2-[Bis(2,3-dihydro-1,4-benzodioxin-6-yl)methyl]aniline | 898799-89-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: 2-[Bis(2,3-dihydro-1,4-benzodioxin-6-yl)methyl]aniline
• 英文别名: 2-[bis(2,3-dihydro-1,4-benzodioxin-6-yl)methyl]aniline
• CAS: 898799-89-8
• 化学式: C₂₃H₂₁NO₄
• 分子量: 375.424
• InChiKey: KAZMUYFVQWXRSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  62.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[Bis(2,3-dihydro-1,4-benzodioxin-6-yl)methyl]aniline 在 三氯化铝 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 、 1,1,2,2-四氯乙烷 为溶剂， 反应 24.0h， 生成 2,4-bis(2,3-dihydro-1,4-benzodioxin-6-yl)-4H-3,1-benzothiazine
  参考文献：
  名称：

  Aromatic ring transfer—a new synthesis of 2,4-diaryl-4H-3,1-benzothiazines

  摘要：

  A new synthetic approach to 2,4-diaryl-4H-3,1-benzothiazines is described based on the rearrangement of 2-isothiocyano triarylmethanes in the presence of AlCl3. An aryl ring is found to migrate to the carbon atom of an isothiocyano group followed by intramolecular cyclization as a result of electrophilic attack of the benzhydryl carbocation on the sulfur atom. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.04.010
• 作为产物：
  描述：

  1,4-苯并二恶烷 在 镍 三氯化铝 、 一水合肼 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 2-[Bis(2,3-dihydro-1,4-benzodioxin-6-yl)methyl]aniline
  参考文献：
  名称：

  Aromatic ring transfer—a new synthesis of 2,4-diaryl-4H-3,1-benzothiazines

  摘要：

  A new synthetic approach to 2,4-diaryl-4H-3,1-benzothiazines is described based on the rearrangement of 2-isothiocyano triarylmethanes in the presence of AlCl3. An aryl ring is found to migrate to the carbon atom of an isothiocyano group followed by intramolecular cyclization as a result of electrophilic attack of the benzhydryl carbocation on the sulfur atom. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.04.010

文献信息

• Aryl Ring Migration Reaction in the Synthesis of 2,4-Diaryl-4H-3,1-benzothiazines
  作者：Alexander Butin、Fatima Tsiunchik、Vladimir Abaev、Andrey Gutnov、Dmitry Cheshkov

  DOI：10.1055/s-0029-1217399

  日期：2009.8

  thiocarbamoylation reaction also takes place, and 5,11-dihydro-6H-dibenzo[b,e]azepine-5-thiones are isolated as byproducts. Factors influencing the mechanism and selectivity of the reaction are discussed. The corresponding 1-(arylmethyl)-2-isothiocyanatobenzene derivatives were also synthesized, and their behavior under Friedel-Crafts reaction conditions was investigated to confirm the crucial role

  描述了1-（二芳基甲基）-2-异硫氰酸根合苯到2,4-二芳基-4 H -3,1-苯并噻嗪衍生物的新的重排。在Friedel-Crafts条件下用三氯化铝处理起始化合物导致芳基取代基通过亲电的ipso取代机理迁移，然后环化形成3，1-苯并噻嗪环。预期的分子内硫代氨基甲酰化反应也会发生，并且5,11-dihydro-6 H -dibenzo [ b，e分离出[]氮杂-5-硫酮副产物。讨论了影响反应机理和选择性的因素。还合成了相应的1-（芳基甲基）-2-异硫氰酸根合苯衍生物，并研究了它们在Friedel-Crafts反应条件下的行为，以证实中间体二苯甲基/苄基阳离子的稳定性在确定反应过程中的关键作用。 1-（二芳基甲基）-2-异硫氰酸根合苯-Friedel-Crafts-重排-芳基迁移-3,1-苯并噻嗪
• Aromatic ring transfer—a new synthesis of 2,4-diaryl-4H-3,1-benzothiazines
  作者：Vladimir T. Abaev、Fatima A. Tsiunchik、Andrey V. Gutnov、Alexander V. Butin

  DOI：10.1016/j.tetlet.2006.04.010

  日期：2006.6

  A new synthetic approach to 2,4-diaryl-4H-3,1-benzothiazines is described based on the rearrangement of 2-isothiocyano triarylmethanes in the presence of AlCl3. An aryl ring is found to migrate to the carbon atom of an isothiocyano group followed by intramolecular cyclization as a result of electrophilic attack of the benzhydryl carbocation on the sulfur atom. (c) 2006 Elsevier Ltd. All rights reserved.