(S)-1-benzyl-N-(tert-butoxycarbonyl)-2-propynamine | 143327-79-1

• 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)-1-benzyl-N-(tert-butoxycarbonyl)-2-propynamine
• 英文别名: tert-butyl(1S)-1-benzylprop-2-ynylcarbamate；((S)-1-benzyl-2-propynyl)carbamic acid t-butyl ester；((S)-1-benzyl-2-prop-2-ynyl)carbamic acid t-butyl ester；Boc-(S)-dcPhe-CCH；tert-butyl [(1S)-1-benzylprop-2-yn-1-yl]carbamate；(S)-tert-butyl 1-phenylbut-3-yn-2-ylcarbamate；Boc-Phe-CCH；tert-butyl N-[(2S)-1-phenylbut-3-yn-2-yl]carbamate
• CAS: 143327-79-1
• 化学式: C₁₅H₁₉NO₂
• 分子量: 245.321
• InChiKey: NSTYAOIOBURIDL-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  (S)-1-benzyl-N-(tert-butoxycarbonyl)-2-propynamine 在 苯甲醚 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-1-phenylbut-3-yn-2-amine
  参考文献：
  名称：

  组蛋白去乙酰化酶抑制剂：环状四肽及其三唑类似物的合成

  摘要：

  描述了九个大环肽 HDAC 抑制剂和三个三唑衍生物的合成。评估了这些化合物对 HeLa 细胞裂解物的 HDAC 抑制活性。生物学数据表明，三唑单元的掺入提高了 HDAC 抑制活性。

  DOI：

  10.1016/j.tetlet.2010.06.050
• 作为产物：
  描述：

  N-Boc-L-苯丙氨醛 在 正丁基锂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 (S)-1-benzyl-N-(tert-butoxycarbonyl)-2-propynamine
  参考文献：
  名称：

  一种新的手性γ-官能化（E）-烯丙基胺的立体选择性合成

  摘要：

  从衍生自天然氨基酸的氨基醛开始获得手性t- Boc保护的炔丙基胺。这些底物的甲锡化提供了容易的区域控制和立体控制的途径，形成了相应的γ-甲氧基化（E）-烯丙胺，它们是合成相应的γ-官能化的烯丙基体系的有用中间体。

  DOI：

  10.1016/0040-4020(96)00617-5

文献信息

• Backbone-Fluorinated 1,2,3-Triazole-Containing Dipeptide Surrogates
  作者：Jens Engel-Andreasen、Isabelle Wellhöfer、Kathrine Wich、Christian A. Olsen

  DOI：10.1021/acs.joc.7b01744

  日期：2017.11.3

  incorporated as a peptide bond bioisostere to provide protease resistance in peptidomimetics. Herein, we report the synthesis of peptidomimetic building blocks containing backbone-fluorinated 1,4-disubstituted 1,2,3-triazole moieties. Synthetic protocols for the preparation of various Xaa-Gly dipeptide surrogates in the form of Xaa-ψ[triazole]-F2Gly building blocks were established, and selected examples were

  可以将1,2,3-三唑部分作为肽键生物等排体掺入以在拟肽中提供蛋白酶抗性。在这里，我们报道了含有骨架氟化的1，4-二取代的1,2,3-三唑部分的拟肽结构单元的合成。建立了用于制备Xaa-ψ[triazole] -F 2 Gly结构单元形式的各种Xaa-Gly二肽替代物的合成方案，并将选定的实例引入作为模型化合物的内源性阿片受体阿片受体配体亮脑啡肽。
• Triazolo-Peptidomimetics: Novel Radiolabeled Minigastrin Analogs for Improved Tumor Targeting
  作者：Nathalie M. Grob、Daniel Häussinger、Xavier Deupi、Roger Schibli、Martin Behe、Thomas L. Mindt

  DOI：10.1021/acs.jmedchem.9b01936

  日期：2020.5.14

  different tumors. Thus, radiolabeled MG11 derivatives have great potential for use in cancer diagnosis and therapy. A drawback of MG11 is its fast degradation by proteases, leading to moderate tumor uptake in vivo. We introduced 1,4-disubstituted 1,2,3-triazoles as metabolically stable bioisosteres to replace labile amide bonds of the peptide. The "triazole scan" yielded peptidomimetics with improved

