1-dichloromethyl-3,4,5-trimethoxybenzene | 136269-33-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-dichloromethyl-3,4,5-trimethoxybenzene
• 英文别名: 3,4,5-Trimethoxy(dichloromethyl)benzene；5-(Dichloromethyl)-1,2,3-trimethoxybenzene
• CAS: 136269-33-5
• 化学式: C₁₀H₁₂Cl₂O₃
• 分子量: 251.109
• InChiKey: JRNYWBDSGQQINH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-dichloromethyl-3,4,5-trimethoxybenzene 在 potassium tert-butylate 、 silica gel 作用下， 以 四氯化碳 、 乙二醇二甲醚 为溶剂， 生成 5-(2,4-dimethylpenta-1,3-dien-3-yl)-1,2,3-trimethoxybenzene
  参考文献：
  名称：

  Baird, Mark S.; Dacre, Richard; Tomkinson, Jeremy, Journal of the Chemical Society. Perkin transactions I, 1992, # 5, p. 535 - 538

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 在 氯化亚砜 作用下， 生成 1-dichloromethyl-3,4,5-trimethoxybenzene
  参考文献：
  名称：

  Cr 催化下二卤代烷烃的化学选择性三组分偕交叉偶联：通过金属卡宾中间体快速获得叔烷烃和季烷烃

  摘要：

  三组分孪生偶联是通过设计铬催化系统来实现的，该系统使用二卤代烷烃选择性地与有机镁和氯硅烷/甲苯磺酸烷基酯反应。这些新开发的反应可有效通过具有新颖内球自由基耦合机制的Cr卡宾中间体快速形成叔烷烃和季烷烃，在合成和药物化学中显示出巨大的潜力。

  DOI：

  10.1002/anie.202312856

文献信息

• Process for opening cyclopropane rings
  申请人：SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ B.V.

  公开号：EP0432818A2

  公开（公告）日：1991-06-19

  Process for ring opening compounds of the formula in which R¹ is heteroaryl or aryl, R² is a leaving group, R³, R⁴, R⁵ and R⁶ are independently selected from hydrogen, alkyl, aralkyl, aryl, heteroaryl and alkenyl, provided that at least one of the groups R³ to R⁶ is other than hydrogen, by breaking the bond joining the carbon atom attached to R³ and the carbon atom attached to R⁶ in organic solution using silica,giving useful diene or allyl derivatives, certain of which are novel.

  式的开环化合物的工艺 其中 R¹ 为杂芳基或芳基，R² 为离去基团，R³、R⁴、R⁵ 和 R⁶ 独立选自氢、烷基、芳基、芳基、杂芳基和烯基，条件是 R³ 至 R⁶ 中至少有一个基团不是氢、在有机溶液中用二氧化硅断开连接 R³ 的碳原子和连接 R⁶ 的碳原子的键，得到有用的二烯或烯丙基衍生物，其中某些衍生物是新颖的。
• Possible reaction pathways for the formation of 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX)
  作者：Vivi-Ann Långvik、Osmo Hormi

  DOI：10.1016/0045-6535(94)90329-8

  日期：1994.3

  Three compounds, 3,4,5-trimethoxybenzaldehyde (I), 1-dichloromethyl-3,4,5-trimethoxy-benzene (II) and 3,4,5-trimethoxyphenylacetic acid (III) were treated with aqueous chlorine at pH 2. Aqueous chlorination of the three compounds increased the formation of MX (3-chloro-4-dichloromethyl-5(2H)-hydroxy-furanone) and E-MX (E 2-chloro-3-dichloromethyl-4-oxo-butenoic acid) in the order I > II > III. By H-1-NMR spectroscopy and gas chromatography it was shown that II hydrolizes readily to I in water. It is known that III is converted to II in chlorination reactions. We suggest that the (formed) aldehyde group remains intact during the formation of MX and E-MX from these three compounds. They could thus form MX and E-MX, via similar mechanisms. This suggested mechanism may also occur when phenolic precursor structures present in humic material are treated with chlorine in the process of drinking water production.
• US5126461A
  申请人：——

  公开号：US5126461A

  公开（公告）日：1992-06-30
• Baird, Mark S.; Dacre, Richard; Tomkinson, Jeremy, Journal of the Chemical Society. Perkin transactions I, 1992, # 5, p. 535 - 538
  作者：Baird, Mark S.、Dacre, Richard、Tomkinson, Jeremy

  DOI：——

  日期：——
• Chemoselective Three‐Component Geminal Cross Couplings of Dihaloalkanes with Cr Catalysis: Rapid Access to Tertiary and Quaternary Alkanes via a Metal–Carbene Intermediate
  作者：Sha Wang、Linhong Long、Xiaoyu Zhang、Liang Ling、Hui Chen、Xiaoming Zeng

  DOI：10.1002/anie.202312856

  日期：2023.10.26

  The three-component geminal couplings have been achieved by design of a chromium catalytic system using dihaloalkanes to selective react with organomagnesium and chlorosilanes/alkyl tosylates. These newly developed reactions are effective for rapidly forming tertiary and quaternary alkanes via a Cr carbene intermediate with a novel inner-sphere radical coupling mechanism, showing great potential in

  三组分孪生偶联是通过设计铬催化系统来实现的，该系统使用二卤代烷烃选择性地与有机镁和氯硅烷/甲苯磺酸烷基酯反应。这些新开发的反应可有效通过具有新颖内球自由基耦合机制的Cr卡宾中间体快速形成叔烷烃和季烷烃，在合成和药物化学中显示出巨大的潜力。