3-ethyl-6-methoxy-2-naphthol | 88116-14-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-ethyl-6-methoxy-2-naphthol
• 英文别名: 3-Ethyl-6-methoxynaphthalen-2-ol
• CAS: 88116-14-7
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: NQTNRADITIBQAW-UHFFFAOYSA-N

物化性质

• 熔点：
  87 °C
• 沸点：
  353.3±22.0 °C(Predicted)
• 密度：
  1.131±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  3-ethyl-6-methoxy-2-naphthol 在 氧气 、 copper(l) chloride 作用下， 以 乙腈 为溶剂， 以61%的产率得到3-Ethyl-6-methoxynaphthalene-1,2-dione
  参考文献：
  名称：

  Annulation reactions leading to naphthalene derivatives. New syntheses of natural 1,2- and 1,4-naphthoquinones

  摘要：

  DOI：

  10.1021/jo00218a022
• 作为产物：
  描述：

  1-[(Benzenesulfonyl)methyl]-2-(bromomethyl)-4-methoxybenzene 生成 3-ethyl-6-methoxy-2-naphthol
  参考文献：
  名称：

  芳环的新环化方法。萘，蒽和菲结构的新合成。

  摘要：

  2-（苯磺酰基）甲基苄基溴及其衍生物与萘酸酯，1，3-酮酸酯和内酯的缩合导致萘衍生物和其他多环体系的区域选择性形成。

  DOI：

  10.1016/s0040-4039(00)86032-3

文献信息

• New annulation methods of aromatic rings. New syntheses of naphthalene, anthracene and phenanthrene structures.
  作者：Eugene Ghera、Yehoshua Ben-David

  DOI：10.1016/s0040-4039(00)86032-3

  日期：1983.1

  Condensation of 2-(phenylsulfonyl)methyl benzyl bromide and its derivatives with nalonates, 1,3-ketoesters and lactones resulted in the regioselective formation of naphthalene derivatives and of other polycyclic systems.

  2-（苯磺酰基）甲基苄基溴及其衍生物与萘酸酯，1，3-酮酸酯和内酯的缩合导致萘衍生物和其他多环体系的区域选择性形成。
• Novel photochemical reactions of 1- and 2-naphthols with ethylene promoted by aluminum halides
  作者：Kiyomi Kakiuchi、Bunji Yamaguchi、Masahiko Kinugawa、Masaki Ue、Yoshito Tobe、Yoshinobu Odaira

  DOI：10.1021/jo00062a024

  日期：1993.5

  Novel photoreactions of 1- and 2-naphthols with ethylene promoted by aluminum halides are described. Irradiation of 2-naphthol (2a) with AlX3 (X = Cl, Br) and ethylene in CH2Cl2 gave the corresponding [2 + 2] cycloadduct 7a in good yields. The major side product was 2-ethyl-1-naphthol (8a). Of the Lewis acids and alkenes examined, only AlCl3 and AlBr3 effected the reaction and only ethylene gave satisfactory results, although allene can also be employed. Naphthols 2b-e having different electron-attracting substituents on C-6 afforded [2 + 2] adducts 7b-e in moderate to good yields, while the reactions of C-3-alkyl-substituted derivatives 8a and 15b were unsuccessful. By contrast, 1-naphthol (1a) and its derivatives 1b-e exhibited diverse reactivities depending on the substituent on C-2, C-3, or C-6. Namely 1a and 3-methyl derivative 1b afforded [2 + 2] cycloadducts 16a and 16b in moderate yields. On the other hand, 2-methyl and 2-propyl derivatives 1c and 1d yielded unusual products like indenones 22a and 22b and cyclopropyl ketones 23a and 23b, respectively. 6-Methoxy derivative 1e also gave indenone 30. Plausible reaction mechanisms leading to the observed products are presented.
• Novel photocycloaddition of 2-naphthols to ethylene in the presence of Lewis acid
  作者：Masaki Ue、Masahiko Kinugawa、Kiyomi Kakiuchi、Yoshito Tobe、Yoshinobu Odaira

  DOI：10.1016/s0040-4039(01)93339-8

  日期：——
• UE, MASAKI;KINUGAWA, MASAHIKO;KAKIUCHI, KIYOMI;TOBE, YOSHITO;ODAIRA, YOSH+, TETRAHEDRON LETT., 30,(1989) N5, C. 6193-6194
  作者：UE, MASAKI、KINUGAWA, MASAHIKO、KAKIUCHI, KIYOMI、TOBE, YOSHITO、ODAIRA, YOSH+

  DOI：——

  日期：——
• CHERA, E.;BEN-DAVID, Y., TETRAHEDRON LETT., 1983, 24, N 33, 3533-3536
  作者：CHERA, E.、BEN-DAVID, Y.

  DOI：——

  日期：——