(S)-2-isocyano-4-methylpentanoate | 158340-98-8

• 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: (S)-2-isocyano-4-methylpentanoate
• 英文别名: methyl 2-isobutyl-α-isocyanoacetate；methyl 2-isocyano-4-methylpentanoate；(2S)-2-Isocyano-4-methylpentanoic acid methyl ester；methyl (2S)-2-isocyano-4-methylpentanoate
• CAS: 158340-98-8
• 化学式: C₈H₁₃NO₂
• 分子量: 155.197
• InChiKey: ZWTPUHSQAWCFFP-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-isocyano-4-methylpentanoate 在 盐酸 、 lithium hydroxide 、 二苯基磷酸 、 碳酸氢钠 、 二乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、310.26 kPa 条件下， 反应 300.0h， 生成 (3S,7S,10S)-10-Amino-6-hydroxy-3-isobutyl-7-methyl-1,4,8-triaza-cyclotridecane-2,5,9-trione
  参考文献：
  名称：

  Concise total synthesis of the prolyl endopeptidase inhibitor eurystatin A via a novel Passerini reaction–deprotection–acyl migration strategy

  摘要：

  The Passerini reaction between suitably protected alaninal, leucine isonitrile, and ornithine components delivered adducts 10a,b in high yield. Orthogonal N-deprotection of 10a led, via a smooth O- to N-acyl migration, to 11, which constitutes the entire skeleton of the eurystatins. Subsequent deprotection, macrocyclization, elaboration, and final oxidation steps efficiently afforded eurystatin A 1a in high overall yield. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01287-4
• 作为产物：
  描述：

  (S)-methyl 2-formamido-4-methylpentanoate 在 N-甲基吗啉 、 三光气 作用下， 以 二氯甲烷 为溶剂， 反应 2.17h， 以80%的产率得到(S)-2-isocyano-4-methylpentanoate
  参考文献：
  名称：

  Investigation of the Configurational Stabilities of Chiral Isocyanoacetates in Multicomponent Reactions

  摘要：

  Isocyanoacetates are uniquely reactive compounds characterized by an ambivalent isocyano functional group and an enolizable alpha-carbon. It is widely believed that chiral alpha-substituted isocyanoacetates are configurationally unstable in some synthetically useful isocyanide-based multicomponent reactions. Herein, we demonstrate that chiral isocyanoacetates can be used with minimal to negligible epimerization in a variety of canonical Ugi four-component condensations as well as Joullie-Ugi three-component condensations, reactions that are particularly useful for constructing complex peptide structures in a single synthetic operation.

  DOI：

  10.1021/jo201817k

文献信息

• An efficient metal-free synthesis of carbodiimide-tethered amino acid conjugates
  作者：Srinivasulu Chinthaginjala、Divya Kuppi Reddy Gari、Sagar Nagamangala Ramachandra、Vommina V. Sureshbabu

  DOI：10.1080/00397911.2020.1769132

  日期：2020.7.17

  straightforward oxidative cross-coupling synthesis of carbodiimide tethered amino acid conjugates from amino acid-derived isocyanides and aryl amines mediated by I2/tert-butyl hydroperoxide. Using this protocol, the title compounds were obtained in good isolated yields. This protocol is of short reaction duration, base-free, racemization free and avoids the necessity of transition metal catalysts. Graphical Abstract

  摘要 在这项研究中，我们报道了由氨基酸衍生的异氰化物和芳胺在 I2/叔丁基氢过氧化物介导下直接氧化交叉偶联合成碳二亚胺系链氨基酸偶联物。使用该方案，以良好的分离产率获得了标题化合物。该协议反应时间短，无碱，无外消旋化，避免了过渡金属催化剂的必要性。图形概要
• Synthesis of Highly Substituted Imidazole Uracil Containing Molecules via Ugi-4CR and Passerini-3CR
  作者：Rudrakshula Madhavachary、Tryfon Zarganes-Tzitzikas、Pravin Patil、Katarzyna Kurpiewska、Justyna Kalinowska-Tłuścik、Alexander Dömling

  DOI：10.1021/acscombsci.7b00145

  日期：2018.4.9

  The synthesis of uracil/thymine containing tetra/trisubstituted imidazole derivatives was demonstrated using Ugi/Passerini-reaction followed by a postcyclization reaction sequence. The approach enables the one-pot facile construction of diverse compounds in moderate to excellent yields (47–82%). The 5-fluorouracil and 5-methyluracil moieties afford potentially bioactive molecules with drug-like properties

  含有尿嘧啶/胸腺嘧啶的四/三取代的咪唑衍生物的合成已通过Ugi / Passerini反应和随后的环化反应序列进行了证明。该方法使一锅多用的化合物能够以中等到出色的产率（47-82％）轻松构建。5-氟尿嘧啶和5-甲基尿嘧啶部分提供具有类似药物性质的潜在生物活性分子。这些脚手架目前正在欧洲铅工厂的筛选平台中使用。
• The synthesis of eurystatin A
  作者：Ulrich Schmidt、Steffen Weinbrenner

  DOI：10.1039/c39940001003

  日期：——

  Eurystatin A, a new prolyl endopeptidase inhibitor isolated from Streptomyces eurythermus has now been synthesized.

  现已合成了一种新的脯氨酰内肽酶抑制剂 Eurystatin A，它是从欧氏链霉菌（Streptomyces eurythermus）中分离出来的。
• Efficient and Regiospecific Syntheses of Peptides with Piperazic and Dehydropiperazic Acids via a Multicomponent Reaction
  作者：Emma L. Handy、Kyle A. Totaro、Charlie P. Lin、Jason K. Sello

  DOI：10.1021/ol501425b

  日期：2014.7.3

  Peptides containing N2-acyl piperazic or 1,6-dehydropiperazic acids can be formed efficiently via a novel multicomponent reaction of 1,4,5,6-tetrahydropyridazines, isocyanides, and carboxylic acids. Remarkably, the reaction's induced intramolecularity can enable the regiospecific formation of products with N2-acyl piperazic acid, which counters the intrinsic and troublesome propensity for piperazic acids to react at N1 in acylations. The utility of the methodology is demonstrated in the synthesis of the bicyclic core of the interleukin-1β converting enzyme inhibitor, Pralnacasan.
• Weygand,F. et al., Angewandte Chemie, 1966, vol. 78, p. 640
  作者：Weygand,F. et al.

  DOI：——

  日期：——