(3-diazo-1-(R)-methyl-2-oxopropyl)carbamic acid benzyl ester | 68223-06-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3-diazo-1-(R)-methyl-2-oxopropyl)carbamic acid benzyl ester
• 英文别名: (3R)-1-diazo-3-(N-benzyloxycarbonylamino)-2-butanone；(R)-1-diazo-3-(benzyloxycarbonylamino)butan-2-one；benzyl [(2R)-4-diazo-3-oxobutan-2-yl]carbamate；N-benzyloxycarbonyl-D-alanylyl diazomethane；benzyl N-[(2R)-4-diazo-3-oxobutan-2-yl]carbamate
• CAS: 68223-06-3
• 化学式: C₁₂H₁₃N₃O₃
• 分子量: 247.254
• InChiKey: DOUDVLKNDXOMIW-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  57.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3-diazo-1-(R)-methyl-2-oxopropyl)carbamic acid benzyl ester 在 silver benzoate 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 methyl (2R,3R)-3-(((benzyloxy)carbonyl)amino)-2-methylbutanoate
  参考文献：
  名称：

  草pe内酯A的全合成及生物评价

  摘要：

  在本文中，我们全面描述了草皮肽A（1）分17线性步长，总收率为11.3％。特别是，这项工作的特点是后期引​​入了敏感的双（噻唑啉）杂环和在空间拥挤的仲酰胺位点进行了出色的转化（72％收率）的31元大环化。生物学评估表明，草肽内酯A以剂量依赖的方式显着抑制癌细胞的增殖。它诱导癌细胞凋亡，这与聚（ADP-核糖）聚合酶（PARP）的切割增加和bcl-2和bcl-xL的表达降低有关。此外，草肽A还通过增加G1期的细胞和减少S期和G2期的细胞而引起细胞周期的重新分布。另外，细胞周期停滞与细胞周期蛋白D的下调以及p27和p21的上调相关。

  DOI：

  10.1002/chem.201203667
• 作为产物：
  描述：

  N-benzyloxycarbonyl-D-alanine 在 三乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.5h， 生成 (3-diazo-1-(R)-methyl-2-oxopropyl)carbamic acid benzyl ester
  参考文献：
  名称：

  Synthesis and characterization of chiral di(N-protected-α-amino)diazo-β-diketones from α-diazoketones and imidazolides derived from amino acids

  摘要：

  Di(N-protected-alpha-amino)diazo-beta-diketones were prepared by the reaction of activated N-protected-alpha-amino acids (imidazolides) with alpha-diazoketones, derived from natural amino acids, in the presence of lithium diisopropylamide in tetrahydrofuran as the solvent at -78 degrees C. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.01.093

文献信息

• Synthesis and Evaluation of Ketophosph(on)ates as β-Lactamase Inhibitors
  作者：Senthil K. Perumal、R. F. Pratt

  DOI：10.1021/jo060364v

  日期：2006.6.1

  PhCH2OCONHCH(R)COCR‘N2. The electrophilicity of the carbonyl group in the resulting phosph(on)ates was assessed by the degree of hydration in aqueous solution, determined from NMR spectra. These compounds inhibited typical class C and class D β-lactamases, particularly the latter group, but showed no activity against class A enzymes. To enhance the carbonyl electrophilicity, an α-difluorinated analogue (R =

  一系列通式为PhCH 2 OCONHCH（R）COCHR'（CH 2）n（O）P（O 2 -）（O）R''（R = H，CH 3 ; R'= H，CH 3；n＝ 0，1； R′′＝ H，CH 3，Et，Ph）已经被制备作为β-内酰胺酶抑制剂的潜在来源。膦酸酯（n = 0）是通过Arbuzov反应获得的，而大多数磷酸盐则是通过磷酸（或/ on）酸与适当的重氮酮PhCH 2 OCONHCH（R）COCR'N 2的反应获得的。。通过由NMR光谱确定的水溶液中的水合度来评估所得的膦酸酯中羰基的亲电子性。这些化合物抑制典型的C类和D类β-内酰胺酶，特别是后者，但对A类酶没有活性。为了增强羰基亲电性，还制备了α-二氟类似物（R = H，CHR'= CF 2，n = 0，R''= Et），但是没有观察到增强的抑制活性。所有证据表明，这些化合物以羰基形式抑制，而不是通过在β-内酰胺酶活性位点形成四面体加合
• Total synthesis of polyoximic acid
  作者：Stephen Hanessian、Jian-min Fu

