(2R,3aR,8aS)-2-phenylselenyl-8-(toluene-4-sulfonyl)-3,3a,8,8a-hexahydro-2H-pyrrolo[2,3-b]indole-1-carboxylic acid methyl ester | 709030-60-4

• 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: (2R,3aR,8aS)-2-phenylselenyl-8-(toluene-4-sulfonyl)-3,3a,8,8a-hexahydro-2H-pyrrolo[2,3-b]indole-1-carboxylic acid methyl ester
• 英文别名: (2R,3aR,8aS)-2-phenylselanyl-8-(toluene-4-sulfonyl)-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1-carboxylic acid methyl ester；(2R)-methyl 2-phenylselanyl-8-tosyl-3,3a,8,8a-tetrahydropyrrolo[2,3-b]indole-1(2H)-carboxylate；methyl (2R,3aS,8bR)-4-(4-methylphenyl)sulfonyl-2-phenylselanyl-1,2,3a,8b-tetrahydropyrrolo[2,3-b]indole-3-carboxylate
• CAS: 709030-60-4
• 化学式: C₂₅H₂₄N₂O₄SSe
• 分子量: 527.503
• InChiKey: IJYQPWICNSWDMS-JRFVFWCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  75.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3aR,8aS)-2-phenylselenyl-8-(toluene-4-sulfonyl)-3,3a,8,8a-hexahydro-2H-pyrrolo[2,3-b]indole-1-carboxylic acid methyl ester 在 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以68%的产率得到4-methyl-N-[2-(1H-pyrrol-3-yl)phenyl]benzenesulfonamide
  参考文献：
  名称：

  A contribution to the elucidation of the biosynthesis of 3-chloro-4-(3′-chloro-2′-nitrophenyl)-1H-pyrrole (pyrrolnitrin)

  摘要：

  Selective openings of the ring B of the derivative hexapyrroloindol in basic conditions confirm the rearrangement of the tryptophan to aminoarylpyrrol, analogously to the step catalyzed by the enzyme prnB in the biosynthesis of pyrrolnitrin. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.034
• 作为产物：
  描述：

  、 二苯基二硒醚 在 氯化1-氧杂-2-羰基-3-硫杂中氮茚正离子 、 三乙胺 作用下， 生成 (2R,3aR,8aS)-2-phenylselenyl-8-(toluene-4-sulfonyl)-3,3a,8,8a-hexahydro-2H-pyrrolo[2,3-b]indole-1-carboxylic acid methyl ester
  参考文献：
  名称：

  A contribution to the elucidation of the biosynthesis of 3-chloro-4-(3′-chloro-2′-nitrophenyl)-1H-pyrrole (pyrrolnitrin)

  摘要：

  Selective openings of the ring B of the derivative hexapyrroloindol in basic conditions confirm the rearrangement of the tryptophan to aminoarylpyrrol, analogously to the step catalyzed by the enzyme prnB in the biosynthesis of pyrrolnitrin. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.034

文献信息

• Endo-Selective Quenching of Hexahydropyrrolo[2,3-<i>b</i>]indole-Based <i>N</i>-Acyliminium Ions
  作者：Rosa L. Meza-León、David Crich、Sylvain Bernès、Leticia Quintero

  DOI：10.1021/jo049757p

  日期：2004.5.1

  Radical decarboxylation Of L-tryptophan-derived (2S,3aR,8aS)-8-arylsulfonyl-1,2-di(methoxycarbonyl)-1,2,3,- 3a,8,8a-hexahydro-2H-pyrrolo[2,3-b]indoles 8 and 9 in the presence of diphenyl diselenide results in the endo-selective formation of (2R,3a-R,SaS)-8-arylsulfonyl-1-methoxycarbonyl-2-phenylselenyl-1,2,3,3a,8,8a-hexahydro-2H-pyrrolo[2,3- b]indoles 10 and 11. These selenides, in conjunction with Lewis acids, serves as precursors to the corresponding N-acyl iminium ions, which undego selective endo-face quenching by allyltributylstannane, allyltrimethylsilane, propargyltrimethylsilane, and trimethylsilylcyanide. Stereochemical assignments rest on NMR data and crystallographic studies. The endo-selective nature of these reactions is interpreted in terms of minimization of allylic strain at the transition state for nucleophilic attack on the N-acyl iminum ion.
• A contribution to the elucidation of the biosynthesis of 3-chloro-4-(3′-chloro-2′-nitrophenyl)-1H-pyrrole (pyrrolnitrin)
  作者：Ana Bertha Vázquez、Sylvain Bernès、Aurelio Ortíz、Leticia Quintero、Rosa L. Meza-León

  DOI：10.1016/j.tetlet.2009.01.034

  日期：2009.4

  Selective openings of the ring B of the derivative hexapyrroloindol in basic conditions confirm the rearrangement of the tryptophan to aminoarylpyrrol, analogously to the step catalyzed by the enzyme prnB in the biosynthesis of pyrrolnitrin. (C) 2009 Elsevier Ltd. All rights reserved.