((S)-2-Imidazol-1-yl-1-methyl-2-oxo-ethyl)-carbamic acid benzyl ester | 99790-15-5

• 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: ((S)-2-Imidazol-1-yl-1-methyl-2-oxo-ethyl)-carbamic acid benzyl ester
• 英文别名: benzyl N-[(2S)-1-imidazol-1-yl-1-oxopropan-2-yl]carbamate
• CAS: 99790-15-5
• 化学式: C₁₄H₁₅N₃O₃
• 分子量: 273.291
• InChiKey: NZDKFNATCWSVHE-NSHDSACASA-N

物化性质

• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.84
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  73.22
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ((S)-2-Imidazol-1-yl-1-methyl-2-oxo-ethyl)-carbamic acid benzyl ester 在 sodium tetrahydroborate 、 二异丁基氢化铝 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.08h， 生成 N-苄氧基羰基-L-丙氨醇
  参考文献：
  名称：

  A rapid and efficient one-pot method for the reduction of N-protected α-amino acids to chiral α-amino aldehydes using CDI/DIBAL-H

  摘要：

  N-保护的α-氨基酸可以通过使用CDI激活后再用DIBAL-H还原，在一个步骤中轻松直接转化为手性α-氨基醛。

  DOI：

  10.1039/c5ob01838b
• 作为产物：
  描述：

  苄氧羰基-L-丙氨酸 、 N,N'-羰基二咪唑 以 四氢呋喃 为溶剂， 反应 5.5h， 生成 ((S)-2-Imidazol-1-yl-1-methyl-2-oxo-ethyl)-carbamic acid benzyl ester
  参考文献：
  名称：

  新型dolastatin 10类似物的合成和抗肿瘤活性。

  摘要：

  Dolastatin 10（1）是有效的抗肿瘤五肽。合成了各自在组成氨基酸衍生物之一上修饰的新型dolastatin 10类似物，并评估了其对小鼠中P388白血病的抗肿瘤活性。讨论了抗肿瘤活性的结构要求。一些类似物31c，35c，38b和50c在体内显示出出色的活性。选择没有噻唑基团1的高活性50c作为抗肿瘤剂进行进一步开发。

  DOI：

  10.1248/cpb.43.1706

文献信息

• Synthesis and preliminary biological evaluations of (+)-isocampholenic acid-derived amides
  作者：Uroš Grošelj、Amalija Golobič、Damijan Knez、Martina Hrast、Stanislav Gobec、Sebastijan Ričko、Jurij Svete

  DOI：10.1007/s11030-016-9668-9

  日期：2016.8

  The synthesis of two novel (+)-isocampholenic acid-derived amines has been realized starting from commercially available (1S)-(+)-10-camphorsulfonic acid. The novel amines as well as (+)-isocampholenic acid have been used as building blocks in the construction of a library of amides using various aliphatic, aromatic, and amino acid-derived coupling partners using BPC and CDI as activating agents. Amide

  从市售的（1 S）-（+）-10-樟脑磺酸开始，已经实现了两种新颖的（+）-异马来酸衍生的胺的合成。在使用各种脂肪族，芳香族和氨基酸衍生的偶联伙伴（使用BPC和CDI作为活化剂）构建酰胺库的过程中，已将新型胺以及（+）-异马来酸用作结构单元。已对酰胺衍生物进行了针对几种酶的分析，这些酶具有开发新药来对抗细菌感染和阿尔茨海默氏病的潜力。化合物20c和20e显示出对人类丁酰胆碱酯酶\（（h \ hbox BChE}）\）  （\（\ hbox IC} _ 50} \）的选择性亚微摩尔抑制作用值分别为\（0.80 \，\ pm 0.05 \）和\（0.25 \，\ pm 0.02 \，\ upmu} \ hbox M} \）。
• N-carbamate protected amino acid derived guanidine organocatalysts
  作者：Zahraa S. Al-Taie、Joseph M. Anderson、Laura Bischoff、Jeppe Christensen、Simon J. Coles、Richard Froom、Mari E. Gibbard、Leigh F. Jones、Frank F.J. de Kleijne、Patrick J. Murphy、Emma C. Thompson

