个碳原子的苯基-低烷氧基、低烷酰基、低烷酰氧基、羟基-低烷基、羧基、低烷氧羰基、氨基、氨基低烷基、单或二低烷基氨基、单或二低烷基氨基-低烷基、低烷酰氨基、氨基羰基、低烷基氨基羰基、低二烷基氨基羰基、三氟乙酰氨基、三氟甲基、羟基或吡啶基，或相邻碳上可以为##STR4##，其中R'为氢、低烷酰基、三氟乙酰基，R"为氢或低烷基，R.sub.8、R.sub.9和R.sub.10独立地为氢、羟基、低烷基、低烷氧基、羟基低烷基、氟、氯或低烷酰基，前提是R.sub.8、R.sub.9和R.sub.10中最多只有一个为羟基、低烷氧基、低羟基烷基、氟、氯或低烷酰基，Y为CH或N，它们的对映体和盐被描述。公式I的化合物表现为5-脂氧合酶的抑制剂和抑制脂质过氧化。因此，它们在治疗由过量的通过5-脂氧合酶途径的花生四烯酸氧化代谢引起或加重的疾病以及治疗炎症、关节炎、过敏、哮喘和牛皮癣方面是有用的。公式I的化合物也可以用于预防脂质过氧化，从而保护脂质膜免受氧化应激的影响。
• Pd-NHC Catalyzed Cyclopentannulation of Diazabicyclic Alkenes with <i>ortho</i>-aryl halides
  作者：B. A. Bhanu Prasad、Alexander E. Buechele、Scott R. Gilbertson

  DOI：10.1021/ol102270r

  日期：2010.12.3

  Pd-NHC catalyzed cyclopentannulat on of diazabicyclic alkenes with ortho- functionalized aryl halides is described. In all the reactions, a single diastereomer of the cyclopentannulated product is observed, and this reaction is very efficient under microwave irradiation.