2-羟基-5-甲基-1,4-萘醌 | 63432-44-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-羟基-5-甲基-1,4-萘醌
• 英文名称: 2-hydroxy-5-methyl-1,4-naphthoquinone
• CAS: 63432-44-0
• 化学式: C₁₁H₈O₃
• 分子量: 188.183
• InChiKey: SUEGHCWUBGHHCF-UHFFFAOYSA-N

物化性质

• 熔点：
  145-146 °C
• 沸点：
  379.6±42.0 °C(Predicted)
• 密度：
  1.406±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.82
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-羟基-5-甲基-1,4-萘醌 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 生成 3,5-二甲基萘并[2,3-b]呋喃-4,9-二酮
  参考文献：
  名称：

  Photoinduced molecular transformations. Part 120. New one-step general synthesis of 2,3-dihydronaphtho[2,3-b]-furan-4,9-diones by regioselective photoaddition of 2-hydroxy-1,4-naphthoquinones with various alkenes and its application to a two-step synthesis of maturinone

  摘要：

  A one-step formation of 2,3-dihydronaphtho-[2,3-b]furan-4,9-diones in 41-83% by a new 2 + 3 type regioselective photoaddition of 2-hydroxy-1,4-naphthoquinones with a variety of alkenes is reported. The dihydronaphthofurandiones can readily be transformed into naphtho[2,3-b]furan-4,9-diones including a natural quinone, maurinone.

  DOI：

  10.1021/jo00010a003
• 作为产物：
  描述：

  1,4-dihydro-1,4-dioxo-5-methylnaphthalene 在 水 、 copper (I) acetate 、 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 2.0h， 生成 2-羟基-5-甲基-1,4-萘醌
  参考文献：
  名称：

  Synthesis and efficiency of photolysis of methylated 2-dialkylamino- and 2-piperidino-1,4-naphthoquinones

  摘要：

  2-Dialkylamino- and 2-piperidino-1,4-naphthoquinones with a methyl group in position 3 or 5(8) of the naphthoquinones were synthesized by reacting dimethyl- and diethylamines and piperidine with 2- and 5-methyl-1,4-naphthoquinones. The quantum yields of photoconversion of the synthesized compounds in benzene were determined. A 1.2- to 6.5-fold increase of the quantum yield over that of 2-dimethylamino-1,4-napthoquinone was established. A comparison of the quantum yields with the calculated charges on the reaction centers in the excited (T1) state showed that there is not a linear relationship between them.

  DOI：

  10.1007/bf00863084

文献信息

• Palladium(II)-Catalyzed Oxidative Annulation of 2-Hydroxynaphthalene-1,4-diones and Internal Alkynes via C–H Functionalization
  作者：Peng Sun、Jiaojiao Yang、Jinsong Peng、Baichuan Mo、Xin Chen、Xiang Li、Chunxia Chen

  DOI：10.1021/acs.joc.9b03153

  日期：2020.5.15

  An efficient Pd(II)-catalyzed oxidative annulation of 2-hydroxynaphthalene-1,4-diones and internal alkynes has been developed with high step efficiency. A broad range of functional groups are compatible with this reaction, thus providing a new entry to diverse naphtho[2,3-b]furan-4,9-dione derivatives in good to high yields.

  已经开发了一种高效的Pd（II）催化的2-羟基萘-1,4-二酮和内部炔烃的氧化环化反应，具有较高的步长效率。各种各样的官能团都可与该反应相容，从而以高至高收率提供了新的各种萘并[2,3-b]呋喃-4,9-二酮衍生物的入口。
• The chemistry of Quinones. I. Directive effects in the Substitution of Naphthoquinones
  作者：RG Cooke、H Dowd、W Segal

  DOI：10.1071/ch9530038

  日期：——

  The reaction of dimethylamine with 5-methoxy-1,4-naphthoquinone gives approximately equal amounts of the two possible substitution products and with 6-methyl-1,4-naphthoquinone followed by acid hydrolysis 2-hydroxy-6-methyl-l,4-naphtho-quinone is the principal product. Similar treatment of 5-methyl-1,4-naphthoquinone gives mostly 3-hydroxy-5-methyl-l,4-naphtlioquinone. The isomer, 2-hydroxy-5- methyl-1,4-naphthoquinone, has been prepared by another method. The product of Thiele-Winter addition of acetic anhydride to juglone is shown to be a mixture of the two possible isomers, but authentic 1,3,4,5-tetra-acetoxynaphthalene has been prepared from 3,5-dihydroxy-1,4-naphthoquinone. The reaction of acetic anhydride with plumbagin gives three compounds, the composition of the mixture depending on the time of contact. Juglone and plumbagin have been selectively brominated in the 6-position and certain other halogen derivatives of these quinones have been prepared. The preparation of 3-chloro-5-hydroxy-2-methyl-1,4-naphthoquinone provides a new route by which droserone may be obtained from plumbagin.

