4-Methoxy-3-methyl-1-naphthol | 17789-52-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-Methoxy-3-methyl-1-naphthol
• 英文别名: 4-methoxy-3-methylnaphthalen-1-ol
• CAS: 17789-52-5
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: SHFLHAOXNPRMHU-UHFFFAOYSA-N

物化性质

• 沸点：
  358.1±22.0 °C(Predicted)
• 密度：
  1.160±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-Methoxy-3-methyl-1-naphthol 在 sodium hydroxide 、 potassium hexacyanoferrate(III) 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.25h， 生成 1,1',4,4'-Tetramethoxy-3,3'-dimethyl-2,2'-binaphthyl
  参考文献：
  名称：

  二聚萘醌，VI与重氮甲烷进行C-甲基化合成3,3'-比安帕鲁巴金及其相关3,3'-二甲基-2,2'-bi-1,4-萘醌

  摘要：

  6/7类型的3,3'-Dimethyl-2,2'-bi-1,4-萘醌不是或仅不是或仅不是通过苯酚/醌加成或通过3-甲基-1-苯酚的苯酚氧化而形成的萘酚的收率不理想。通过将重氮甲烷添加到3,3'-未取代的2,2'-联萘醌4/5中并将9a，9a'-Bi（3a，9a-dihydro- 3H-苯并[f]吲唑-4，9-醌）16。描述了二聚体6 / 7a - e的合成和性质。

  DOI：

  10.1002/jlac.198319830215
• 作为产物：
  描述：

  甲萘醌 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 正丁基锂 、 正己烷 、 氢气 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醚 为溶剂， 反应 0.28h， 生成 4-Methoxy-3-methyl-1-naphthol
  参考文献：
  名称：

  Laatsch, Hartmut, Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1985, vol. 40, # 4, p. 534 - 542

  摘要：

  DOI：

文献信息

• A facile synthesis of naturally occurring binaphthoquinones: efficient oxidative dimerization of 4-alkoxy-1-naphthols using silver(II) oxide–40% nitric acid
  作者：Yasuhiro Tanoue、Kazunori Sakata、Mamoru Hashimoto、Shin-ich Morishita、Moritsugu Hamada、Norihisa Kai、Takeshi Nagai

  DOI：10.1016/s0040-4020(01)01130-9

  日期：2002.1

  Oxidation of 4-alkoxy-1-naphthols with AgO–40% HNO3 occurred along with a dimerization to give the corresponding bi-1,4-naphthoquinones. The oxidative dimerization required one hydroxyl group and took place at its ortho position. This reaction was applicable to syntheses of naturally occurring binaphthoquinones, bivitamin K3 and 3,3′-bijuglone.

  用AgO–40％HNO 3氧化4-烷氧基-1-萘并进行二聚反应得到相应的bi-1,4-萘醌。氧化二聚反应需要一个羟基并发生在其邻位。该反应适用于天然存在的联萘醌，联维生素K 3和3,3'-联juglone的合成。
• Process for making 3-prenylated menaquinones and ether intermediates
  申请人：The Regents of the University of California

  公开号：US03948958A1

  公开（公告）日：1976-04-06

  3-Prenyl-substituted-2-alkyl menaquinones are made by reacting an alkali metal salt of a 3-alkyl-4-alkoxy or aralkoxy-1-naphthol with a prenyl halide, and oxidizing the resulting 2-prenyl-3-alkyl-4-alkoxy or aralkoxy-1-naphthol to the corresponding 3-prenyl-substituted-2-alkyl menaquinone. There is also disclosed a procedure for making the alkali metal salts involving the preparation of an ether-ester and hydrogenolysis.

  3-前醇基取代的2-烷基维生素K2是通过将3-烷基-4-烷氧基或芳基烷氧基-1-萘酚的碱金属盐与前醇卤代物反应，并将生成的2-前醇基-3-烷基-4-烷氧基或芳基烷氧基-1-萘酚氧化成相应的3-前醇基取代的2-烷基维生素K2来制备的。还公开了一种制备碱金属盐的方法，涉及醚酯的制备和氢解反应。
• Process for preparing 3-alkyl-4-alkoxy-1-naphthols
  申请人：The Regents of the University of California

  公开号：US04060558A1

  公开（公告）日：1977-11-29

  3-Prenyl-substituted-2-alkyl menaquinones are made by reacting an alkali metal salt of a 3-alkyl-4-alkoxy or aralkoxy-1-naphthol with a prenyl halide, and oxidizing the resulting 2-prenyl-3-alkyl-4-alkoxy or aralkoxy-1-naphthol to the corresponding 3-prenyl-substituted-2-alkyl menaquinone. There is also disclosed a procedure for making the alkali metal salts involving the preparation of an ether-ester and hydrogenolysis.

