Boc-L-Pro-indoline | 198218-53-0

• 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: Boc-L-Pro-indoline
• 英文别名: tert-butyl (2S)-2-(2,3-dihydroindole-1-carbonyl)pyrrolidine-1-carboxylate
• CAS: 198218-53-0
• 化学式: C₁₈H₂₄N₂O₃
• 分子量: 316.4
• InChiKey: MUFZLOBFHJPNMP-HNNXBMFYSA-N

物化性质

• 沸点：
  497.6±45.0 °C(Predicted)
• 密度：
  1.199±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Boc-L-Pro-indoline 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以62%的产率得到(S)-1-prolylindoline
  参考文献：
  名称：

  借氢对α-氨基酯和酰胺进行N-烷基化

  摘要：

  开发了一种使用醇进行铱催化的氨基酯和酰胺直接烷基化的方法，该方法可以利用胺的游离碱和 HCl 盐。该反应通过借氢机制进行。

  DOI：

  10.1002/ejoc.202200152
• 作为产物：
  描述：

  吲哚啉 、 BOC-L-脯氨酸 在 吡啶 作用下， 以 乙酸乙酯 为溶剂， 反应 16.0h， 以84%的产率得到Boc-L-Pro-indoline
  参考文献：
  名称：

  借氢对α-氨基酯和酰胺进行N-烷基化

  摘要：

  开发了一种使用醇进行铱催化的氨基酯和酰胺直接烷基化的方法，该方法可以利用胺的游离碱和 HCl 盐。该反应通过借氢机制进行。

  DOI：

  10.1002/ejoc.202200152

文献信息

• Tunable and Cooperative Catalysis for Enantioselective Pictet‐Spengler Reaction with Varied Nitrogen‐Containing Heterocyclic Carboxaldehydes
  作者：Yuk‐Cheung Chan、Marcus H. Sak、Scott A. Frank、Scott J. Miller

  DOI：10.1002/anie.202109694

  日期：2021.11.8

  We utilize diverse N-heterocyclic carboxaldehyde and regioisomers in Pictet-Spengler reaction. Compatibility was enabled by fine tuning the achiral carboxylic acid co-catalyst in the presence of chiral peptidic squaramide. Synthetic utility was demonstrated by stereoselective synthesis of pyridine-containing analogues of medicinally related molecules, including U.S. FDA approved drug Tadalafil.

  我们在 Pictet-Spengler 反应中利用多种N-杂环甲醛和区域异构体。通过在手性肽方酰胺存在下微调非手性羧酸助催化剂来实现兼容性。通过立体选择性合成医学相关分子的含吡啶类似物（包括美国 FDA 批准的药物他达拉非）证明了合成效用。
• Stereoselective synthesis of E-64 and related cysteine proteases inhibitors from 2,3-epoxyamides
  作者：Francisco Sarabia、Antonio Sánchez-Ruiz、Samy Chammaa

  DOI：10.1016/j.bmc.2004.12.018

  日期：2005.3.1

  The stereoselective synthesis of cathepsin inhibitors from indoline type epoxyamides is described. The use of this type of epoxyamides permitted the preparation of E-64 and CA-074 related compounds depending on the order in which the key steps, the oxidation of indoline amides to indole amides and oxidative acetal cleavage were undertaken. By taking advantage of the facile substitution of the indole of the corresponding indole epoxyamides, with various nucleophiles, we were able to prepare different epoxysuccinic acids derivatives as potential cathepsin inhibitors. (C) 2004 Elsevier Ltd. All rights reserved.
• Chiral Lewis Acid Controlled Synthesis (CLAC Synthesis): Chiral Lewis Acids Influence the Reaction Course in Asymmetric Aldol Reactions for the Synthesis of Enantiomeric Dihydroxythioester Derivatives in the Presence of Chiral Diamines Derived from L-Proline
  作者：Shū Kobayashi、Mineko Horibe

  DOI：10.1002/chem.19970030914

  日期：1997.9

  AbstractBoth enantiomers of 2,3‐dihy‐droxythioester derivatives were prepared with almost perfect stereochemical control by chiral Lewis acid controlled synthesis (CLAC synthesis). CLAC synthesis means synthesis of all individual diastereomers or enantiomers from the same starting materials by designing chiral Lewis acids. For example, (Z)‐1‐ethyl‐thio‐1‐(trimethylsiloxy)‐2‐(tert‐butyldi‐methylsiloxy)ethene (1) reacted with aldehydes in the presence of chiral tin(II) Lewis acids using (S)‐1‐methyl‐2‐[(isoin‐dolinyl)methyl]pyrrolidine (4) and (S)‐1‐methyl‐2‐[(indolinyl)methyl]pyrrolidine (5) to afford enantiomeric dihydroxy‐thioester derivatives. Chiral diamines 4 and 5, which were readily prepared from L‐proline, differ only in the fusion point of the benzene ring connected to the pyrrolidine moiety. The unique selectivities were ascribed to the conformational difference between the chiral tin(II) Lewis acids of chiral diamines 4 and 5, and the function of chiral sources for obtaining high selectivities has also been clarified.
• CYANOPYRROLIDINES AS DUB INHIBITORS FOR THE TREATMENT OF CANCER
  申请人：MISSION THERAPEUTICS LIMITED

  公开号：US20180194724A1

  公开（公告）日：2018-07-12

  The present invention relates to novel compounds and method for the manufacture of inhibitors of deubiquitylating enzymes (DUBs). In particular, the invention relates to the inhibition of ubiquitin C-terminal hydrolase L1 (UCHL1) and ubiquitin C-terminal hydrolase 30 or ubiquitin specific peptidase 30 (USP30). The invention further relates to the use of DUB inhibitors in the treatment of cancer and conditions involving mitochondrial dysfunction. Compounds of the invention include compounds having the formula (I) or a pharmaceutically acceptable salt thereof, wherein R 1 ,R 2 ,R 3 ,R 4 ,R 5 ,R 6 ,R 7 ,R 8 and R 9 are as defined herein.
• <i>N</i> ‐Alkylation of α‐Amino Esters and Amides through Hydrogen Borrowing
  作者：Charlotte E. Coomber、Louis J. Diorazio

  DOI：10.1002/ejoc.202200152

  日期：2022.8.26

  A method for the iridium catalysed direct alkylation of amino esters and amides using alcohols, which can utilise both the free base and HCl salts of the amine, was developed. This reaction proceeds through a borrowing hydrogen borrowing mechanism.

  开发了一种使用醇进行铱催化的氨基酯和酰胺直接烷基化的方法，该方法可以利用胺的游离碱和 HCl 盐。该反应通过借氢机制进行。