methyl 4-(tert-butoxycarbonylamino)-3-oxopentanoate | 120021-34-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: methyl 4-(tert-butoxycarbonylamino)-3-oxopentanoate
• 英文别名: 4-(N-Boc-amino)-3-oxo-pentanoic Acid Methyl Ester；methyl 4-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopentanoate
• CAS: 120021-34-3
• 化学式: C₁₁H₁₉NO₅
• 分子量: 245.276
• InChiKey: HMITWDFQTIEUAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 4-(tert-butoxycarbonylamino)-3-oxopentanoate 在 羟胺 作用下， 生成 6-Amino-5-[(Z)-hydroxyimino]-heptanoic acid; hydrochloride
  参考文献：
  名称：

  The design and synthesis of inhibitors of dethiobiotin synthetase as potential herbicides

  摘要：

  Dethiobiotin synthetase (DTBS;E.C. 6.6.6.6), the penultimate enzyme in the biosynthesis of the essential vitamin biotin, is a new potential target for novel herbicides. Inhibitors were designed based on mechanistic and structural information. The in-vitro activities of these potential inhibitors versus the bacterial enzyme are reported here. Mimics of 7,8-diaminopelargonic acid (DAPA) or the DAPA carbamate reaction intermediate were substrates or partial substrates for the enzyme. Synergistic binding with ATP was noted with compounds which contained an amino functionality, NMR studies and X-ray structures confirmed that the inhibitors could be phosphorylated by the enzyme. Several series of potential inhibitors were designed to take advantage of this partial substrate activity by generating potentially more tightly bound phosphorylated inhibitors in situ, Structure-activity relationships for these series based on both substrate and inhibitory activity are described herein. An X-ray structure for one of these inhibitors is also discussed. Although considerable potential for inhibitors of this type was demonstrated, none of the compounds reported showed sufficient herbicidal activity to be a commercial proposition. (C) 1999 Society of Chemical Industry.

  DOI：

  10.1002/(sici)1096-9063(199903)55:3<236::aid-ps888>3.0.co;2-0
• 作为产物：
  描述：

  N-t-butyloxycarbonyl-DL-alanine 、 magnesium monomethyl malonate 在 N,N'-羰基二咪唑 作用下， 生成 methyl 4-(tert-butoxycarbonylamino)-3-oxopentanoate
  参考文献：
  名称：

  Baker's Yeast Reduction ofN-Protected Methyl 4-Amino-3-oxobutanoates and 3-oxopentanoates

  摘要：

  面包酵母还原 N-叔丁氧基羰基 (Boc) 或 N-苄氧基羰基 (Cbz) 保护的 4-氨基-3-氧代戊酸甲酯 4b-e 和 4-氨基-3-氧代丁酸 7a,b 立体选择性地得到赤羟基酯 5b -e和(R)-羟基酯分别为8a、b。所得N-保护的(R)-4-氨基-3-羟基丁酸甲酯(8)被转化为生物活性物质sperabillin C 1c 和(R)-GABOB [(R)4-氨基-3-羟基丁酸。 2]。

  DOI：

  10.1055/s-1992-26123

文献信息

• [EN] AMIDES AS PIM INHIBITORS<br/>[FR] AMIDES CONVENANT COMME INHIBITEURS DES PIM
  申请人：AMGEN INC

  公开号：WO2013130660A1

  公开（公告）日：2013-09-06

  The invention relates to amide-containing compounds of formula (1), and salts thereof. In some embodiments, the invention relates to inhibitors or modulators of Pim-1 and/or Pim-2, and/or Pim-3 protein kinase activity or enzyme function. In still further embodiments, the invention relates to pharmaceutical compositions comprising compounds disclosed herein, and their use in the prevention and treatment of Pim kinase related conditions and diseases, preferably cancer.

  本发明涉及式(1)的含酰胺化合物及其盐。在一些实施例中，本发明涉及Pim-1和/或Pim-2和/或Pim-3蛋白激酶活性或酶功能的抑制剂或调节剂。在更进一步的实施例中，本发明涉及包含本文披露的化合物的药物组合物，及其用于预防治疗Pim激酶相关状况和疾病，尤其是癌症的应用。
• α-Amino acid derived enaminones and their application in the synthesis of N-protected methyl 5-substituted-4-hydroxypyrrole-3-carboxylates and other heterocycles
  作者：Uroš Grošelj、Mojca Žorž、Amalija Golobič、Branko Stanovnik、Jurij Svete

