(-)-dimethyl (2S,3aS,8aR)-8-(4-methoxybenzenesulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate | 162302-18-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (-)-dimethyl (2S,3aS,8aR)-8-(4-methoxybenzenesulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate
• 英文别名: dimethyl (2S,3aR,8bS)-4-(4-methoxyphenyl)sulfonyl-1,2,3a,8b-tetrahydropyrrolo[2,3-b]indole-2,3-dicarboxylate
• CAS: 162302-18-3
• 化学式: C₂₁H₂₂N₂O₇S
• 分子量: 446.481
• InChiKey: HXVMMJBYEOHGFP-YTQUADARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (-)-dimethyl (2S,3aS,8aR)-8-(4-methoxybenzenesulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate 、 碘甲烷 在 lithium diisopropyl amide 作用下， 生成 (-)-dimethyl (2R,3aR,8aS)-8-(4-methoxybenzenesulfonyl)-2-methyl-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate
  参考文献：
  名称：

  取代六氢吡咯并[2,3- b ]吲哚和相关体系的构象分析。磺酰胺SN键旋转受阻的不寻常例子。X射线晶体学和NMR研究

  摘要：

  该溶液的深入比较（CDCL 3，1的六氢吡咯并的H-NMR）和固态（X射线）的构象并[2,3- b ]吲哚4，5，和6制成。注意到与黄曲霉毒素呋喃[2，3- b ]苯并呋喃骨架的文献构型和与天然存在的六氢吡咯并吲哚毒扁豆碱的构型极为相似。在固态下，4 – 6中的磺酰胺N是非平面的，围绕SN键有不同程度的旋转。在溶液中，变温1 H-NMR证据指示关于磺酰胺基团的NS键的受阻旋转的4 - 6可能与锥体磺酰胺N原子的倒置有关。5与LDA的反应，然后用碘甲烷淬灭，导致烷基化，构型完全相反。

  DOI：

  10.1016/0040-4020(95)00001-o
• 作为产物：
  描述：

  dimethyl (2S,3aR,8bR)-4-(4-methoxyphenyl)sulfonyl-8b-phenylselanyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indole-2,3-dicarboxylate 在 偶氮二异丁腈 、 二苯基二硒醚 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以74%的产率得到(-)-dimethyl (2S,3aS,8aR)-8-(4-methoxybenzenesulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate
  参考文献：
  名称：

  On the Reaction of Tryptophan Derivatives with N-Phenylselenyl Phthalimide:  The Nature of the Kinetic and Thermodynamic Hexahydropyrrolo[2,3-b]indole Products. Alkylation of Tryptophan with Inversion of Configuration

  摘要：

  The cyclization of a range of tryptophan derivatives with N-phenylselenyl phthalimide leading to 3a-phenylselenyl-1,2,3,3a,8,8a-hexahydro[2,3b]pyrroloindoles has been studied. It is established that in each case the kinetic diastereomer has the C-2 substituent on the exo face of the diazabicyclo[3.3.0]octane skeleton, whereas the thermodynamic isomers have the C-2 substituent endo. A simple protocol for the alkylation of tryptophan, leading to alpha-substituted tryptophans with clean inversion of configuration, is presented.

  DOI：

  10.1021/jo991093+

文献信息

• Conformational analysis of substituted hexahydropyrrolo [2,3-b]indoles and related systems. An unusual example of hindered rotation about sulfonamide SN bonds. An X-ray crystallographic and NMR study
  作者：David Crich、Milan Bruncko、Swaminathan Natarajan、Boon K. Teo、Derek A. Tocher

  DOI：10.1016/0040-4020(95)00001-o

  日期：1995.2

  An indepth comparison of the solution (CDCl3, 1H-NMR) and solid state (X-ray) conformations of the hexahydropyrrolo[2,3-b]indoles 4, 5, and 6 is made. Close parallels with the literature conformations of the aflatoxin furo[2,3-b]benzofuran skeleton and with the conformation of the naturally occuring hexahydropyrrolindole physostigmine are noted. In the solid state the sulfonamide N in 4 – 6 is non-planar

  该溶液的深入比较（CDCL 3，1的六氢吡咯并的H-NMR）和固态（X射线）的构象并[2,3- b ]吲哚4，5，和6制成。注意到与黄曲霉毒素呋喃[2，3- b ]苯并呋喃骨架的文献构型和与天然存在的六氢吡咯并吲哚毒扁豆碱的构型极为相似。在固态下，4 – 6中的磺酰胺N是非平面的，围绕SN键有不同程度的旋转。在溶液中，变温1 H-NMR证据指示关于磺酰胺基团的NS键的受阻旋转的4 - 6可能与锥体磺酰胺N原子的倒置有关。5与LDA的反应，然后用碘甲烷淬灭，导致烷基化，构型完全相反。
• On the Reaction of Tryptophan Derivatives with <i>N</i>-Phenylselenyl Phthalimide:  The Nature of the Kinetic and Thermodynamic Hexahydropyrrolo[2,3-<i>b</i>]indole Products. Alkylation of Tryptophan with Inversion of Configuration
  作者：David Crich、Xianhai Huang

  DOI：10.1021/jo991093+

  日期：1999.9.1

  The cyclization of a range of tryptophan derivatives with N-phenylselenyl phthalimide leading to 3a-phenylselenyl-1,2,3,3a,8,8a-hexahydro[2,3b]pyrroloindoles has been studied. It is established that in each case the kinetic diastereomer has the C-2 substituent on the exo face of the diazabicyclo[3.3.0]octane skeleton, whereas the thermodynamic isomers have the C-2 substituent endo. A simple protocol for the alkylation of tryptophan, leading to alpha-substituted tryptophans with clean inversion of configuration, is presented.