  通过将3-烷基-4-烷氧基或芳基烷氧基-1-萘酚的碱金属盐与异戊烯卤代物反应，并将所得的2-异戊烯基-3-烷基-4-烷氧基或芳基烷氧基-1-萘酚氧化为相应的3-异戊烯基取代的2-烷基维生素K。还公开了一种制备醚酯和氢解制备碱金属盐的方法。
• Quinone derivatives
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04559177A1

  公开（公告）日：1985-12-17

  A compound of the formula: ##STR1## wherein m is an integer of 11 to 22; R.sub.1 is alkyl having 1 to 4 carbon atoms; R.sub.2 is hydrogen, alkyl having 1 to 4 carbon atoms or carboxylic acyl having 1 to 8 carbon atoms. Such compounds have pharmaceutical activities such as hypotensive, tissue metabolism stimulating, immuno-regulatory and lysosomal membrane stabilizing activity, and inhibit SRS-A production, and are useful as a heart failure remedy, cerebral circulation disturbance remedy, immuno-regulator, and antiallergic drug.

  一种化合物的化学式：##STR1## 其中m是11至22的整数；R.sub.1是具有1至4个碳原子的烷基；R.sub.2是氢，具有1至4个碳原子的烷基或具有1至8个碳原子的羧酸酰基。这些化合物具有药理活性，如降压、组织代谢刺激、免疫调节和溶酶体膜稳定活性，并抑制SRS-A的产生，可用作心力衰竭治疗、脑循环障碍治疗、免疫调节剂和抗过敏药物。
• 2,3-Dialkoxy-1,4-quinone derivatives; method of producing 1,4-quinone derivatives
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0021841A2

  公开（公告）日：1981-01-07

  A compound of the general formula: wherein m is an integer of 10 to 21; R1 is lower alkyl having 1 to 4 carbon atoms; B is a -CH2- or-CO- group, when B is-CH2-, R2 is hydrogen, lower alkyl having 1 to 4 carbon atoms or lower acyl having 1 to 8 carbon atoms, and when B is -CO-, R2 is hydrogen or lower alkyl having 1 to 4 carbon atoms, has pharmaceutical activities such as hypotensive, tissue metabolism stimulating, immunoregulatory, lysosomal membrane stablizing and SRS-A production inhibitory activities and is useful as a heart failure remedy, cerebral circulation disturbance remedy, immunoregulatorand antiallergic drug. A compound of the general formula: [wherein each R3 is lower alkyl having 1 to 4 carbon atoms or lower alkoxy having 1 to 4 carbon atoms, or two R3's taken together represent -CH =CH-CH =CH-; n is O or an integer of 1 to 20 and when n is 1 to 20, A is -CH2-, or -CO- and Z is CH2OH, acyloxymethyl having 2 to 11 carbon atoms, esterified or unesterified carboxyl having 1 to 5 carbon atoms, lower alkoxymethyl having 2 to 5 carbon atoms, silyloxymethyl having 4 to 7 carbon atoms or acetalmethyl having 3 to 8 carbon atoms; when n is O, -A(CH2)n-Z is (wherein - is 0 or an integer of 1 to 12) and Z is H] can be produced with advantage for commercial-scale production by oxidising a compound of the general formula: [wherein X1 or X2 is hydroxyl or amino, with the other being H or an esterified hydroxyl group having 1 to 8 carbon atoms or etherified hydroxyl group having 2 to to 8 carbon atoms; the other symbols are as defined above] with oxygen or air in the presence of a transition metal complex compound.

  通式如下的化合物 其中 m 是 10 至 21 的整数；R1 是具有 1 至 4 个碳原子的低级烷基；当 B 为-CH2-时，R2 为氢、具有 1 至 4 个碳原子的低级烷基或具有 1 至 8 个碳原子的低级酰基；当 B 为-CO-时，R2 为氢或具有 1 至 4 个碳原子的低级烷基、具有降血压、促进组织代谢、免疫调节、稳定溶酶体膜和抑制 SRS-A 生成等药物活性，可用作治疗心力衰竭、脑循环障碍、免疫调节和抗过敏药物。通式如下的化合物 [其中每个 R3 是具有 1 至 4 个碳原子的低级烷基或具有 1 至 4 个碳原子的低级烷氧基，或两个 R3 共同代表-CH =CH-CH =CH-；n 是 O 或 1 至 20 的整数，当 n 为 1 至 20 时，A 是-CH2-、 或-CO-，Z 是 CH2OH、具有 2 至 11 个碳原子的酰氧基甲基、具有 1 至 5 个碳原子的酯化或未酯化羧基、具有 2 至 5 个碳原子的低级烷氧基甲基、具有 4 至 7 个碳原子的硅氧基甲基或具有 3 至 8 个碳原子的乙缩醛甲基；当 n 是 O 时，-A(CH2)n-Z 是 (其中 - 为 0 或 1 至 12 的整数），Z 为 H]，可通过氧化通式如下的化合物生产，具有商业规模生产的优势： [其中 X1 或 X2 为羟基或氨基，另一个为 H 或具有 1 至 8 个碳原子的酯化羟基或具有 2 至 8 个碳原子的醚化羟基；其他符号如上定义]，在过渡金属复合物存在下，与氧气或空气氧化。