(3R)-1-diazo-3-(N-benzyloxycarbonylamino)-4-phenyl-2-butanone | 114645-17-9

• 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: (3R)-1-diazo-3-(N-benzyloxycarbonylamino)-4-phenyl-2-butanone
• 英文别名: benzyl [(2R)-4-diazo-3-oxo-1-phenylbutan-2-yl]-carbamate；benzyl (R)-(4-diazo-3-oxo-1-phenylbutan-2-yl)carbamate；N-benzyloxycarbonyl-D-phenylalanylyl diazomethane；benzyl N-[(2R)-4-diazo-3-oxo-1-phenylbutan-2-yl]carbamate
• CAS: 114645-17-9
• 化学式: C₁₈H₁₇N₃O₃
• 分子量: 323.351
• InChiKey: WLGLEWHRLFWXLX-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  (3R)-1-diazo-3-(N-benzyloxycarbonylamino)-4-phenyl-2-butanone 在 sodium hydroxide 、 silver(l) oxide 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Peptidyl β-homo-aspartals: Specific inhibitors of interleukin-1β converting enzyme and its homologues (caspases)

  摘要：

  Inhibition of interleukin-1 beta converting enzyme (ICE), apopain, papain, thrombin and trypsin with substrate like peptidyl L- and D-alpha-aldehydes and their L-beta-homo-aldehyde analogues was investigated. The L-beta-homo-aspartals appear to be specific inhibitors for ICE and its homologues; the other enzymes were not inhibited with such L-beta-homo aldehydes. Papain shows tolerance for D-residues at P-1 depending on their chiral stability. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00244-3
• 作为产物：
  描述：

  重氮甲烷 、 (S)-(S)-2-(((benzyloxy)carbonyl)amino)-3-phenylpropanoic (isobutyl carbonic) anhydride 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.5h， 以6.4 g的产率得到(3R)-1-diazo-3-(N-benzyloxycarbonylamino)-4-phenyl-2-butanone
  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 of diazoketones derived from α-amino acids; problem of side reactions
  作者：Krystyna Plucińska、Bogdan Liberek

  DOI：10.1016/s0040-4020(01)81643-4

  日期：1987.1

  Optimum conditions of synthesis of eight diazoketones derived from optically active N-(t-butyloxycarbonyl)- and N-benzyloxycarbonylamino acids have been described. The problem of formation of by-products during Arndt-Eistert synthesis of β-homoamino acids at the stage of reaction of mixed anhydride with a weak nucleophile-diazomethane - has been discussed.

  已经描述了合成八种衍生自光学活性的N-（叔丁氧羰基）-和N-苄氧羰基氨基酸的重氮酮的最佳条件。讨论了在混合酸酐与弱亲核试剂-重氮甲烷反应的阶段，在Arndt-Eistert合成β-均氨基酸过程中形成副产物的问题。
• Metal-Free Insertion Reactions of Diazo Carbonyls to Azlactones
  作者：Amanda C. de Mello、Patrícia B. Momo、Antonio C. B. Burtoloso、Giovanni W. Amarante

  DOI：10.1021/acs.joc.8b01683

  日期：2018.9.21

  Insertion reactions of diazo carbonyls to azlactones in basic conditions have been performed. The developed method allows the preparation of a wide range of oxazole derivatives in yields ranging from 74 to 98%. Different substituents on both azlactone rings and diazo carbonyls do not compromise the methodology, even those containing stereogenic centers. Isotopic labeling experiments revealed the mechanism

  在碱性条件下已经进行了重氮羰基与氮杂内酯的插入反应。所开发的方法可以制备范围为74％至98％的各种恶唑衍生物。氮杂内酯环和重氮羰基上的不同取代基不会损害方法学，即使是那些含有立体异构中心的取代基。同位素标记实验表明，该机理可能是通过铵盐衍生物罕见的重氮羰基活化而进行的。
• 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。
• Vasanthakumar; Babu, V. V. Suresh, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 7, p. 1691 - 1695
  作者：Vasanthakumar、Babu, V. V. Suresh

  DOI：——

  日期：——