  二甲胺与 与 5-甲氧基-1,4-萘醌的反应会产生近似等量的两种可能的取代产物。 与 6-甲基-1,4-萘醌反应，然后进行酸水解，可生成 2-羟基-6-甲基-1,4-萘醌。 2-hydroxy-6-methyl-l,4-naphtho-quinone 是主要产物。 产物。对 5-甲基-1,4-萘醌进行类似处理后，主要产物为 3-羟基-5-甲基-l,4-萘醌。异构体 2-羟基-5-甲基-1,4-萘醌是主要产物。 甲基-1,4-萘醌的异构体。其产物为 乙酸酐与丁二酮的 Thiele-Winter 加成产物被证明是两种可能异构体的混合物。 但真正的 1，3，4，5-四乙酰氧基萘是由 3，5-二乙酰氧基萘制备的。 但真正的 1,3,4,5-四乙酰氧基萘是由 3,5-二羟基-1,4-萘醌制备的。乙酸酐与 反应生成三种化合物，混合物的成分取决于接触的时间。 取决于接触的时间。Juglone 和 plumbagin 在 6 位被选择性溴化。 6 位溴化，并制备出了这些醌类化合物的某些其他卤素衍生物。 醌的某些其他卤素衍生物。3-氯-5-羟基-2-甲基-1,4-萘醌的制备方法 提供了一条从 plumbagin 中获得 droserone 的新途径。
• Photoinduced molecular transformations. Part 120. New one-step general synthesis of 2,3-dihydronaphtho[2,3-b]-furan-4,9-diones by regioselective photoaddition of 2-hydroxy-1,4-naphthoquinones with various alkenes and its application to a two-step synthesis of maturinone
  作者：Kazuhiro Kobayashi、Hideki Shimizu、Akiyoshi Sasaki、Hiroshi Suginome

  DOI：10.1021/jo00010a003

  日期：1991.5

  A one-step formation of 2,3-dihydronaphtho-[2,3-b]furan-4,9-diones in 41-83% by a new 2 + 3 type regioselective photoaddition of 2-hydroxy-1,4-naphthoquinones with a variety of alkenes is reported. The dihydronaphthofurandiones can readily be transformed into naphtho[2,3-b]furan-4,9-diones including a natural quinone, maurinone.
• KOBAYASHI, KAZUHIRO;SHIMIZU, HIDEKI;SASAKI, AKIYOSHI;SUGINOME, HIROSHI, J. ORG. CHEM., 56,(1991) N, C. 3204-3205
  作者：KOBAYASHI, KAZUHIRO、SHIMIZU, HIDEKI、SASAKI, AKIYOSHI、SUGINOME, HIROSHI

  DOI：——

  日期：——
• RADICAL POLYMERIZATION CONTROL AGENT AND RADICAL POLYMERIZATION CONTROL METHOD
  申请人：Kawasaki Kasei Chemicals Ltd.

  公开号：US20210122692A1

  公开（公告）日：2021-04-29

  A conventional polymerization inhibitor is for example an agent to scavenge radicals generated during storage of a radical polymerizable compound and used to stably handle the radical polymerizable compound, but is unnecessary when the radical polymerizable compound is to be subjected to radical polymerization reaction, and is preferably removed at the time of the radical polymerization reaction. The object of the present invention is to obviate inconvenience of removing the polymerization inhibitor at the time of radical polymerization. The radical polymerization control agent contained in a radical polymerizable composition of the present invention functions as a radical polymerization inhibitor for example stored in a dark place, but loses its radical polymerization inhibiting effect when polymerization is initiated while being irradiated with light at a certain specific wavelength at the time of polymerization. Thus, radical polymerization of the radical polymerizable compound is easily initiated without increasing the amount of a radical polymerization initiator. That is, the radical polymerization control agent of the present invention is a radical polymerization control agent which is a corn pound having an effect to inhibit radical polymerization of a radical polymerizable compound and which loses the radical polymerization inhibiting effect under irradiation with light rays containing light within a wavelength range of from 300 nm to 500 nm.