2-(carbobenzyloxy)amino-4-butyrolactone | 31332-88-4

• 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: 2-(carbobenzyloxy)amino-4-butyrolactone
• 英文别名: (3RS)-2-Oxo-3-[N-(benzyloxycarbonyl)amino]tetrahydrofuran；benzyloxycarbonyl homoserine lactone；(S)-3-(N-benzyloxycarbonylamino)tetrahydrofuran-2-one；α-(N-carbobenzoxyamino)-γ-butyrolactone；(2-oxo-tetrahydro-furan-3-yl)-carbamic acid benzyl ester；N-benzyloxycarbonyl-DL-homoserine lactone；N-Benzyloxycarbonyl-DL-homoserin-lacton；benzyl N-(2-oxooxolan-3-yl)carbamate
• CAS: 31332-88-4
• 化学式: C₁₂H₁₃NO₄
• mdl: MFCD03548315
• 分子量: 235.24
• InChiKey: FKWDZIFOVOUDAG-UHFFFAOYSA-N

物化性质

• 熔点：
  105-188 °C
• 沸点：
  466.1±44.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)
• 保留指数：
  2099.5

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(carbobenzyloxy)amino-4-butyrolactone 在 selenium 、 lithium hydroxide monohydrate 、 lithium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 N-Carbobenzoxy-DL-selenomethionin
  参考文献：
  名称：

  一种采用一锅法合成硒代蛋氨酸的方法

  摘要：

  本发明公开了一种采用一锅法合成硒代蛋氨酸的方法，包括步骤为：将硒和还原剂混合发生还原反应，得到金属二氧化物M­2Se2；将α‑胺基保护的高丝氨酸内酯加入到还原反应结束后的含有金属二氧化物M­2Se2的溶液中反应，得到α‑胺基保护的二硒代高胱氨酸；对α‑氨基保护的二硒代高胱氨酸先进行还原，再甲基化，得到α‑胺基保护的硒代蛋氨酸；对α‑胺基保护的硒代蛋氨酸去保护得到硒代蛋氨酸。通过上述方式，本发明的合成方法成本低，产率高，产品纯度高，可用于大批量生产，避免了工艺环节中可能会产生的毒性污染，极大减少了对环境的污染和对操作人员的伤害。

  公开号：

  CN108794365B
• 作为产物：
  描述：

  α-溴-γ-丁内酯 在 ammonium hydroxide 作用下， 生成 2-(carbobenzyloxy)amino-4-butyrolactone
  参考文献：
  名称：

  324.用于合成具有功能性γ-取代基的α-氨基丁酸衍生物的中间体的改进制备

  摘要：

  DOI：

  10.1039/jr9580001629

文献信息

• Synthesis and in vitro enzyme activity of aza, oxa and thia derivatives of bacterial cell wall biosynthesis intermediates†
  作者：Russell J. Cox、Paul S. H. Wang

  DOI：10.1039/b105117m

  日期：——

  Mechanism based inhibitors of diaminopimelate aminotransferase (DAP-AT) were designed using knowledge of its substrate specificity and mechanism. Synthesis of thiolester and amide substrate analogues was achieved prior to in vitro inhibition studies, but ester analogues proved too unstable to isolate. Thia substrate analogues showed no inhibitory properties, but the aza substrate analogue 12a showed reversible inhibition vs. DAP-AT and time dependent inhibition in the absence of the natural substrate 4. Substrate analogue 12a is the first example of an amide inhibitor of PLP dependent enzymes. Antibiotic properties of 12a were also briefly assessed.

  基于对二氨基庚二酸转氨酶（DAP-AT）的底物特异性及作用机制的了解，设计了机制型抑制剂。在体外抑制实验之前，成功合成了硫酯及酰胺类底物类似物，但酯类类似物过于不稳定，无法分离。硫类底物类似物未表现出抑制作用，但氮类底物类似物12a对DAP-AT显示出可逆抑制性，并且在缺乏天然底物4的情况下显示出时间依赖性抑制作用。底物类似物12a是首个PLP依赖性酶的酰胺类抑制剂示例。同时，也对12a的抗菌特性进行了简要评估。
• Novel synthesis of [1-11C]?-vinyl-?-aminobutyric acid ([1-11C]GVG) for pharmacokinetic studies of addiction treatment
  作者：Zongren Zhang、Yu-Shin Ding、Andrei R. Studenov、Madina R. Gerasimov、Richard A. Ferrieri

  DOI：10.1002/jlcr.544

  日期：2002.3.15

  γ-Vinyl-γ-aminobutyric acid (GVG, Vigabatrin®), a suicide inhibitor of GABA-transaminase (GABA-T), has been suggested as a new drug for the treatment of substance abuse. In order to better understand its pharmacokinetics and potential side effects, we have developed a radiosynthesis of carbon-11 (t1/2=20 min) labeled GVG for positron emission tomographic (PET) studies. We report here a novel synthetic strategy to prepare the precursor and to efficiently label GVG with C-11. 5-Bromo-3-(carbobenzyloxy)amino-1-pentene was synthesized in five steps from homoserine lactone, including reduction and methylenation. This was used in a one-pot, two-step radiosynthesis. Displacement of bromide with no-carrier-added [11C]cyanide followed by acid hydrolysis afforded [1-11C]GVG with decay corrected radiochemical yields of 27±9% (n=6, not optimized) with respect to [11C]cyanide in a synthesis time of 45 min. Copyright © 2002 John Wiley & Sons, Ltd.

