1-(Phenylsulfonyl)-2-(α-hydroxy-3,4,5-trimethoxybenzyl)indole-3-carbaldehyde | 1027542-04-6

• 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-(Phenylsulfonyl)-2-(α-hydroxy-3,4,5-trimethoxybenzyl)indole-3-carbaldehyde
• 英文别名: 1-(Benzenesulfonyl)-2-[hydroxy-(3,4,5-trimethoxyphenyl)methyl]indole-3-carbaldehyde
• CAS: 1027542-04-6
• 化学式: C₂₅H₂₃NO₇S
• 分子量: 481.526
• InChiKey: LUVJSCGRKORPRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 1-(Phenylsulfonyl)-2-(α-hydroxy-3,4,5-trimethoxybenzyl)indole-3-carbaldehyde 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 1-(Phenylsulfonyl)-2-(α-acetoxy-3,4,5-trimethoxybenzyl)indole-3-carbaldehyde
  参考文献：
  名称：

  An Efficient Synthesis of Heterocyclic Analogs of 1-Arylnaphthalene Lignans

  摘要：

  The heterocyclic analogs 5a-f, 16, and 20 of 1-arylnaphthalene lignans were synthesized by Diels-Alder reactions of acetoxy aldehydes 11a-f, 14, and 18 with dimethyl acetylenedicarboxylate. A pathway for formation of 5a-f, 16, and 20 through the intermediacy of heteroaromatic isobenzofurans derived from acetoxy aldehydes is discussed.

  DOI：

  10.1021/jo00103a029
• 作为产物：
  描述：

  1-(Phenylsulfonyl)indole-3-carbaldehyde dimethyl acetal 在 盐酸 、 正丁基锂 、 四甲基乙二胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 14.0h， 生成 1-(Phenylsulfonyl)-2-(α-hydroxy-3,4,5-trimethoxybenzyl)indole-3-carbaldehyde
  参考文献：
  名称：

  An Efficient Synthesis of Heterocyclic Analogs of 1-Arylnaphthalene Lignans

  摘要：

  The heterocyclic analogs 5a-f, 16, and 20 of 1-arylnaphthalene lignans were synthesized by Diels-Alder reactions of acetoxy aldehydes 11a-f, 14, and 18 with dimethyl acetylenedicarboxylate. A pathway for formation of 5a-f, 16, and 20 through the intermediacy of heteroaromatic isobenzofurans derived from acetoxy aldehydes is discussed.

  DOI：

  10.1021/jo00103a029

文献信息

• An Efficient Synthesis of Heterocyclic Analogs of 1-Arylnaphthalene Lignans
  作者：Tooru Kuroda、Masami Takahashi、Tsuyoshi Ogiku、Hiroshi Ohmizu、Takashi Nishitani、Kazuhiko Kondo、Tameo Iwasaki

  DOI：10.1021/jo00103a029

  日期：1994.12

  The heterocyclic analogs 5a-f, 16, and 20 of 1-arylnaphthalene lignans were synthesized by Diels-Alder reactions of acetoxy aldehydes 11a-f, 14, and 18 with dimethyl acetylenedicarboxylate. A pathway for formation of 5a-f, 16, and 20 through the intermediacy of heteroaromatic isobenzofurans derived from acetoxy aldehydes is discussed.