methyl (S)-3-methyl-2-(2-propynylamino)butanoate | 927384-16-5

• 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: methyl (S)-3-methyl-2-(2-propynylamino)butanoate
• 英文别名: methyl prop-2-yn-1-yl-L-valinate；N(α)-propargyl ValOMe；methyl (2S)-3-methyl-2-(prop-2-ynylamino)butanoate
• CAS: 927384-16-5
• 化学式: C₉H₁₅NO₂
• 分子量: 169.224
• InChiKey: UWGZMJFNGKEUNK-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (S)-3-methyl-2-(2-propynylamino)butanoate 在 sodium hydroxide 、 三乙基硼 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 (6S,6aR)-N-tert-butoxycarbonyl-6,6a-dihydro-6-isopropyl-2-oxo-2H-furo[3,2-c]-5-pyrrole
  参考文献：
  名称：

  Butenolide Synthesis by Molybdenum-Mediated Hetero-Pauson−Khand Reaction of Alkynyl Aldehydes

  摘要：

  The highly reactive complex Mo(CO)(3)(DMF)(3) promotes the CO gas-free cyclocarbonylation of 1,5- and 1,6-alkynyl aldehydes under very mild reaction conditions to provide fused butenolides in good yields. This novel Mo-mediated hetero-Pauson-Khand reaction is very general with regard to the substitution at the alkyne terminus and tether (18 tested cases). Using readily available chiral alkynyl aldehydes, this procedure has been applied to the enantio- and stereoselective synthesis of highly substituted bicyclic butenolides, including an intermediate in natural product synthesis.

  DOI：

  10.1021/ja0684186
• 作为产物：
  描述：

  L-缬氨酸甲酯 、 3-溴丙炔 在 lithium hydroxide 、 4 A molecular sieve 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.75h， 以61%的产率得到methyl (S)-3-methyl-2-(2-propynylamino)butanoate
  参考文献：
  名称：

  Butenolide Synthesis by Molybdenum-Mediated Hetero-Pauson−Khand Reaction of Alkynyl Aldehydes

  摘要：

  The highly reactive complex Mo(CO)(3)(DMF)(3) promotes the CO gas-free cyclocarbonylation of 1,5- and 1,6-alkynyl aldehydes under very mild reaction conditions to provide fused butenolides in good yields. This novel Mo-mediated hetero-Pauson-Khand reaction is very general with regard to the substitution at the alkyne terminus and tether (18 tested cases). Using readily available chiral alkynyl aldehydes, this procedure has been applied to the enantio- and stereoselective synthesis of highly substituted bicyclic butenolides, including an intermediate in natural product synthesis.

  DOI：

  10.1021/ja0684186

文献信息

• 3-Silaazetidine: An Unexplored yet Versatile Organosilane Species for Ring Expansion toward Silaazacycles
  作者：Wanshu Wang、Song Zhou、Linjie Li、Yuanhang He、Xue Dong、Lu Gao、Qiantao Wang、Zhenlei Song

  DOI：10.1021/jacs.1c04667

  日期：2021.7.28

  Small-ring silacycles are important organosilane species in main-group chemistry and have found numerous applications in organic synthesis. 3-Silaazetidine, a unique small silacycle bearing silicon and nitrogen atoms, has not been adequately explored due to the lack of a general synthetic scheme and its sensitivity to air. Here, we describe that 3-silaazetidine can be easily prepared in situ from diverse

  小环硅杂环化合物是主族化学中重要的有机硅烷物质，在有机合成中有着广泛的应用。3-硅氮杂环丁烷是一种独特的小硅环，含有硅和氮原子，由于缺乏通用合成方案及其对空气的敏感性，尚未得到充分探索。在这里，我们描述了 3-硅氮杂环丁烷可以很容易地从各种空气稳定的前体 (RSO 2 NHCH 2 SiR 1 2 CH 2CL）。3-硅氮杂环丁烷在钯催化的与末端炔烃的扩环反应中显示出优异的官能团耐受性，产生 3-硅杂四氢吡啶和多种硅氮杂环衍生物，它们是发现含硅功能分子的有前途的环骨架。
• Facile Entry to 4,5,6,7-Tetrahydro[1,2,3]triazolo[1,5-a]pyrazin-6-ones from Amines and Amino Acids
  作者：V. Sai Sudhir、R. B. Nasir Baig、Srinivasan Chandrasekaran

  DOI：10.1002/ejoc.200800036

  日期：2008.5

  A practical and high-yielding regioselective synthesis ofseveral enantiopure 4,5,6,7-tetrahydro[1,2,3]triazolo[1,5-a]pyrazin-6-ones is described starting from primary amines and α-amino acid derivatives in a three-step reaction sequence by employing a constrained intramolecular “click” reaction as the key step. The method obviates chromatographic purification of products.(© Wiley-VCH Verlag GmbH &

  从伯胺和α-氨基酸开始，描述了几种对映体纯的4,5,6,7-四氢[1,2,3]三唑并[1,5-a]吡嗪-6-酮的实用且高产的区域选择性合成通过采用受限的分子内“点击”反应作为关键步骤，在三步反应序列中生成衍生物。该方法避免了产品的色谱纯化。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008）
• Molecular Assembly of Multifunctional 99mTc Radiopharmaceuticals Using “Clickable” Amino Acid Derivatives
  作者：Thomas L. Mindt、Harriet Struthers、Bernhard Spingler、Luc Brans、Dirk Tourwé、Elisa García-Garayoa、Roger Schibli

  DOI：10.1002/cmdc.201000342

  日期：2010.12.3

  N(α)‐propargyl lysine derivatives, conjugates containing a 99mTc‐based imaging probe for SPECT and two different moieties (e.g., tumor‐targeting vectors, pharmacological modifiers, affinity tags, or second imaging probes) can be assembled using the CuI‐catalyzed alkyne–azide cycloaddition in efficient one‐pot protocols. This strategy was successfully applied to the preparation of a 99mTc‐labeled conjugate comprising

  能够有效和选择性地组合不同生物活性实体的合成策略，对于开发可用于生化和医学应用的多功能杂合缀合物具有广阔的前景。从侧链功能化的N（α）-炔丙基赖氨酸衍生物开始，结合物包含用于SPECT的99m Tc基成像探针和两个不同部分（例如，肿瘤靶向载体，药理修饰剂，亲和标签或第二个成像探针）可以使用Cu I催化的炔-叠氮化物环加成反应以高效的一锅法进行组装。该策略已成功应用于99m的准备Tc标记的偶联物包含靶向肿瘤的肽序列（bombesin（7-14））和低分子量白蛋白结合剂，这是一种可延长结合物血液循环时间的药理学修饰剂。在体外和体内对缀合物的评估为将其用作显像剂对胃泌素释放肽受体呈阳性的肿瘤的显像剂提供了有希望的结果。本文介绍的方法学为制备多功能的基于99m Tc的放射性药物提供了一种有吸引力的合成工具，具有广泛的应用潜力。