1-bromo-4,5-dimethoxy-2-[(methoxy)(phenyl)methyl]benzene | 1638643-98-7

• 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: 1-bromo-4,5-dimethoxy-2-[(methoxy)(phenyl)methyl]benzene
• 英文别名: 1-bromo-4,5-dimethoxy-2-[methoxy(phenyl)methyl]benzene
• CAS: 1638643-98-7
• 化学式: C₁₆H₁₇BrO₃
• 分子量: 337.213
• InChiKey: IFWBGSRXBNXOSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-bromo-4,5-dimethoxy-2-[(methoxy)(phenyl)methyl]benzene 在 正丁基锂 、 氢溴酸 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 25.25h， 生成 (Z)-5,6-dimethoxy-3,N-diphenylbenzo[c]thiophen-1(3H)-imine
  参考文献：
  名称：

  Synthesis of N-Substituted (Z)-3-Arylbenzo[c]thiophen-1(3H)-imines by the Reaction of 1-[Aryl(methoxy)methyl]-2-lithiobenzenes with Isothiocyanates Followed by Acid-Mediated Cyclization

  摘要：

  A simple procedure for the preparation of N-substituted (Z)-3-arylbenzo[c]thiophen-1(3H)-imines has been developed. Thus, bromine/lithium exchange between 1-[aryl(methoxy)methyl]-2-bromobenzenes and butyllithium, followed by reaction of the resulting 1-[aryl(methoxy)methyl]-2-lithiobenzenes with aliphatic and aromatic isothiocyanates, yields the corresponding N-substituted 2-[aryl(methoxy)methyl]benzothioamides. These were treated with concentrated hydrobromic acid to give the desired products.

  DOI：

  10.3987/com-14-13154
• 作为产物：
  描述：

  (2-bromo-4,5-dimethoxyphenyl)phenylmethanol 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 1.0h， 以91%的产率得到1-bromo-4,5-dimethoxy-2-[(methoxy)(phenyl)methyl]benzene
  参考文献：
  名称：

  Synthesis of N-Substituted (Z)-3-Arylbenzo[c]thiophen-1(3H)-imines by the Reaction of 1-[Aryl(methoxy)methyl]-2-lithiobenzenes with Isothiocyanates Followed by Acid-Mediated Cyclization

  摘要：

  A simple procedure for the preparation of N-substituted (Z)-3-arylbenzo[c]thiophen-1(3H)-imines has been developed. Thus, bromine/lithium exchange between 1-[aryl(methoxy)methyl]-2-bromobenzenes and butyllithium, followed by reaction of the resulting 1-[aryl(methoxy)methyl]-2-lithiobenzenes with aliphatic and aromatic isothiocyanates, yields the corresponding N-substituted 2-[aryl(methoxy)methyl]benzothioamides. These were treated with concentrated hydrobromic acid to give the desired products.

  DOI：

  10.3987/com-14-13154

文献信息

• Synthesis of Substituted Biaryls through Gold-Catalyzed Petasis-Ferrier Rearrangement of Propargyl Ethers
  作者：Kamalkishore Pati、Igor V. Alabugin

  DOI：10.1002/ejoc.201402469

  日期：2014.7

  Au-catalyzed cycloisomerization of aryl propargyl ethers provides controlled transition from alkyne to carbonyl chemistry followed up by a Petasis–Ferrier rearrangement/aromatization cascade leading to substituted biaryls with functionalized naphthalene cores.

  芳基炔丙基醚的金催化环异构化提供了从炔烃到羰基化学的受控转变，随后是 Petasis-Ferrier 重排/芳构化级联，导致取代的联芳基具有功能化的萘核。
• Synthesis of N,N-Disubstituted 1-Aryl-1,3-dihydro-2H-isoindole-2-carbothioamides
  作者：Kazuhiro Kobayashi、Yuuho Shigemura、Miyuki Tanmatsu

  DOI：10.3987/com-16-13421

  日期：——

  A convenient method for the synthesis of N,N-disubstituted 1-aryl-1,3-dihydro-2H-isoindole-2-carbothioamides starting from 2-[aryl(methoxy)methyl]phenyl bromides is described. Thus, the reaction of 1-[aryl(methoxy)methyl]-2-(isothiocyanatomethyl)benzenes, derived from the starting materials by an easily operated five-step sequence under mild conditions, with secondary amines provides the corresponding thiourea derivatives, which cyclize on treatment with methanesulfonic acid to afford the desired products.