  MG11是minigastrin的截短类似物，minigastrin是一种对胆囊收缩素2受体（CCK2R）具有高亲和力和特异性的肽，在不同的肿瘤中过表达。因此，放射性标记的MG11衍生物具有用于癌症诊断和治疗的巨大潜力。MG11的一个缺点是它可以被蛋白酶快速降解，从而导致体内中等程度的肿瘤吸收。我们引入了1,4-二取代的1,2,3-三唑作为代谢稳定的生物等排体，以取代该肽的不稳定酰胺键。“三唑扫描”产生的拟肽具有改善的对酶促降解的抗性和/或对CCK2R的亲和力。值得注意的是，我们的先导化合物的受体亲和力提高了10倍，导致体内肿瘤吸收提高了2.6倍。配体-CCK2R络合物的模型表明，芳香三唑部分与受体的Arg356残基的额外阳离子-π相互作用是造成这些现象的原因。我们首次展示了酰胺基至三唑的取代策略为药物开发提供了新的机遇，其超越了生物活性肽的代谢稳定性。
• Enantioselective Copper-Catalysed Propargylic Substitution: Synthetic Scope Study and Application in Formal Total Syntheses of (+)-Anisomycin and (−)-Cytoxazone
  作者：Remko J. Detz、Zohar Abiri、Remi le Griel、Henk Hiemstra、Jan H. van Maarseveen

  DOI：10.1002/chem.201003727

  日期：2011.5.16

  indoles excellent ee values were obtained (up to 98 % ee). The versatility of the propargylic amines obtained was demonstrated by their further elaboration to formal total syntheses of the antibiotic (+)‐anisomycin and the cytokine modulator (−)‐cytoxazone.

  使用具有手性吡啶-2-6-双恶唑啉（pybox）配体的铜催化剂将具有不同侧链（R = Ar，Bn，烷基）的各种炔丙基酯以很高的收率和良好的转化率转化为它们的胺对应物。对映选择性（最多90％对映体过量（ee））。反应中使用了不同的胺亲核试剂，苯胺及其类似物的对映选择性最高。有趣的是，也可以使用一些碳亲核试剂，并且吲哚具有优异的ee值（高达98％  ee）。进一步精制抗生素（+）-阿霉素和细胞因子调节剂（-）-cytoxazone的正式总合成证明了所获得的炔丙基胺的多功能性。
• INDOLE COMPOUND AS INHIBITOR OF NECROSIS
  申请人：LG LIFE SCIENCES LTD.

  公开号：US20160200709A1

  公开（公告）日：2016-07-14

  The present invention relates to an indole compound represented by formula (1), a pharmaceutically acceptable salt or isomer thereof, a composition for prevention or treatment of necrosis and necrosis-associated diseases, and a method for preparing the composition, the composition comprising the indole compound or the pharmaceutically acceptable salt or isomer thereof as an active ingredient.

  本发明涉及一种由式（1）表示的吲哚化合物，其药学上可接受的盐或异构体，用于预防或治疗坏死及与坏死相关疾病的组合物，以及制备该组合物的方法，该组合物包括所述吲哚化合物或其药学上可接受的盐或异构体作为活性成分。
• 알카인을 이용한 아마이드 화합물의 제조방법 및 이를 이용한 펩타이드 제조 방법
  申请人：Seoul National University R&DB Foundation 서울대학교산학협력단(120070509242) Corp. No ▼ 114371-0009224BRN ▼119-82-03684

  公开号：KR20170011773A

  公开（公告）日：2017-02-02

  본 발명은 전이금속촉매의 존재 하에 알카인 및 N-하이드록시 화합물을 유기용매 내에서 교반하여 아마이드 결합을 형성시키는 단계를 포함하는 아마이드 화합물의 제조방법 및 이를 이용한 펩타이드 제조방법에 관한 것으로, 본 발명에 의한 아마이드화 반응은 기존의 단순한 친핵성 및 친전자성과 같은 극성 반응성에 의존하지 않고 알카인과 전이금속의 배위결합 반응성에서 도출된 반응을 기반으로 하여 탁월한 화학선택성을 나타낸다. 또한, 펩타이드 합성시 소모적인 보호기 부착 및 탈착 반응 단계를 필요로 하지 않고 반응공정이 간단하여 폴리펩타이드 계열의 화합물을 합성하는데 매우 효과적일 뿐 아니라 반응 도중 출발물질이 소실되지 않기 때문에 100%의 원자경제성을 갖는다.

  This invention relates to a method for producing amide compounds, which includes a step of stirring alkaline and N-hydroxy compounds in an organic solvent under the presence of a transition metal catalyst to form amide bonds, and a peptide production method using the same. The amide reaction according to the present invention is based on the reactivity derived from the coordination reaction between alkaline and transition metals, rather than relying on conventional polar reactions such as simple nucleophilic and electrophilic reactions, demonstrating excellent chemical selectivity. Furthermore, the peptide synthesis process does not require consuming protective group attachment and detachment reactions, and the reaction process is simple, making it very effective for synthesizing compounds in the polyamide series, while also maintaining 100% atom efficiency as the starting materials are not lost during the reaction.