  γ-乙烯基-γ-氨基丁酸（GVG，维加巴林®）是一种伪自杀抑制剂，作用于GABA转氨酶（GABA-T），被建议作为治疗物质滥用的新药。为了更好地理解其药代动力学和潜在副作用，我们开发了一种碳-11（半衰期=20分钟）标记的GVG的放射合成方法，用于正电子发射断层扫描（PET）研究。我们在此报告了一种新颖的合成策略，以制备前驱体并高效标记GVG。5-溴-3-（羧苄氧基）氨基-1-戊烯是在五个步骤内从同源氨基酸内酯合成而来的，包括还原和亚甲基化。该化合物被用于一锅两步的放射合成。通过无载体添加的[11C]氰化物取代溴化物，随后进行酸性水解，得到[1-11C]GVG，经过衰变修正的放射化学产率为27±9%（n=6，未优化），合成时间为45分钟。版权所有 © 2002 John Wiley & Sons, Ltd.
• Synthesis of<scp>D,L</scp>-γ-hydroxyphosphinothricin, a potent new inhibitor of glutamine synthetase
  作者：Daniel M. Walker、John F. McDonald、Eugene W. Logusch

  DOI：10.1039/c39870001710

  日期：——

  A flexible synthesis of D,L-γ-hydroxyphosphinothricin (GHPPT), a potent inhibitor of the enzyme glutamine synthetase, is described which features silicon-mediated addition of ethyl methylphosphinate to benzyl 2-benzyloxy-carbonylamino-4-oxobutyrate; selective deprotections yield the title compound and various derivatives.

  描述了一种强力的谷氨酰胺合成酶抑制剂D，L -γ-羟基膦丝菌素（GHPPT）的柔性合成，其特征是硅介导将甲基次膦酸乙酯加到2-苄氧基-羰基氨基-4-氧代丁酸苄酯中。选择性脱保护得到标题化合物和各种衍生物。
• New synthetic routes to α-amino acids and γ-oxygenated α-amino acids. Reductive denitration and oxidative transformations of γ-nitro-α-amino acids
  作者：Maxwell J. Crossley、Yik M. Fung、Efstathia Kyriakopoulos、Jeffrey J. Potter

  DOI：10.1039/a707067e

  日期：——

  Transformation of γ-nitro-α-amino acid derivatives into α-amino acids by reductive denitration, into the γ-oxo-α-amino acids by ozonolysis of the corresponding amino acid ester nitronate derivatives, and into γ-hydroxy-α-amino acid derivatives by subsequent reduction of the oxo functionality, can be achieved in good yields. As the γ-nitro-α-amino acid derivatives are prepared from N,O-protected dehydroalanines derivable from the corresponding alanine, serine and cysteine derivatives by specific routes, the overall procedures provide a means for selective conversion of these simple α-amino acids into more complex ones.

  通过还原去硝化，γ-硝基-α-氨基酸衍生物可以转化为α-氨基酸；通过对应氨基酸酯硝酸盐衍生物的臭氧解聚，可以转化为γ-氧-α-氨基酸；而通过随后的氧功能团还原，可以转化为γ-羟基-α-氨基酸衍生物，这些转化反应均能获得较高的产率。由于γ-硝基-α-氨基酸衍生物是从N,O保护的脱氢丙氨酸制备而成，而后者又是通过特定途径从相应的丙氨酸、丝氨酸和半胱氨酸衍生物得到的，因此整体程序提供了一种选择性将这些简单的α-氨基酸转化为更复杂的氨基酸的方法。
• Spergualin-related compounds and process for the preparation thereof
  申请人：Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai

  公开号：US04529549A1

  公开（公告）日：1985-07-16

  This invention relates to a novel spergualin-related compound and a process for the production thereof. The novel compound, which has a high antitumor activity, is represented by the general formula ##STR1## wherein R.sub.1 represents a hydrogen atom, hydroxyl group, or an aliphatic acyloxy group having 1 to 10 carbon atoms, R.sub.2 represents an amino acid residue (except for the residue of .alpha.-hydroxyglycine) formed by removing one hydrogen atom and hydroxyl group from respectively the .alpha.- or .omega.-amino group and the .alpha.-carboxyl group of an .alpha.- or .omega.-amino acid, said amino acid residue forming acid amide linkages with the adjacent carbonyl group and amino group, and m is an integer of 4 to 6.

  本发明涉及一种新的与spergualin相关的化合物及其生产方法。这种具有高抗肿瘤活性的新化合物由一般公式##STR1##表示，其中R.sub.1代表氢原子、羟基或具有1至10个碳原子的脂肪酰氧基，R.sub.2代表氨基酸残基（除了α-羟基甘氨酸残基）由α-或ω-氨基和α-羧基中分别去除一个氢原子和羟基得到，该氨基酸残基与相邻的羰基和氨基形成酸酰胺键，m为4至6的整数。