1,2-dibenzyl 8-ethyl (2S,3aR,8aS)-3,3a-dihydropyrrolo[2,3-b]indole-1,2,8(2H,8aH)-tricarboxylate | 1214939-11-3

• 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: 1,2-dibenzyl 8-ethyl (2S,3aR,8aS)-3,3a-dihydropyrrolo[2,3-b]indole-1,2,8(2H,8aH)-tricarboxylate
• 英文别名: 2-O,3-O-dibenzyl 4-O-ethyl (2S,3aS,8bR)-1,2,3a,8b-tetrahydropyrrolo[2,3-b]indole-2,3,4-tricarboxylate
• CAS: 1214939-11-3
• 化学式: C₂₉H₂₈N₂O₆
• 分子量: 500.551
• InChiKey: RYVVDFZMUWWXEA-DMTNHVFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  85.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2-dibenzyl 8-ethyl (2S,3aR,8aS)-3,3a-dihydropyrrolo[2,3-b]indole-1,2,8(2H,8aH)-tricarboxylate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以100%的产率得到8-ethoxycarbonyl (2S,3aR,8aS)-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylic acid
  参考文献：
  名称：

  化学酶：受天然产物启发的一类新型结构刚性三环两栖有机催化剂

  摘要：

  基于六氢吡咯并[2,3- b ]吲哚骨架作为新型的化学酶，合理设计了新型结构刚性的三环两性手性催化剂。这种新型的化学酶具有结构刚性的三环骨架和手性囊，为不对称诱导提供了组织良好的手性环境，以及疏水性囊，使有机催化反应在有机溶剂和水中均能顺利进行。

  DOI：

  10.1021/ol9029758
• 作为产物：
  描述：

  dibenzyl (2S)-3,3a,8,8a-tetrahydropyrrolo[2,3-b]indol-1,2 (2H)-dicarboxylate 、 氯甲酸乙酯 在 sodium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 以86%的产率得到1,2-dibenzyl 8-ethyl (2S,3aR,8aS)-3,3a-dihydropyrrolo[2,3-b]indole-1,2,8(2H,8aH)-tricarboxylate
  参考文献：
  名称：

  化学酶：受天然产物启发的一类新型结构刚性三环两栖有机催化剂

  摘要：

  基于六氢吡咯并[2,3- b ]吲哚骨架作为新型的化学酶，合理设计了新型结构刚性的三环两性手性催化剂。这种新型的化学酶具有结构刚性的三环骨架和手性囊，为不对称诱导提供了组织良好的手性环境，以及疏水性囊，使有机催化反应在有机溶剂和水中均能顺利进行。

  DOI：

  10.1021/ol9029758

文献信息

• NOVEL TRICYCLIC CHIRAL COMPOUNDS AND THEIR USE IN ASYMMETRIC CATALYSIS
  申请人：Loh Teck Peng

  公开号：US20110269972A1

  公开（公告）日：2011-11-03

  The present invention relates to a compound of general Formula (XX), its formation and its use in asymmetric catalysis. In Formula (XX) R and R 31 are independently —COOR 3 , —R 4 COOR 3 , —R 4 CHO, —R 4 COR 3 , —R 4 CONR 5 R 6 , —R 4 COX, —R 4 OP(═O)(OH) 2 , —R 4 P(═O)(OH) 2 ), —R 4 C(O)C(R 3 )CR 5 R 6 and —R 4 CO 2 COR 3 . In addition, R 31 may also be hydrogen. R 3 , R 5 and R 6 are independently hydrogen, an aliphatic group with a main chain having 1 to about 20 carbon atoms, an alicyclic group, an aromatic group, an arylaliphatic group or an arylalicyclic group, comprising 0 to about 3 heteroatoms independently selected from the group consisting of N, O, S, Se and Si. R 4 an aliphatic bridge with a main chain having 1 to about 20 carbon atoms, an alicyclic bridge, an aromatic bridge, an arylaliphatic bridge or an arylalicyclic bridge, comprising 0 to about 3 heteroatoms independently selected from the group consisting of N, O, S, Se and Si, and X is halogen. In Formula (XX) R 30 is —C(OH)R 1 R 2 or —COOR 14 , wherein R 1 , R 2 and R 14 are independently hydrogen, an aliphatic group with a main chain having 1 to about 20 carbon atoms, an alicyclic group, an aromatic group, an arylaliphatic group or an arylalicyclic group, comprising 0 to about 3 heteroatoms independently selected from the group consisting of N, O, S, Se and Si.

