(1S,3S,1'S)-1-[1'-[(N-benzyloxycarbonyl)amino]-3'-methyl-butyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester | 1009587-37-4

• 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: (1S,3S,1'S)-1-[1'-[(N-benzyloxycarbonyl)amino]-3'-methyl-butyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester
• 英文别名: methyl (1S,3S)-1-[(1S)-3-methyl-1-(phenylmethoxycarbonylamino)butyl]-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
• CAS: 1009587-37-4
• 化学式: C₂₆H₃₁N₃O₄
• 分子量: 449.55
• InChiKey: RIDRJTMSIOYEGO-FIXSFTCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  92.4
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  L-色氨酸甲酯盐酸盐 在 碳酸氢钠 、 三氟乙酸 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 0.5h， 生成 (1R,3S,1'S)-1-[1'-[(N-benzyloxycarbonyl)amino]-3'-methyl-butyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester 、 (1S,3S,1'S)-1-[1'-[(N-benzyloxycarbonyl)amino]-3'-methyl-butyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester
  参考文献：
  名称：

  肽和肽醛作为Pictet-Spengler反应的底物。

  摘要：

  Pictet-Spengler（PS）反应是用各种类型的底物进行的：H-Trp-OMe和二肽，N-末端Trp为芳基乙胺组分，Z保护的氨基醛和肽醛为羰基组分。我们发现，Trp衍生物的C末端部分对反应的立体选择性没有任何影响，对于Trp和二肽的简单酯，其结果相同。

  DOI：

  10.1002/psc.2516

文献信息

• Influence of reaction conditions on products of the Pictet–Spengler condensation
  作者：Karolina Pulka、Aleksandra Misicka

  DOI：10.1016/j.tet.2011.01.018

  日期：2011.3

  The Pictet–Spengler reaction with N-protected α-amino aldehydes was found to be very sensitive to reaction conditions. The outcome of the reaction can be controlled mainly by choice of solvent. Tetrahydro-β-carbolines were obtained in apolar solvents, while in polar media octahydro-bipyrroloindoles were the main compounds. Temperature, amount of acid and reaction time also influenced the final results

  发现具有N保护的α-氨基醛的Pictet-Spengler反应对反应条件非常敏感。反应的结果主要可以通过选择溶剂来控制。四氢-β-咔啉是在非极性溶剂中获得的，而在极性介质中八氢-双吡咯并吲哚是主要的化合物。温度，酸的量和反应时间也影响PS反应的最终结果。根据条件，形成具有副构型中心的相反构型的产物，其是氨基醛衍生的副产物。
• Diastereoselective Pictet–Spengler condensation of tryptophan with α-amino aldehydes as chiral carbonyl components
  作者：Karolina Pulka、Piotr Kulis、Dagmara Tymecka、Lukasz Frankiewicz、Marcin Wilczek、Wiktor Kozminski、Aleksandra Misicka

  DOI：10.1016/j.tet.2007.11.037

  日期：2008.2

  The Pictet-Spengler reaction of Trp with alpha-amino aldehydes derived from L and D-amino acids was studied in terms of double stereodifferentiation. The results observed for D-amino aldehydes represent 'matched' situation (one diastereoisomer was formed) whereas with L-amino aldehydes 'mismatched' (two diastereoisomers were formed). The conformation of newly formed six-membered ring was analyzed. It was found that stable conformers were different for cis and trans isomers. (c) 2007 Elsevier Ltd. All rights reserved.
• Peptides and peptidoaldehydes as substrates for the Pictet-Spengler reaction
  作者：Karolina Pulka、Marta Slupska、Anna Puszko、Maria Misiak、Marcin Wilczek、Wiktor Kozminski、Aleksandra Misicka

  DOI：10.1002/psc.2516

  日期：2013.7

  The Pictet–Spengler (PS) reaction was performed with various types of substrates: H‐Trp‐OMe and dipeptides with N‐terminal Trp as arylethylamine components and Z‐protected amino aldehydes and peptidoaldehydes as carbonyl components. We found that the C‐terminal part of Trp derivatives did not have any influence on the stereoselectivity of the reaction and the results are the same for simple esters

  Pictet-Spengler（PS）反应是用各种类型的底物进行的：H-Trp-OMe和二肽，N-末端Trp为芳基乙胺组分，Z保护的氨基醛和肽醛为羰基组分。我们发现，Trp衍生物的C末端部分对反应的立体选择性没有任何影响，对于Trp和二肽的简单酯，其结果相同。