  DOI：10.1016/j.tet.2021.132093

  日期：2021.6

  We report the preparation of a range of N-protected amino acid derived guanidine organocatalysts and their application to the Michael addition of 2-hydroxy-1,4-napthoquinone to β-nitrostyrene, achieving a maximum ee of 26%. Whilst these catalysts gave poor ees, the structural variation together with the X-ray crystallographic study of the intra- and intermolecular hydrogen bonding reported suggest

  我们报告了一系列N-保护氨基酸衍生的胍有机催化剂的制备及其在 2-羟基-1,4-萘醌与 β-硝基苯乙烯的迈克尔加成中的应用，实现了 26% 的最大 ee。虽然这些催化剂的 ees 较差，但结构变化以及分子内和分子间氢键的 X 射线晶体学研究表明，C 2对称催化剂是该方法进一步发展的先导化合物。
• INTERMEDIATES AND METHODS FOR SEROTONERGIC AGONIST SYNTHESIS
  申请人：Delgado Pete

  公开号：US20080033184A1

  公开（公告）日：2008-02-07

  Disclosed is a method of making a 1-alkylindazole comprising reacting a 1-acylindazole with a first reducing agent, and contacting the resulting mixture with an acid anhydride or acyl halide, and with pyridine or a 4-dialkylaminopyridine or a combination of pyridine and a 4-dialkylaminopyridine, to form a hemiaminal ester and reacting the hemiaminal ester with a second reducing agent to form a 1-alkylindazole. Also disclosed are intermediates for the synthesis of 1-alkylindazoles.

  揭示了一种制备1-烷基吲唑的方法，包括将1-酰基吲唑与第一还原剂反应，然后将得到的混合物与酸酐或酰卤反应，以及与吡啶或4-二烷基氨基吡啶或吡啶和4-二烷基氨基吡啶的组合反应，形成半胺酯，然后将半胺酯与第二还原剂反应形成1-烷基吲唑。还揭示了合成1-烷基吲唑的中间体。
• Total Synthesis of Halipeptins A and D and Analogues
  作者：K. C. Nicolaou、David W. Kim、Daniel Schlawe、Dimitrios E. Lizos、Rita G. de Noronha、Deborah A. Longbottom

  DOI：10.1002/anie.200500702

  日期：2005.8.5
• Peptidomimetic Inhibitors of the Human Cytomegalovirus Protease
  作者：William Ogilvie、Murray Bailey、Marc-André Poupart、Abraham、Amit Bhavsar、Pierre Bonneau、Josée Bordeleau、Yves Bousquet、Catherine Chabot、Jean-Simon Duceppe、Gulrez Fazal、Sylvie Goulet、Chantal Grand-Maître、Ingrid Guse、Ted Halmos、Pierre Lavallée、Michael Leach、Eric Malenfant、Jeff O'Meara、Raymond Plante、Céline Plouffe、Martin Poirier、François Soucy、Christiane Yoakim、Robert Déziel

  DOI：10.1021/jm970104t

  日期：1997.12.1

  The development of peptidomimetic inhibitors of the human cytomegalovirus (HCMV) :protease showing sub-micromolar potency in an enzymatic assay is described. Selective substitution of the amino acid residues of these inhibitors led to the identification of tripeptide inhibitors showing improvements in inhibitor potency cf 27-fold relative to inhibitor 39 based upon the natural tetrapeptide sequence. Small side chains at P-1 were well tolerated by this enzyme, a fact consistent with previous observations. The S-2 binding pocket of HCMV protease was very permissive, tolerating lipophilic and basic residues. The substitutions tried at P-3 indicated that a small increase in inhibitor potency could be realized by the substitution of a tert-leucine residue for valine. Substitutions of the N-terminal capping group did not significantly affect inhibitor potency. Pentafluoroethyl ketones, alpha,alpha-difluoro-beta-keto amides, phosphonates and a-keto amides were all effective substitutions for the activated carbonyl component and gave inhibitors which were selective for HCMV protease. A slight increase in potency was observed by lengthening the P-1' residue of the alpha-keto amide series of inhibitors. This position also tolerated a variety of groups making this a potential site for future modifications which could modulate the physicochemical properties of these molecules.