<1-(phenylsulfonyl)indol-2-yl>methyl acetate | 143774-54-3

• 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)indol-2-yl>methyl acetate
• 英文别名: 2-acetoxymethyl-1-(phenylsulfonyl)indole；[1-(Benzenesulfonyl)indol-2-yl]methyl acetate
• CAS: 143774-54-3
• 化学式: C₁₇H₁₅NO₄S
• 分子量: 329.376
• InChiKey: WZKNWYVYOKJUOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-苯磺酸吲哚 在 sodium acetate 、 lithium diisopropyl amide 作用下， 以 苯 为溶剂， 反应 9.5h， 生成 <1-(phenylsulfonyl)indol-2-yl>methyl acetate
  参考文献：
  名称：

  Syntheses and Diels-Alder cycloaddition reactions of 4H-furo[3,4-b]indoles. A regiospecific Diels-Alder synthesis of ellipticine

  摘要：

  Seven examples of the novel 4H-furo[3,4-b]indole ring system (3-9)-a stable, synthetic analogue of indole-2,3-quinodimethane-have been synthesized in 6-8 steps from simple indoles in overall yields of 21-28%. These 4H-furo[3,4-b]indoles undergo Diels-Alder reactions with several dienophiles (dimethyl acetylenedicarboxylate, N-phenylmaleimide, benzyne), including ethyl acrylate, which reacts regiospecifically with furoindole 4 to afford a single carbazole ester (59). This result, predicted by molecular orbital calculations, was used to design and execute a regiospecific Diels-Alder synthesis of the antitumor alkaloid ellipticine (63). Thus, the trimethylsilyl triflate-induced reaction between furoindole 4 and dihydropyridone 68b is greater-than-or-equal-to 99% regioselective and affords lactam 70b in 89% yield. Further manipulation gives ellipticine (63) with no detectable (<1%) isoellipticine (64) in the crude product.

  DOI：

  10.1021/jo00048a021

文献信息

• Manganese(III) Acetate Oxidation of Alkyl Substituted 1-(Phenylsulfonyl)indoles
  作者：Daniel M. Ketcha、Qin Zhou、David Grossie

  DOI：10.1080/00397919408011507

  日期：1994.2

  Abstract Methyl substituted 1-(phenylsulfonyl)indolines undergo tandem oxidation of the indoline ring and a C-2 methyl group. If there is no alkyl substituent at the C-2 position, nuclear acetoxylation can occur to afford oxindoles.

  摘要 甲基取代的 1-（苯磺酰基）二氢吲哚发生二氢吲哚环和 C-2 甲基的串联氧化。如果在 C-2 位没有烷基取代基，核乙酰氧基化会发生以提供羟吲哚。