4-氯-3-甲基邻苯二酚 | 18257-21-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 4-氯-3-甲基邻苯二酚
• 英文名称: 4-chloro-1,2-dihydroxy-3-methylbenzene
• 英文别名: 3-methyl-4-chloropyrocatechol；4-Chloro-3-methylpyrocatechol；4-chloro-3-methylbenzene-1,2-diol
• CAS: 18257-21-1
• 化学式: C₇H₇ClO₂
• 分子量: 158.584
• InChiKey: IRYAHOGVOVVMOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,2,2,5-tetrachloro-4-methylbenzo[d]-1,3,2-dioxaphosphole 在 盐酸 作用下， 以 水 为溶剂， 以38%的产率得到4-氯-3-甲基邻苯二酚
  参考文献：
  名称：

  Chlorinations of derivatives of 2,2,2-trichlorobenzo-1,3,2-dioxaphospholes

  摘要：

  By P-31, C-13, C-13-{H-1}, and H-1 NMR spectroscopy the chlorination of 4- and 5-methyl-2,2,2-trichlorobenzo-1,3,2-dioxaphosphols was shown to provide in quantitative yield 4-methyl-2,2,2,5-tetrachloro- and 6-methyl-2,2,2,5-tetrachlorobenzo-1,3,2-dioxaphosphols. Their hydrolysis led to the formation of difficultly available 4-methyl-5-chloro- and 3-methyl-4-chloro-1,2-dihydroxybenzenes. The structure of the latter compound was established by XRD analysis. The 5-methyl-2-chlorobenzo-1,3,2-dioxaphosphol treated with excess chlorine was converted in succession into 5-methyl-2,3,4,5,6,6-hexachlorocyclohex-1-en-3-yl dichlorophosphate and 5-methyl-1,2,4,4,5,6-hexachlorocyclohex-1-en-3-yl dichlorophosphate. The hydrolysis resulted in 5-methyl-2,3,4,5,6,6-hexachlorocyclohex-2-en-1-yl dihydrophosphate. The configuration of three chiral carbon atoms in the latter was established by XRD study. In the course of the chlorination the aromaticity of the ortho-phenylene fragment was distorted and 3,3-sigmatropic shift of the dichlorophosphoryl group occurred. The reaction with chlorine of 5-tert-butyl-2,2,2-trichlorobenzo-1,3,2-dioxaphosphol and 2,2,2-trichloro-benzo-1,3,2-dioxaphosphol was not selective: The reaction product obtained in excess chlorine transformed on hydrolysis into tetrachloropyrocatechol. Its solvates with water and dioxane were studies by XRD analysis.

  DOI：

  10.1134/s1070428008070087

文献信息

• Molecular Characterization and Substrate Specificity of Nitrobenzene Dioxygenase from <i>Comamonas</i> sp. Strain JS765
  作者：Daniel J. Lessner、Glenn R. Johnson、Rebecca E. Parales、Jim C. Spain、David T. Gibson

  DOI：10.1128/aem.68.2.634-641.2002

  日期：2002.2

  Comamonas sp. strain JS765 can grow with nitrobenzene as the sole source of carbon, nitrogen, and energy. We report here the sequence of the genes encoding nitrobenzene dioxygenase (NBDO), which catalyzes the first step in the degradation of nitrobenzene by strain JS765. The components of NBDO were designated Reductase _NBZ , Ferredoxin _NBZ , Oxygenase _NBZα , and Oxygenase _NBZβ , with the gene designations nbzAa , nbzAb , nbzAc , and nbzAd , respectively. Sequence analysis showed that the components of NBDO have a high level of homology with the naphthalene family of Rieske nonheme iron oxygenases, in particular, 2-nitrotoluene dioxygenase from Pseudomonas sp. strain JS42. The enzyme oxidizes a wide range of substrates, and relative reaction rates with partially purified Oxygenase _NBZ revealed a preference for 3-nitrotoluene, which was shown to be a growth substrate for JS765. NBDO is the first member of the naphthalene family of Rieske nonheme iron oxygenases reported to oxidize all of the isomers of mono- and dinitrotoluenes with the concomitant release of nitrite.

  摘要 Comamonas 菌株 JS765 能以硝基苯作为唯一的碳、氮和能量来源进行生长。我们在此报告了编码硝基苯二氧酶（NBDO）的基因序列，该酶催化了 JS765 菌株降解硝基苯的第一步。NBDO 的组分被命名为还原酶 NBZ 铁氧化还原酶 NBZ 氧化酶 NBZα 和氧化酶 NBZβ ，基因名称为 nbzAa , nbzAb , nbzAc 和 nbzAd 和 nbzAd。序列分析表明，NBDO 的组成成分与萘家族的里斯克非血红素铁氧合酶，特别是假单胞菌中的 2-硝基甲苯二氧合酶，具有高度的同源性。 假单胞菌 菌株 JS42 的 2-硝基甲苯二氧酶。该酶可氧化多种底物，与部分纯化的加氧酶的相对反应速率如下 NBZ 的相对反应速率显示，该酶偏好 3-硝基甲苯，而 3-硝基甲苯被证明是 JS765 的生长底物。据报道，NBDO 是萘系里斯克非血红素铁氧合酶家族的第一个成员，它能氧化一硝基甲苯和二硝基甲苯的所有异构体，同时释放亚硝酸盐。
• Regioselective chlorination of 4- and 5-methyl-2,2,2-trichlorobenzo[d]-1,3,2-dioxaphospholes
  作者：Elena N. Varaksina、Vladimir F. Mironov、Alfia A. Shtyrlina、Alexey B. Dobrynin、Igor A. Litvinov、Alexander I. Konovalov

  DOI：10.1070/mc2005v015n03abeh002069

  日期：2005.1

  The reactions of 4- and 5-methyl-2,2,2-trichlorobenzo[d]-1,3,2-dioxaphospholes with molecular chlorine in an 1:1 ratio occur selectively to give 4-methyl-2,2,2,5-tetrachloro- and 5-methyl-2,2,2,6-tetrachlorobenzo[d]-1,3,2-dioxaphospholes, which undergo hydrolysis to 4-chloro-3-methyl- and 4-chloro-5-methyl-1,2-dihydroxybenzenes, respectively.
• EP1995250A1
  申请人：——

  公开号：EP1995250A1

  公开（公告）日：2008-11-26
• Ligand, Method for Producing the Same, and Catalyst Using the Ligand
  申请人：Shibasaki Masakatsu

  公开号：US20090023579A1

  公开（公告）日：2009-01-22

  Disclosed is a novel asymmetric ligand which can be synthesized by a short process at low cost and is capable of exhibiting higher catalytic activity and enantioselectivity than the conventional ligands derived from sugars. Also disclosed are a method for producing such an asymmetric ligand, and a catalyst using such an asymmetric ligand. Specifically disclosed is a ligand represented by the general formula I below or the like. (In the formula, R 1 and R 2 independently represent 0-5 substituents; X represents P, As or N; m represents an integer of 0-7; n represents an integer of 0-3; A 1 -A 4 independently represent hydrogen, fluorine, chlorine, bromine, benzoyl or acetyl, or alternatively A 2 and A 3 combine together to form a ring.)
• US6759435B1
  申请人：——

  公开号：US6759435B1

  公开（公告）日：2004-07-06