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1-溴-4-甲氧基-2,3,5,6-四甲基-苯 | 56474-57-8

中文名称
1-溴-4-甲氧基-2,3,5,6-四甲基-苯
中文别名
——
英文名称
4-Bromo-2,3,5,6-tetramethylanisole
英文别名
Bromdurenol-methylether;4-Brom-2.3.5.6-tetramethylanisol;1-Bromo-4-methoxy-2,3,5,6-tetramethylbenzene
1-溴-4-甲氧基-2,3,5,6-四甲基-苯化学式
CAS
56474-57-8
化学式
C11H15BrO
mdl
——
分子量
243.143
InChiKey
CALWRWLFQOSHNJ-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    4
  • 重原子数:
    13
  • 可旋转键数:
    1
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.45
  • 拓扑面积:
    9.2
  • 氢给体数:
    0
  • 氢受体数:
    1

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    1-溴-4-甲氧基-2,3,5,6-四甲基-苯正丁基锂硼酸三异丙酯盐酸 作用下, 以 四氢呋喃环己烷 为溶剂, 反应 1.0h, 以55%的产率得到(4-methoxy-2,3,5,6-tetramethyl)-phenyl boronic acid
    参考文献:
    名称:
    Syntheses of extreme sterically hindered 4-methoxyboronic acids
    摘要:
    4-Iodoanisoles 3a,b, 3d and 4-bromoanisoles 4a-d were readily obtained. An extreme steric hindrance precluded obtaining 3c. Catalytic borylation of 3a,b, 3d followed by hydrolysis of boronic ester 26a,b, 26d easily provided the boronic acids 5a,b, 5d. Compounds Sa and 5d were also synthesised, starting from 4a and 4d, by halogen/metal exchange. Because of a too important steric hindrance, this last reaction failed with 4c and 4b led to the unexpected but stable boronic ester 6. The final obtaining of 5b required a strongly basic hydrolysis with heating. (C) 2009 Elsevier Ltd. All rights reserved.
    DOI:
    10.1016/j.tet.2009.11.103
  • 作为产物:
    描述:
    2,3,5,6-tetramethylanisoleN-溴代丁二酰亚胺(NBS) 作用下, 以 乙腈 为溶剂, 以98%的产率得到1-溴-4-甲氧基-2,3,5,6-四甲基-苯
    参考文献:
    名称:
    Syntheses of extreme sterically hindered 4-methoxyboronic acids
    摘要:
    4-Iodoanisoles 3a,b, 3d and 4-bromoanisoles 4a-d were readily obtained. An extreme steric hindrance precluded obtaining 3c. Catalytic borylation of 3a,b, 3d followed by hydrolysis of boronic ester 26a,b, 26d easily provided the boronic acids 5a,b, 5d. Compounds Sa and 5d were also synthesised, starting from 4a and 4d, by halogen/metal exchange. Because of a too important steric hindrance, this last reaction failed with 4c and 4b led to the unexpected but stable boronic ester 6. The final obtaining of 5b required a strongly basic hydrolysis with heating. (C) 2009 Elsevier Ltd. All rights reserved.
    DOI:
    10.1016/j.tet.2009.11.103
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文献信息

  • Nuclear versus Side-Chain Bromination of Methyl-Substituted Anisoles by N-Bromosuccinimide
    作者:Gert-Jan M. Gruter、Otto S. Akkerman、Friedrich Bickelhaupt
    DOI:10.1021/jo00095a023
    日期:1994.8
    The reactions of methyl-substituted anisoles with N-bromosuccinimide in CCl4 are reported. In the absence of a catalyst and under irradiation, some of these substrates undergo nuclear bromination in competition with the well-known side-chain bromination. With 2-methylanisole and with 2,6-dimethylanisole, nuclear bromination is not observed, whereas with 3,5-dimethylanisole, nuclear bromination at the 4-position is the dominating reaction. Investigation of the reactivity of several other methyl-substituted anisoles revealed the following general trend: methyl-substituted anisoles are attacked at the position para to the methoxy group rather than at the side chain when (at least) two methyl groups are present at positions 3 and 5. When positions 2 and 6 are both occupied, nuclear bromination is retarded; in 2,6-dimethylanisole and in 2,3,6-trimethylanisole, only side-chain bromination is observed. In contrast, in 2,3,5,6-tetramethylanisole, the 4-position is sufficiently reactive to be brominated, because the decrease in reactivity by the presence of two methyl groups at positions 2 and 6 is overruled by the two additional methyl groups at positions 3 and 5; as a result, both nuclear and side-chain bromination occur. The observed chemospecificity can be rationalized by a difference in mechanism: the side-chain bromination is a radical reaction, while the nuclear bromination is an electrophilic aromatic substitution reaction, which is so far contrary to expectation, as irradiation had been expected to favor radical processes.
  • Kamshii,L.P. et al., Journal of Organic Chemistry USSR (English Translation), 1977, vol. 13, p. 740 - 746
    作者:Kamshii,L.P. et al.
    DOI:——
    日期:——
  • Gruter Gert-Jan M., Akkerman Otto S., Bickelhaupt Friedrich, J. Org. Chem, 59 (1994) N 16, S 4473- 4481
    作者:Gruter Gert-Jan M., Akkerman Otto S., Bickelhaupt Friedrich
    DOI:——
    日期:——
  • US4025633A
    申请人:——
    公开号:US4025633A
    公开(公告)日:1977-05-24
  • US4361573A
    申请人:——
    公开号:US4361573A
    公开(公告)日:1982-11-30
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