  本发明涉及一种一般式（XX）的化合物，其形成以及在不对称催化中的应用。在式（XX）中，R和R31独立地为—COOR3，—R4COOR3，—R4CHO，—R4COR3，—R4CONR5R6，—R4COX，—R4OP(═O)(OH)2，—R4P(═O)(OH)2，—R4C(O)C(R3)CR5R6和—R4CO2COR3。此外，R31也可以是氢。R3、R5和R6独立地为氢，具有主链含有1至约20个碳原子的脂肪基团，脂环基团，芳香基团，芳基脂基团或芳基脂环基团，包括0至约3个从N、O、S、Se和Si组成的杂原子。R4为具有主链含有1至约20个碳原子的脂肪桥，脂环桥，芳香桥，芳基脂桥或芳基脂环桥，包括0至约3个从N、O、S、Se和Si组成的杂原子，X为卤素。在式（XX）中，R30为—C(OH)R1R2或—COOR14，其中R1、R2和R14独立地为氢，具有主链含有1至约20个碳原子的脂肪基团，脂环基团，芳香基团，芳基脂基团或芳基脂环基团，包括0至约3个从N、O、S、Se和Si组成的杂原子。
• US9206090B2
  申请人：——

  公开号：US9206090B2

  公开（公告）日：2015-12-08
• US9969739B2
  申请人：——

  公开号：US9969739B2

  公开（公告）日：2018-05-15
• [EN] NOVEL TRICYCLIC CHIRAL COMPOUNDS AND THEIR USE IN ASYMMETRIC CATALYSIS<br/>[FR] NOUVEAUX COMPOSÉS CHIRAUX TRICYCLIQUES ET LEUR UTILISATION EN CATALYSE ASYMÉTRIQUE
  申请人：UNIV NANYANG

  公开号：WO2010027334A1

  公开（公告）日：2010-03-11

  The present invention relates to a compound of general Formula Formula (XX), its formation and its use in asymmetric catalysis. In Formula (XX) R and R31 are independently -COOR3, -R4COOR3, -R4CHO, -R4COR3, -R4CONR5R6, -R4COX, -R4OP(=O)(OH)2,, -R4P(=O)(OH)2), -R4C(O)C(R3)CR5R6 and -R4CO2COR3. In addition, R31 may also be hydrogen. R3, R5 and R6 are independently hydrogen, an aliphatic group with a main chain having 1 to about 20 carbon atoms, an alicyclic group, an aromatic group, an arylaliphatic group or an arylalicyclic group, comprising 0 to about 3 heteroatoms independently selected from the group consisting of N, O, S, Se and Si. R4 an aliphatic bridge with a main chain having 1 to about 20 carbon atoms, an alicyclic bridge, an aromatic bridge, an arylaliphatic bridge or an arylalicyclic bridge, comprising 0 to about 3 heteroatoms independently selected from the group consisting of N, O, S, Se and Si, and X is halogen. In Formula (XX) R30 is -C(OH)R1R2 or -COOR14, wherein R1, R2 and R14 are independently hydrogen, an aliphatic group with a main chain having 1 to about 20 carbon atoms, an alicyclic group, an aromatic group, an arylaliphatic group or an arylalicyclic group, comprising 0 to about 3 heteroatoms independently selected from the group consisting of N, O, S, Se and Si.
• Chemzymes: A New Class of Structurally Rigid Tricyclic Amphibian Organocatalyst Inspired by Natural Product
  作者：Jian Xiao、Feng-Xia Xu、Yun-Peng Lu、Teck-Peng Loh

  DOI：10.1021/ol9029758

  日期：2010.3.19

  A new class of structurally rigid tricyclic amphibian chiral catalyst was rationally designed based on the hexahydropyrrolo[2,3-b]indole skeleton as a new type of chemzyme. This new type of chemzyme possesses a structurally rigid tricyclic skeleton and a chiral pocket which provides a well-organized chiral environment for asymmetric induction, as well as a hydrophobic pocket to enable organocatalytic

  基于六氢吡咯并[2,3- b ]吲哚骨架作为新型的化学酶，合理设计了新型结构刚性的三环两性手性催化剂。这种新型的化学酶具有结构刚性的三环骨架和手性囊，为不对称诱导提供了组织良好的手性环境，以及疏水性囊，使有机催化反应在有机溶剂和水中均能顺利进行。