7-[hydroxy(phenyl)methyl]-6-(4-methylphenylsulfonamido)-2,3-dihydro-1,4-benzodioxine | 886493-41-0

• 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: 7-[hydroxy(phenyl)methyl]-6-(4-methylphenylsulfonamido)-2,3-dihydro-1,4-benzodioxine
• 英文别名: N-(7-(Hydroxy(phenyl)methyl)-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-4-methylbenzenesulfonamide；N-[7-[hydroxy(phenyl)methyl]-2,3-dihydro-1,4-benzodioxin-6-yl]-4-methylbenzenesulfonamide
• CAS: 886493-41-0
• 化学式: C₂₂H₂₁NO₅S
• 分子量: 411.478
• InChiKey: SCKBXDTUOHBMOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  93.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-[hydroxy(phenyl)methyl]-6-(4-methylphenylsulfonamido)-2,3-dihydro-1,4-benzodioxine 在 盐酸 、 氢氧化钾 、 对甲苯磺酸 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 4-(8-phenyl-2,3-dihydro-6H-[1,4]dioxino[2,3-f]indol-7-yl)-2-butanone
  参考文献：
  名称：

  Simple route to 3-(2-indolyl)-1-propanones via a furan recyclization reaction

  摘要：

  A simple route to 1-R-3-(2-indolyl)-1-propanones has been elaborated based on recyclization of 2-(2-aminobenzyl)furan derivatives. Being a modification of the Reissert indole synthesis, our approach employs the furan ring as a source of carbonyl function. This approach is general and allows varying of substituents in aromatic ring as well as in 3-position of indole nucleus. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.10.056
• 作为产物：
  描述：

  2,3-dihydro-1,4-benzodioxin-6-yl(phenyl)methanone 在 吡啶 、 sodium tetrahydroborate 、 硝酸 、 铁粉 、 溶剂黄146 作用下， 以 乙醇 、 水 、 乙酸乙酯 为溶剂， 反应 7.5h， 生成 7-[hydroxy(phenyl)methyl]-6-(4-methylphenylsulfonamido)-2,3-dihydro-1,4-benzodioxine
  参考文献：
  名称：

  Simple route to 3-(2-indolyl)-1-propanones via a furan recyclization reaction

  摘要：

  A simple route to 1-R-3-(2-indolyl)-1-propanones has been elaborated based on recyclization of 2-(2-aminobenzyl)furan derivatives. Being a modification of the Reissert indole synthesis, our approach employs the furan ring as a source of carbonyl function. This approach is general and allows varying of substituents in aromatic ring as well as in 3-position of indole nucleus. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.10.056

文献信息

• Oxidative Furan-to-Indole Rearrangement. Synthesis of 2-(2-Acylvinyl)indoles and Flinderole C Analogues
  作者：Anton S. Makarov、Anton A. Merkushev、Maxim G. Uchuskin、Igor V. Trushkov

  DOI：10.1021/acs.orglett.6b00805

  日期：2016.5.6

  Oxidative rearrangement of 2-(2-aminobenzyl)furans affording 2-(2-acylvinyl)indoles in a stereocontrolled manner in good-to-excellent yields has been developed. Thus, (2-aminobenzyl)furans with electron-releasing alkoxy substituents in the phenyl group form only E-isomers of 2-(2-acylvinyl)indoles. Conversely, substrates without such substituents produce target products as Z-isomers exclusively. A

  已经开发出以立体控制的方式以良好至优异的产率提供2-（2-酰基乙烯基）吲哚的2-（2-氨基苄基）呋喃的氧化重排。因此，在苯基中具有释放电子的烷氧基取代基的（2-氨基苄基）呋喃仅形成2-（2-酰基乙烯基）吲哚的E-异构体。相反，没有这种取代基的底物仅产生目标产物，如Z-异构体。已开发出一种短的非对映选择性方法，用于将获得的2-（2-酰基乙烯基）吲哚转化为抗疟疾的双吲哚生物碱氟代烯AC类似物。
• Synthesis of Indoles by Domino Reaction of 2-(Tosylamino)benzyl Alcohols with Furfurylamines: Two Opposite Reactivity Modes of the α-Carbon of the Furan Ring in One Process
  作者：Maxim G. Uchuskin、Natalia V. Molodtsova、Sergey A. Lysenko、Vladimir N. Strel'nikov、Igor V. Trushkov、Alexander V. Butin

  DOI：10.1002/ejoc.201301762

  日期：2014.4

  An unusual domino reaction where the same furan α-carbon atom reacts initially as a nucleophile and then as an electrophile is reported. In the presence of acid, N-tosylfurfurylamines react with 2-(tosylamino)benzyl alcohols to afford 2-(2-acylvinyl)indoles. The reaction proceeds by Friedel–Crafts alkylation at the C(2) atom of furan followed by acid-catalyzed intramolecular nucleophilic attack of

  报道了一种不寻常的多米诺反应，其中相同的呋喃 α-碳原子最初作为亲核试剂反应，然后作为亲电试剂反应。在酸存在下，N-甲苯磺酰基糠胺与 2-（甲苯磺酰基氨基）苄醇反应生成 2-（2-酰基乙烯基）吲哚。该反应通过在呋喃的 C(2) 原子上进行 Friedel-Crafts 烷基化，然后酸催化邻氨基对相同碳原子的分子内亲核攻击进行。用邻苯二甲酰亚胺替换甲苯磺酰氨基离去基团可以生成不同类型的吲哚，同时保留 C(2) 的两亲性质。当使用 N-糠基苯甲酰胺时，可以得到两种类型的吲哚。
• Simple route to 3-(2-indolyl)-1-propanones via a furan recyclization reaction
  作者：Alexander V. Butin、Sergey K. Smirnov、Tatyana A. Stroganova、Wolfgang Bender、Gennady D. Krapivin

  DOI：10.1016/j.tet.2006.10.056

  日期：2007.1

  A simple route to 1-R-3-(2-indolyl)-1-propanones has been elaborated based on recyclization of 2-(2-aminobenzyl)furan derivatives. Being a modification of the Reissert indole synthesis, our approach employs the furan ring as a source of carbonyl function. This approach is general and allows varying of substituents in aromatic ring as well as in 3-position of indole nucleus. (c) 2006 Elsevier Ltd. All rights reserved.