  DOI：10.1016/j.tet.2013.11.008

  日期：2013.12

  simple synthesis of novel N-protected methyl 5-substituted-4-hydroxypyrrole-3-carboxylates, which exist in equilibrium with their 4-oxo tautomers, has been developed in two steps starting from N-protected α-amino acids. The key intermediates are enaminones, which can also be isolated, characterized, and used for the construction of other functionalized heterocycles, before they spontaneously decompose

  的新颖的新的和简单的合成ñ -保护的5-取代-4-羟基吡咯-3-羧酸酯，其存在于与他们的4-氧代互变异构体平衡，已经在从开始的两个步骤被开发ñ -保护的α氨基酸。关键中间体是烯胺酮，其也被分离，表征，并用于其它官能化杂环的结构，才自发分解到吡咯产物。4-羟基吡咯易于部分空中氧化，但是可以有效地烷基化或还原成稳定的多取代的吡咯烷衍生物。
• Construction of Vicinal Tetrasubstituted Stereogenic Centers<i>via</i>a Mannich-Type Organocatalyzed Addition of Δ²-Pyrrolin-4-ones to Isatin Imines
  作者：Sebastijan Ričko、Anže Meden、Luka Ciber、Bogdan Štefane、Franc Požgan、Jurij Svete、Uroš Grošelj

  DOI：10.1002/adsc.201701384

  日期：2018.3.20

  Mannich‐type addition to isatin‐derived ketimines to furnish the non‐racemic oxindole‐Δ2‐pyrrolin‐4‐one adducts, stereoselectively (up to 96% ee, dr≥15:1). The oxindole–pyrrolone products feature vicinal tetrasubstituted carbon stereocenters. The developed protocol has a broad substrate scope and tolerates diverse substituents at position C‐5 in 4‐pyrrolones and at positions N‐1 and C‐5/7 in isatin imines

  外消旋Δ 2 -吡咯啉-4-酮（即4-吡咯酮类）中，从两个步骤容易获得ñ -保护的α -氨基酸，离岗organocatalysed不对称曼尼希型除靛红衍生的酮亚胺，得到非外消旋的羟吲哚-Δ 2 -吡咯啉-4-酮加合物，立体选择性（高达96％ee值，博士≥15：1）。羟吲哚-吡咯烷酮产品具有邻近的四取代碳立体中心。所开发的方案具有广泛的底物范围，并且可以耐受4-吡咯烷酮中C-5位置以及异亚胺中N-1和C-5 / 7位置的各种取代基。
• [EN] DIHYDROPYRROLOPYRIDINE INHIBITORS OF ROR-GAMMA<br/>[FR] INHIBITEURS DE ROR-GAMMA À BASE DE DIHYDROPYRROLOPYRIDINE
  申请人：VITAE PHARMACEUTICALS INC

  公开号：WO2016061160A1

  公开（公告）日：2016-04-21

  Provided are novel compounds of Formula (I): pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof, which are useful in the treatment of diseases and disorders mediated by RORy. Also provided are pharmaceutical compositions comprising the novel compounds of Formula (I) and methods for their use in treating one or more inflammatory, metabolic, autoimmune and other diseases or disorders.

  提供了式（I）的新化合物：其药用盐以及药物组合物，可用于治疗由RORγ介导的疾病和紊乱。还提供了包含式（I）的新化合物的药物组合物，以及它们在治疗一种或多种炎症性、代谢性、自身免疫和其他疾病或紊乱中的使用方法。
• Organocatalyzed Deracemization of Δ²-Pyrrolin-4-ones
  作者：Sebastijan Ričko、Anže Meden、Anže Ivančič、Andrej Perdih、Bogdan Štefane、Jurij Svete、Uroš Grošelj

  DOI：10.1002/adsc.201700539

  日期：2017.7.3

  Racemic pyrrolin-4-ones, accessible from α-amino acids, undergo asymmetric stereoselective organocatalyzed 1,4-additions to trans-β-nitrostyrenes (up to 98 % ee; dr up to 97:3). From a series of typical organocatalysts, the best performance was achieved using (+)-camphor-1,3-diamine-derived bifunctional organocatalysts. A broad substrate scope and some follow-up modifications have been demonstrated

  可从α-氨基酸获得的外消旋吡咯啉4- one经过不对称的立体选择性有机催化1,4-加成反式-β-硝基苯乙烯（ee高达98％；dr高达97：3）。在一系列典型的有机催化剂中，使用（+）-樟脑-1,3-二胺衍生的双官能有机催化剂可实现最佳性能。已经证明了广泛的基材范围和一些后续的修改。