(R)-tert-butyl 4-methylpent-1-yn-3-ylcarbamate | 213315-70-9

• 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: (R)-tert-butyl 4-methylpent-1-yn-3-ylcarbamate
• 英文别名: O-tert-butyl N-(R)-(4-methylpent-1-yn-3-yl)carbamate；tert-butyl [(1R)-1-isopropylprop-2-yn-1-yl]carbamate；Carbamic acid, [(1R)-1-(1-methylethyl)-2-propynyl]-, 1,1-dimethylethyl ester；tert-butyl N-[(3R)-4-methylpent-1-yn-3-yl]carbamate
• CAS: 213315-70-9
• 化学式: C₁₁H₁₉NO₂
• 分子量: 197.277
• InChiKey: XEDKAILLTLQJMB-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-tert-butyl 4-methylpent-1-yn-3-ylcarbamate 在 盐酸 、 N-羟基-7-氮杂苯并三氮唑 、 chloro(1,5-cyclooctadiene)(pentamethylcyclopentadiene)ruthenium(II) 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 2.17h， 生成 C₃₄H₄₄N₈O₅
  参考文献：
  名称：

  1,5-二取代的1,2,3-三唑-含肽三唑酰胺：一类多功能拟肽的设计原理

  摘要：

  肽三唑叠氮化合物是结合了肽和三唑叠氮化合物的特征的杂合折叠剂-重复的拟肽结构，三唑取代了肽键。我们报告了一种新的类肽模拟物的合成，该类肽模拟物以1,5-二取代的1,2,3-三唑与酰胺键交替出现，并对它们在固态和溶液中的构象进行了分析。钌催化的叠氮化物-炔烃环加成反应（RuAAC）是在微波条件下，以高收率从对映体纯的炔丙基胺（在炔丙基位置具有立体异构中心）和α-叠氮基酯获得对映体或手性肽三唑酰胺。具有这种结构单元的肽三唑并聚物可通过溶液相合成容易地获得。而同手性肽三唑唑Boc-Ala [5Tz]的构象PHE-VAL [5Tz]丙氨酸-亮氨酸[5Tz] VAL-OBzl计为类似于βVIa1转弯的是，所述异向peptidotriazolamer的Boc- d -Ala [5Tz] Phe- d -Val [5Tz] ALA- d -Leu [5Tz] Val‐OBzl采用类似脯氨酸的重复结构。

  DOI：

  10.1002/chem.201704583
• 作为产物：
  描述：

  在 盐酸 、 碳酸氢钠 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 1.0h， 生成 (R)-tert-butyl 4-methylpent-1-yn-3-ylcarbamate
  参考文献：
  名称：

  1,5-二取代的1,2,3-三唑-含肽三唑酰胺：一类多功能拟肽的设计原理

  摘要：

  肽三唑叠氮化合物是结合了肽和三唑叠氮化合物的特征的杂合折叠剂-重复的拟肽结构，三唑取代了肽键。我们报告了一种新的类肽模拟物的合成，该类肽模拟物以1,5-二取代的1,2,3-三唑与酰胺键交替出现，并对它们在固态和溶液中的构象进行了分析。钌催化的叠氮化物-炔烃环加成反应（RuAAC）是在微波条件下，以高收率从对映体纯的炔丙基胺（在炔丙基位置具有立体异构中心）和α-叠氮基酯获得对映体或手性肽三唑酰胺。具有这种结构单元的肽三唑并聚物可通过溶液相合成容易地获得。而同手性肽三唑唑Boc-Ala [5Tz]的构象PHE-VAL [5Tz]丙氨酸-亮氨酸[5Tz] VAL-OBzl计为类似于βVIa1转弯的是，所述异向peptidotriazolamer的Boc- d -Ala [5Tz] Phe- d -Val [5Tz] ALA- d -Leu [5Tz] Val‐OBzl采用类似脯氨酸的重复结构。

  DOI：

  10.1002/chem.201704583

文献信息

• Cu(I)-Catalyzed Synthesis of Dihydropyrimidin-4-ones toward the Preparation of β- and β³-Amino Acid Analogues
  作者：Basker Rajagopal、Ying-Yu Chen、Chun-Chi Chen、Xuan-Yu Liu、Huei-Ren Wang、Po-Chiao Lin

  DOI：10.1021/jo402670d

  日期：2014.2.7

  A copper(I)-catalyzed synthesis of substituted dihydropyrimidin-4-ones from propargyl amides via the formation of ketenimine intermediate has been successfully developed; the synthesis afforded good isolated yields (80–95%). The mild reaction conditions at room temperature allow the reaction to proceed to completion in a few hours without altering the stereochemistry. Further, by involving a variety

  已经成功地开发了铜（I）催化炔酮胺中间体从炔丙基酰胺合成取代的二氢嘧啶-4-酮。合成得到良好的分离产率（80-95％）。室温下温和的反应条件可使反应在数小时内完成，而无需改变立体化学。另外，通过涉及多种反应性亲核试剂，将得到的被取代的二氢嘧啶-4-酮被优雅转化成相应的β-和β 3 -氨基酸的类似物。
• Macrocyclic Ghrelin Receptor Antagonists and Inverse Agonists and Methods of Using the Same
  申请人：Hoveyda Hamid R.

