methyl (S)-2',3',4',9'-tetrahydrospiro[cyclopentane-1,1'-pyrido[3,4-b]indole]-3'-carboxylate

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: methyl (S)-2',3',4',9'-tetrahydrospiro[cyclopentane-1,1'-pyrido[3,4-b]indole]-3'-carboxylate
• 英文别名: methyl (3S)-spiro[2,3,4,9-tetrahydropyrido[3,4-b]indole-1,1'-cyclopentane]-3-carboxylate
• 化学式: C₁₇H₂₀N₂O₂
• 分子量: 284.358
• InChiKey: SFOHSSOTLWYBOJ-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  54.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  Fmoc-L-色氨酸 、 环戊酮 生成 methyl (S)-2',3',4',9'-tetrahydrospiro[cyclopentane-1,1'-pyrido[3,4-b]indole]-3'-carboxylate
  参考文献：
  名称：

  Liquid-phase parallel synthesis of tetrahydro-β-carbolines

  摘要：

  Parallel synthesis of beta-carbolines on soluble polyethylene glycol (PEG-OH) support is demonstrated. One-pot condensation of polymer-bound tryptophan residues with various aldehydes and ketones has been carried out in the presence of p-TSA as a catalyst to deliver immobilized 1,2,3,4-tetrahydro-beta-carbolines. Subsequent disengagement of the appendant from the polymer support afforded the desired products in good yield and acceptable purity. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01100-6

文献信息

• Two‐in‐One Strategy for Palladium‐Catalyzed C−H Functionalization in Water
  作者：Huiying Zeng、Zemin Wang、Chao‐Jun Li

  DOI：10.1002/anie.201813391

  日期：2019.2.25

  Transition metal catalyzed C−H functionalizations have been developed as powerful methods for C−C bond formations. Directing groups, removable directing groups, traceless directing groups, and transient directing groups (TDGs) have been successfully used to improve the reaction efficiencies. For the development of greener and more sustainable methods, C−H functionalization using a TDG that also serves

  过渡金属催化的CH官能化已被开发为形成CC键的有力方法。导向基团，可移动的导向基团，无痕导向基团和瞬态导向基团（TDG）已被成功地用于提高反应效率。为了开发更绿色，更可持续的方法，研究了使用TDG的CH功能化，该TDG还可以用作水性溶剂中的试剂。使用酮在水中的钯催化的色胺类胺的CH-H官能化成功生成了四氢-β-咔啉，其四级碳中心位于C1。讨论了氘标记实验以提供对该机理的深入了解。吡啶的C2位也通过该策略成功地官能化。
• Parallel Synthesis of 1,2,3,4-Tetrahydro-β-carbolines Using Microwave Irradiation
  作者：Chung-Ming Sun、Cheng-Yi Wu

  DOI：10.1055/s-2002-34220

  日期：——

  Novel soluble polymer supported synthesis of 1,2,3,4-tetrahydro-β-carboline derivatives in the microwave oven is reported. Commercially available Fmoc-protected tryptophan was directly anchored to MeO-PEG-OH via an ester linkage in the presence of DCC and DMAP. One pot cyclocondensation of polymer-bound tryptophan with a variety of aldehydes and ketones has been carried out under microwave irradiation to provide immobilized 1,2,3,4-tetra-hydro-β-carboline derivatives. The desired products were then liberated from the soluble matrix in good yield and good purity.

  报告了在微波炉中合成 1,2,3,4-四氢-δ-咔啉衍生物的新型可溶性聚合物。在 DCC 和 DMAP 的存在下，市售的 Fmoc 保护色氨酸通过酯键直接锚定到 MeO-PEG-OH 上。在微波辐照下，将聚合物结合的色氨酸与各种醛和酮进行一锅环缩合，从而得到固定的 1,2,3,4-四氢δ-咔啉衍生物。随后，所需的产物以良好的收率和纯度从可溶性基质中释放出来。
• Liquid-phase parallel synthesis of tetrahydro-β-carbolines
  作者：Wen-Ben Yeh、Mei-Jung Lin、Chung-Ming Sun

  DOI：10.1016/s0040-4039(03)01100-6

  日期：2003.6

  Parallel synthesis of beta-carbolines on soluble polyethylene glycol (PEG-OH) support is demonstrated. One-pot condensation of polymer-bound tryptophan residues with various aldehydes and ketones has been carried out in the presence of p-TSA as a catalyst to deliver immobilized 1,2,3,4-tetrahydro-beta-carbolines. Subsequent disengagement of the appendant from the polymer support afforded the desired products in good yield and acceptable purity. (C) 2003 Elsevier Science Ltd. All rights reserved.