methyl 4-[(tert-butoxycarbonyl)amino]-3-oxobutanoate | 119960-04-2

• 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-butoxycarbonyl)amino]-3-oxobutanoate
• 英文别名: 4-(Boc-amino)-3-oxobutanoic acid Methyl ester；methyl 4-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxobutanoate
• CAS: 119960-04-2
• 化学式: C₁₀H₁₇NO₅
• 分子量: 231.249
• InChiKey: WOBLFZAAUVEUJC-UHFFFAOYSA-N

物化性质

• 沸点：
  325.3±22.0 °C(Predicted)
• 密度：
  1.119±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 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-butoxycarbonyl)amino]-3-oxobutanoate 在 platinum on activated charcoal 吡啶 、 sodium hydroxide 、 磷酸 、 盐酸羟胺 、 氢气 、 phosphorus pentoxide 、 碳酸氢钠 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醇 、 水 为溶剂， 反应 44.0h， 生成 (4R,6R)-4-benzyloxycarbonylamino-6-(tert-butoxycarbonylamino)methyl-3,4,5,6-tetrahydro-2H-pyran-2-one
  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
• 作为产物：
  描述：

  BOC-甘氨酸 在 magnesium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 22.0h， 生成 methyl 4-[(tert-butoxycarbonyl)amino]-3-oxobutanoate
  参考文献：
  名称：

  新型3D丰富的α-氨基酸衍生的3-吡唑烷酮的合成

  摘要：

  研究了在位置N（1）和/或C（5）上官能化的新型3-吡唑烷酮衍生物的合成方法。由N-保护的甘氨酸通过Masamune-Claisen同源化，还原，O-甲磺酰化和与肼衍生物的环化反应，在四个步骤中制备5-氨基烷基-3-吡唑烷酮。通过酸解脱保护制备游离胺。还通过用水合肼对N-Boc-吡咯啉-2（5H）-1进行“环切换”转化来制备标题化合物。对5-（N-烷基-N-Cbz-氨基甲基）吡唑烷-3-酮进行氢解脱保护，然后与1,1'-羰基二咪唑（CDI）环合，得到两个新的全氢咪唑并[1,5-b]吡唑代表，是几乎未开发的杂环系统。3-氧代吡唑烷-5-羧酸的酰胺化以中等收率得到相应的羧酰胺。由（S）-AlaOMe和（S）-ProOMe获得的非对映体非外消旋羧酰胺通过MPLC分离。

  DOI：

  10.17344/acsi.2017.3438

文献信息

• 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。
• 一种制备盐酸氨基乙酰丙酸的方法
  申请人：爱斯特（成都）生物制药股份有限公司

  公开号：CN108440319B

  公开（公告）日：2021-05-18

  本发明公开了一种制备盐酸氨基乙酰丙酸的方法,属于化学合成领域。本发明以甘氨酸衍生物为起始原料，通过缩合、取代、脱保护和水解四步反应，提供了一条全新的盐酸氨基乙酰丙酸合成路线，此合成方法路线短，操作简单且收率高，适于大规模工业化生产。
• The design and synthesis of inhibitors of dethiobiotin synthetase as potential herbicides
  作者：Alan R Rendina、Wendy S Taylor、Katharine Gibson、George Lorimer、Dennis Rayner、Bruce Lockett、Kevin Kranis、Barry Wexler、Dana Marcovici-Mizrahi、Ayelet Nudelman、Abraham Nudelman、Eileen Marsilii、Hongji Chi、Zdislaw Wawrzak、Joseph Calabrese、Weijun Huang、Jia Jia、Gunter Schneider、Ylva Lindqvist、Guang Yang

  DOI：10.1002/(sici)1096-9063(199903)55:3<236::aid-ps888>3.0.co;2-0

  日期：1999.3

  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.
• Inhibitors of biotin biosynthesis as potential herbicides
  作者：Ayelet Nudelman、Dana Marcovici-Mizrahi、Abraham Nudelman、Dennis Flint、Vernon Wittenbach

  DOI：10.1016/j.tet.2003.12.047

  日期：2004.2

  Isosteric derivatives and analogues of the 7-keto-8-aminopelargonic acid (KAPA), 7,8-diaminopelargonic acid (DAPA) and desthiobiotin (DTB) vitamer intermediates involved in the biosynthetic pathway of biotin were prepared and evaluated as potential herbicides. The most active compound was desmethyl-KAPA which displayed a GR(50) (concentration of the active compound that causes a 50% growth inhibition) value of 8 ppm, where values <50 ppm are considered herbicidal. Other KAPA analogs where the terminal Me group was replaced by bulkier substituents such as Et, i-Pr and HOCH2 showed moderate activity. (C) 2003 Elsevier Ltd. All rights reserved.
• Chain extension of amino acid skeletons: preparation of ketomethylene isosteres
  作者：Cory R Theberge、Charles K Zercher

  DOI：10.1016/s0040-4020(03)00052-8

  日期：2003.2

  Ketomethylene isosteric replacements for peptide bonds were generated through a zinc carbenoid-mediated chain extension reaction in which a variety of amino acid-derived beta-keto esters are converted to gamma-keto esters in a single step. The reaction tolerates a variety of protecting groups and amino acid side chains with no epimerization of the amino acid stereocenter. (C) 2003 Elsevier Science Ltd. All rights reserved.