  公开号：US20110105389A1

  公开（公告）日：2011-05-05

  The present invention provides novel conformationally-defined macrocyclic compounds that have been demonstrated to be selective modulators of the ghrelin receptor (GRLN, growth hormone secretagogue receptor, GHS-R1a and subtypes, isoforms and/or variants thereof). Methods of synthesizing the novel compounds are also described herein. These compounds are useful as antagonists or inverse agonists of the ghrelin receptor and as medicaments for treatment and prevention of a range of medical conditions including, but not limited to, metabolic and/or endocrine disorders, obesity and obesity-associated disorders, appetite or eating disorders, addictive disorders, cardiovascular disorders, gastrointestinal disorders, genetic disorders, hyperproliferative disorders, central nervous system disorders and inflammatory disorders.

  本发明提供了新型构象定义的大环化合物，已被证明是生长激素分泌素受体（GRLN，生长激素分泌素受体，GHS-R1a及其亚型、异构体和/或变种）的选择性调节剂。本文还描述了合成这些新型化合物的方法。这些化合物可用作生长激素分泌素受体的拮抗剂或逆向激动剂，以及用于治疗和预防一系列医学疾病，包括但不限于代谢和/或内分泌紊乱、肥胖和与肥胖相关的疾病、食欲或进食紊乱、成瘾紊乱、心血管疾病、胃肠道疾病、遗传疾病、过度增殖性疾病、中枢神经系统疾病和炎症性疾病。
• [EN] COMPOUNDS, COMPOSITIONS, AND METHODS<br/>[FR] COMPOSES, COMPOSITIONS ET PROCEDES
  申请人：CYTOKINETICS INC

  公开号：WO2003106426A1

  公开（公告）日：2003-12-24

  Compounds useful for treating cellular proliferative diseases and disorders by modulating the activity of KSP are disclosed.

  本发明揭示了通过调节KSP的活性来治疗细胞增殖性疾病和疾病的有用化合物。
• A reasonably stereospecific multistep conversion of Boc-protected α-amino acids to Phth-protected β3-amino acids
  作者：Andrea Temperini、Antonella Capperucci、Alessandro Degl’Innocenti、Raffaella Terlizzi、Marcello Tiecco

  DOI：10.1016/j.tetlet.2010.05.143

  日期：2010.8

  A method for the synthesis of beta(3)-amino acids starting from alpha-amino acids is described. This conversion can be effected by an eight-step procedure which involves the transformation of the carboxylic group into an alkyne followed by a selenium-mediated conversion of the carbon-carbon triple bond to a Se-phenyl selenocarboxylate intermediate. The reactive Se-phenyl selenocarboxylate intermediates can be trapped with water, alcohols or the amine of an amino acid derivative to give beta(3)-amino acids, beta(3)-amino esters or mixed peptides, respectively. The whole transformations of the carboxylic group into an alkyne and of the alkyne group into beta(3)-amino acids may not require purification of the intermediate products but a workup and isolation procedure of crude materials. (C) 2010 Elsevier Ltd. All rights reserved.
• [EN] MACROCYCLIC GHRELIN RECEPTOR ANTAGONISTS AND INVERSE AGONISTS AND METHODS OF USING THE SAME<br/>[FR] ANTAGONISTES ET AGONISTES INVERSES MACROCYCLIQUES DU RÉCEPTEUR DE LA GHRÉLINE ET LEURS MÉTHODES D'UTILISATION
  申请人：TRANZYME PHARMA INC

  公开号：WO2011053821A1

  公开（公告）日：2011-05-05

  The present invention provides novel conformationalIy- defined macrocyclic compounds of formula (I) that have been demonstrated to be selective modulators of the ghrelin receptor (GRLN, growth hormone secretagogue receptor, GHS-R1a and subtypes, isoforms and/or variants thereof). Methods of synthesizing the novel compounds are also described herein. These compounds are useful as antagonists or inverse agonists of the ghrelin receptor and as medicaments for treatment and prevention of a range of medical conditions including, but not limited to, metabolic and/or endocrine disorders, obesity and obesity- associated disorders, appetite or eating disorders, addictive disorders, cardiovascular disorders, gastrointestinal disorders, genetic disorders, hyperproliferative disorders, central nervous system disorders and inflammatory disorders.