2-(Bromomethyl)-1,3,4-trimethylbenzene | 54757-29-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(Bromomethyl)-1,3,4-trimethylbenzene
• 英文别名: bromomethyl-1 trimethyl-2,3,6 benzene；2,3,6-trimethyl-1-bromomethylbenzene；2,3,6-trimethylbenzyl bromide；2,3,6-trimethyl-benzyl bromide；2,3,6-Trimethyl-benzylbromid；2.3.6-Trimethyl-benzyl-bromid；Benzene, 2-(bromomethyl)-1,3,4-trimethyl-
• CAS: 54757-29-8
• 化学式: C₁₀H₁₃Br
• 分子量: 213.117
• InChiKey: VHJZQAMILFUIKW-UHFFFAOYSA-N

物化性质

• 熔点：
  20-24 °C
• 沸点：
  146 °C
• 密度：
  1.2951 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-(Bromomethyl)-1,3,4-trimethylbenzene 在 氢氧化钾 、 乙醇 作用下， 生成 (2,3,6-trimethyl-benzyl)-malonic acid
  参考文献：
  名称：

  The Addition of Ethyl Diazoacetate to Prehnitene¹

  摘要：

  DOI：

  10.1021/ja01270a044
• 作为产物：
  描述：

  四甲基萘 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 生成 2-(Bromomethyl)-1,3,4-trimethylbenzene
  参考文献：
  名称：

  碳的均质置换：X.甲苯磺酰碘作为甲苯磺酰基自由基的来源，用于形成烯丙基，苄基，环丙基羰基，螺环丙基环烷基，双环[1.0.3]烷基和双环[1.0.4]烷基-4 -有机钴肟的甲苯磺酸酯

  摘要：

  4-甲苯磺酰碘在约40°C下与多种烯基和苄基-钴氧肟类发生热反应，可制得高产率的有机-4-甲苯磺酸酯。烯丙基钴肟主要产生，有时在某些情况下仅产生重排的烯砜。脂环族的3-烯基钴肟化合物产生相应的环丙基-羧甲基砜；环烯基乙基钴肟酯产生螺-1,1-环丙基-环烷基砜；环烷-2-烯基甲基钴肟生成双环[1.0。ñ]烷基砜。螺和双环烷基化合物也与其他自由基前体形成。认为反应是通过链机制发生的，其中不定存在或通过底物部分均相形成的钴肟（II）从甲苯磺酰碘中提取碘，生成甲苯磺酰基自由基，该自由基攻击钴肟的有机配体，优选在末端烯烃碳处，从而置换钴肟（II）并得到所观察到的有机产物。

  DOI：

  10.1016/0022-328x(85)87417-9

文献信息

• Préparation de cétones et d'alcools insaturés a partir de la méthylvinylcétone. Une synthése simple et efficace d'alcools isopréniques
  作者：R. Bloch

  DOI：10.1016/s0040-4020(01)91839-3

  日期：1983.1

  The preparation of olefinic ketones and alcohols by means of a retro Diels-Alder reaction is described. This process has been applied to high yield syntheses of linalool 6e, nerolidol 6f and the sesquiterpene alcohol 10 recently isolated from the alga Laurencia nidifica.

  描述了通过逆Diels-Alder反应制备烯烃酮和醇。该方法已用于最近从海藻Laurencia nidifica中分离出的芳樟醇6e，nerolidol 6f和倍半萜醇10的高产率合成中。
• 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.
• Ho, Tse-Lok; Hall, T. W., Synthetic Communications, 1981, vol. 11, # 5, p. 371 - 374
  作者：Ho, Tse-Lok、Hall, T. W.

  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：——
• US4105681A
  申请人：——

  公开号：US4105681A

  公开（公告）日：1978-08-08