2-chloro-1,4-dimethoxy-naphthalene | 73661-21-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-chloro-1,4-dimethoxy-naphthalene
• 英文别名: 2-Chlor-1,4-dimethoxy-naphthalin；2-Chloro-1,4-dimethoxynaphthalene
• CAS: 73661-21-9
• 化学式: C₁₂H₁₁ClO₂
• 分子量: 222.671
• InChiKey: OCZQPUBZNMBEHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-chloro-1,4-dimethoxy-naphthalene 在 三甲基氯硅烷 、 碘苯二乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 2,3-dichloro-1,4-dimethoxy-naphthalene
  参考文献：
  名称：

  Hypervalent Iodine Chemistry:  Mechanistic Investigation of the Novel Haloacetoxylation, Halogenation, and Acetoxylation Reactions of 1,4-Dimethoxynaphthalenes

  摘要：

  Treatment of 1,4-dimethoxynaphthalenes with iodosobenzene diacetate and trimethylsilyl chloride or bromide furnished the haloacetoxylated, acetoxylated, and halogenated 1,4-dimethoxynaphthalenes in excellent yield. The reaction pathway for each transformation was shown to be a function of reagent stoichiometry. A mechanistic hypothesis is presented that rationalizes the reaction pathways and explains the subtle differences in the halogenation reactions. The acetoxylation, for example, is thought to involve the formation of an iodonium ion that promotes the nucleophilic addition of acetate ion and subsequent 1,2-acetyl migration. Bromination occurs as a direct result of the oxidation of trimethylsilyl bromide to bromine, followed by electrophilic aromatic substitution. Chlorination is thought to proceed via a radical process and not the formation of molecular chlorine from the dissociation of iodosobenzene dichloride. The haloacetoxylation reaction also appears to be fairly specific for 1,4-dimethoxynaphthalenes, since the analogous reaction with a 1,4-dimethoxybenzene derivative was unsuccessful.

  DOI：

  10.1021/jo970525i
• 作为产物：
  描述：

  1,4-二甲氧基萘 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 三甲基氯硅烷 、 碘苯二乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以98%的产率得到2-chloro-1,4-dimethoxy-naphthalene
  参考文献：
  名称：

  Hypervalent Iodine Chemistry:  Mechanistic Investigation of the Novel Haloacetoxylation, Halogenation, and Acetoxylation Reactions of 1,4-Dimethoxynaphthalenes

  摘要：

  Treatment of 1,4-dimethoxynaphthalenes with iodosobenzene diacetate and trimethylsilyl chloride or bromide furnished the haloacetoxylated, acetoxylated, and halogenated 1,4-dimethoxynaphthalenes in excellent yield. The reaction pathway for each transformation was shown to be a function of reagent stoichiometry. A mechanistic hypothesis is presented that rationalizes the reaction pathways and explains the subtle differences in the halogenation reactions. The acetoxylation, for example, is thought to involve the formation of an iodonium ion that promotes the nucleophilic addition of acetate ion and subsequent 1,2-acetyl migration. Bromination occurs as a direct result of the oxidation of trimethylsilyl bromide to bromine, followed by electrophilic aromatic substitution. Chlorination is thought to proceed via a radical process and not the formation of molecular chlorine from the dissociation of iodosobenzene dichloride. The haloacetoxylation reaction also appears to be fairly specific for 1,4-dimethoxynaphthalenes, since the analogous reaction with a 1,4-dimethoxybenzene derivative was unsuccessful.

  DOI：

  10.1021/jo970525i

文献信息

• Bell, Kevin H., Australian Journal of Chemistry, 1985, vol. 38, # 8, p. 1209 - 1221
  作者：Bell, Kevin H.

  DOI：——

  日期：——
• Novel haloacetoxylation of 1,4-dimethoxynaphthalenes using hypervalent iodine chemistry
  作者：P.Andrew Evans、Thomas A. Brandt

  DOI：10.1016/0040-4039(96)01427-x

  日期：1996.9

  Treatment of 1,4-dimethoxynaphthalenes with iodosobenzene and trimethylsilyl chloride or bromide furnished the corresponding 2,3-haloacetoxylated-1,4-dimethoxynaphthalenes. Copyright (C) 1996 Elsevier Science Ltd
• Laatsch, Hartmut, Liebigs Annalen der Chemie, 1980, # 1, p. 140 - 157
  作者：Laatsch, Hartmut

  DOI：——

  日期：——
• Inoue et al., Yuki Gosei Kagaku Kyokaishi, 1956, vol. 14, p. 622,624
  作者：Inoue et al.

  DOI：——

  日期：——
• LAATSCH H., LIEBIGS ANN. CHEM., 1980, NO 1, 140-157
  作者：LAATSCH H.

  DOI：——

  日期：——