2-(2-hydroxybenzylamino)acetaldehyde dimethyl acetal | 817160-26-2

• 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-(2-hydroxybenzylamino)acetaldehyde dimethyl acetal
• 英文别名: 2-(2,2-dimethoxyethylaminomethyl)phenol；2-[(2,2-Dimethoxyethylamino)methyl]phenol
• CAS: 817160-26-2
• 化学式: C₁₁H₁₇NO₃
• 分子量: 211.261
• InChiKey: KYVNEUSDAJQXCG-UHFFFAOYSA-N

物化性质

• 沸点：
  304.7±32.0 °C(Predicted)
• 密度：
  1.099±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  50.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-hydroxybenzylamino)acetaldehyde dimethyl acetal 在 cerium(III) chloride heptahydrate 、 硫酸 作用下， 以 水 、 乙腈 为溶剂， 反应 48.0h， 生成 1-(2-hydroxybenzyl)benzo[f]indole-4,9-dione
  参考文献：
  名称：

  Ultrasound assisted one-pot synthesis of benzo-fused indole-4,9-dinones from 1,4-naphthoquinone and α-aminoacetals

  摘要：

  A one-pot synthesis of benzo[f]indole-4,9-diones from 1,4-naphthoquinone with alpha-aminoacetals has been developed. This method provides a straightforward synthesis of benzo[f]indole-4,9-diones via intramolecular nucleophilic attack of aminoquinones to aldehydes under mild reaction conditions. The detailed mechanism was also investigated. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2016.04.031
• 作为产物：
  描述：

  水杨醛 、 氨基乙醛缩二甲醇 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以43.6%的产率得到2-(2-hydroxybenzylamino)acetaldehyde dimethyl acetal
  参考文献：
  名称：

  Ultrasound assisted one-pot synthesis of benzo-fused indole-4,9-dinones from 1,4-naphthoquinone and α-aminoacetals

  摘要：

  A one-pot synthesis of benzo[f]indole-4,9-diones from 1,4-naphthoquinone with alpha-aminoacetals has been developed. This method provides a straightforward synthesis of benzo[f]indole-4,9-diones via intramolecular nucleophilic attack of aminoquinones to aldehydes under mild reaction conditions. The detailed mechanism was also investigated. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2016.04.031

文献信息

• Synthesis of tetrahydrobenzoxazepine acetals with electron-withdrawing groups on the nitrogen atom. Novel scaffolds endowed with anticancer activity against breast cancer cells
  作者：Mónica Díaz-Gavilán、Fernando Rodríguez-Serrano、José A. Gómez-Vidal、Juan A. Marchal、Antonia Aránega、Miguel Á. Gallo、Antonio Espinosa、Joaquín M. Campos

  DOI：10.1016/j.tet.2004.09.072

  日期：2004.12

  Synthetic approaches that have led to (RS)-3-methoxy-N-substituded-1,2,3,5-tetrahydro-4,1-benzoxazepines with different electron-withdrawing groups, and (RS)-2-methoxy-N-trifluoroacetyl-2,3,4,5-tetrahydro-1,4-benzoxazepine are described. These novel synthons that were designed to be used as scaffolds for the preparation of new 0,N-acetals as anticancer agents, unexpectedly proved to show antiproliferative activity against the MCF-7 breast cancer cell line. It has been found that substituents on the nitrogen atom have an influence on biological activity. In particular, the presence of a trifluoroacetyl moiety on the nitrogen atom leads to amides displaying interesting in vitro antitumour activities. (C) 2004 Elsevier Ltd. All rights reserved.
• Ultrasound assisted one-pot synthesis of benzo-fused indole-4,9-dinones from 1,4-naphthoquinone and α-aminoacetals
  作者：Quang H. Luu、Jorge D. Guerra、Cecilio M. Castañeda、Manuel A. Martinez、Jong Saunders、Benjamin A. Garcia、Brenda V. Gonzales、Anushritha R. Aidunuthula、Shizue Mito

  DOI：10.1016/j.tetlet.2016.04.031

  日期：2016.5

  A one-pot synthesis of benzo[f]indole-4,9-diones from 1,4-naphthoquinone with alpha-aminoacetals has been developed. This method provides a straightforward synthesis of benzo[f]indole-4,9-diones via intramolecular nucleophilic attack of aminoquinones to aldehydes under mild reaction conditions. The detailed mechanism was also investigated. (C) 2016 Elsevier Ltd. All rights reserved.