  DOI：10.1139/v01-171

  日期：2001.11.1

  structure and stereochemistry of polyoximic acid, a degradation product of polyoxins, was originally designated as trans-3-ethylidene-L-azetidine-2-carboxylic acid. However, total synthesis revealed that the correct structure was in fact cis-3-ethylidene-L-azetidine-2-carboxylic acid, which was confirmed by X-ray crystallography. The synthesis of the trans-isomer was also done and its identity was confirmed

  聚肟酸是一种多氧化合物的降解产物，其结构和立体化学最初被命名为反式-3-亚乙基-L-氮杂环丁烷-2-羧酸。然而，全合成表明正确的结构实际上是顺-3-亚乙基-L-氮杂环丁烷-2-羧酸，这通过X射线晶体学证实。反式异构体的合成也已完成，其身份也通过 X 射线分析得到证实。构建四元环的关键步骤是铑催化的类卡宾插入到β-氨基酸衍生物的N 2 H 键中。通过进行 Horner-Emmons-Wadsworth 或 Wittig 反应以分别产生反式和顺式异构体来控制外双键的立体选择性。温雷布' s 酰胺用作潜在的甲基，用于分离反式和顺式混合物。通过广泛的 2D NMR 研究也证实母体多肟中多肟酸的双键立体化学是顺式的。 关键词：重氮插入，...
• Complexation of Chiral Di (N-Protected a-Amino)-b-Diketones with Some Transition Metals
  作者：Ibrahim A.M. Saraireh

  DOI：10.14233/ajchem.2013.14080

  日期：——

  Chiral Di (N-protected a-amino)-b-diketones and its transition metal complexes have been synthesized. Di(N-protected a-amino)-b-diketones were prepared by reaction of activation of N-protected-a-amino acids (imidazolide) with a-diazoketones derived from natural amino acids in presence of lithium diisopropyl amid in tetrahydrofuran as a solvent at -78 ºC and treatment the product with rhodium acetate to remove diazo group. The synthesized compounds were characterized by analytical techniques viz: IR, NMR and elemental analysis. The thermal stability of the newly synthesized metal complexes have been studied.

  合成了手性二（N保护α-氨基）-β-二酮及其过渡金属复合物。二（N保护α-氨基）-β-二酮通过在-78 ºC的四氢呋喃溶剂中，利用锂二异丙基酰胺激活N保护的α-氨基酸（咪唑化物）与来自天然氨基酸的α-二氮基酮反应制备，并用醋酸铑处理产物以去除二氮基团。合成的化合物通过红外光谱（IR）、核磁共振（NMR）和元素分析等分析技术进行了表征。新合成的金属复合物的热稳定性也进行了研究。
• Chiral imidazole derivatives synthesis from enantiopure N-protected α-amino acids
  作者：Filip Bureš、Jiří Kulhánek

  DOI：10.1016/j.tetasy.2005.01.049

  日期：2005.4

  A route to the preparation of enantiopure ligands based on a 2-phenylimidazol ring is described. The stereogenic centre is placed into the chain bonded to the fourth carbon of the imidazole ring. The synthesis starts from inexpensive and readily available N-protected alpha-amino acids, as the source of chirality, which are converted into appropriate alpha-diazoketones and, consequently, into alpha-bromoketones. These alpha-bromoketones are good precursors for reactions with amidines to provide the imidazole ring. The deprotection into the final products was carried out using hydrogen. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis of N-Urethane Protected α-Aminoalkyl-α′-cyanomethyl Ketones; Application to the Synthesis of 3-Substituted 5-Amino-1H-pyrazole Tethered Peptidomimetics
  作者：Vommina Sureshbabu、M. Sharnabai、G. Nagendra

  DOI：10.1055/s-0032-1316586

  日期：2012.8

  The preparation of N-protected amino/peptide alpha-cyanomethyl ketones through cyanation of the corresponding alpha-bromomethyl ketones is described. The utility of the resulting acyanomethyl ketones in the synthesis of 3-substituted-5-amino-1H-pyrazoles has also been demonstrated. In both steps a wide range of N-protected amino/peptide acids has been employed and the products are obtained in good yield. The enantiomeric purity of both the alpha-cyanomethyl ketones and pyrazoles were confirmed by chiral HPLC analysis of the corresponding Z-protected D-and L-Ala-OH as model substrates. The synthesis of peptide pyrazolecarbox-amides is also delineated.