2-甲基-2-丙基[(3S)-4-甲基-1-戊炔-3-基]氨基甲酸酯 | 143327-78-0

• 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
• 中文名称: 2-甲基-2-丙基[(3S)-4-甲基-1-戊炔-3-基]氨基甲酸酯
• 中文别名: 5-甲磺酰氨基-6-苯氧基-1-铟烷酮
• 英文名称: (S)-tert-butyl (4-methylpent-1-yn-3-yl)carbamate
• 英文别名: O-tert-butyl N-(S)-(4-methylpent-1-yn-3-yl)carbamate；Boc-(S)-dcVal-CCH；tert-butyl [(1S)-1-isopropylprop-2-yn-1-yl]carbamate；tert-butyl 4-methylpent-1-yn-3-ylcarbamate；Carbamic acid, [(1S)-1-(1-methylethyl)-2-propynyl]-, 1,1-dimethylethyl ester；tert-butyl N-[(3S)-4-methylpent-1-yn-3-yl]carbamate
• CAS: 143327-78-0
• 化学式: C₁₁H₁₉NO₂
• 分子量: 197.277
• InChiKey: XEDKAILLTLQJMB-SECBINFHSA-N

物化性质

• 沸点：
  267.0±23.0 °C(Predicted)
• 密度：
  0.953±0.06 g/cm3(Predicted)

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：

  2-甲基-2-丙基[(3S)-4-甲基-1-戊炔-3-基]氨基甲酸酯 在 盐酸 、 bis(acetylacetonate)nickel(II) 、 Schwartz's reagent 、 二异丁基氢化铝 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 生成 3-[(E,3S)-3-amino-4-methylpent-1-enyl]cyclopentan-1-one
  参考文献：
  名称：

  Design and synthesis of novel FKBP inhibitors

  摘要：

  Small molecule FKBP inhibitors were prepared with inhibitory activity ranging from micromolar to nanomolar. The design of these inhibitors derives from a structural analysis of the substrates for FKBP and cyclophilin. As a consequence of this analysis two key observations were made, namely: (1) amino ketone moieties are suitable as FKBP recognition elements at the P1-P1' site and (2) the P3'-P4' site will accept a trans-olefin as a suitable mimetic of a peptide moiety. The preparation of these non-peptide inhibitors is readily accomplished by a protocol which includes the synthesis of chiral propargylic amines and their subsequent conversion into vinyl zirconium reagents.

  DOI：

  10.1021/jm00101a005
• 作为产物：
  描述：

  (S)-2-methoxy-N-(4-methylpent-1-yn-3-yl)aniline 在 碘苯二乙酸 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 21.0h， 生成 2-甲基-2-丙基[(3S)-4-甲基-1-戊炔-3-基]氨基甲酸酯
  参考文献：
  名称：

  对映选择性铜催化的炔丙基取代：（+）-阿霉素和（-）-Cyxoxazone的形式总合成中的合成范围研究和应用

  摘要：

  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。

  DOI：

  10.1002/chem.201003727

文献信息

• ALPHA2B AND ALPHA2C AGONISTS
  申请人：Takeuchi Janet A.

  公开号：US20090275627A1

  公开（公告）日：2009-11-05

  Described herein are compounds that can be useful as bioactive agents. More specifically, the compounds described herein can be useful as both α 2B and α 2C adrenergic agonists. Methods of synthesis and administration of the compounds are also disclosed.

  本文描述了一些可以作为生物活性剂的化合物。更具体地说，本文描述的化合物可以作为α2B和α2C肾上腺素受体激动剂。同时还公开了这些化合物的合成和给药方法。
• 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.
• 1,2,3-Triazoles as Amide Bond Mimics: Triazole Scan Yields Protease-Resistant Peptidomimetics for Tumor Targeting
  作者：Ibai E. Valverde、Andreas Bauman、Christiane A. Kluba、Sandra Vomstein、Martin A. Walter、Thomas L. Mindt

  DOI：10.1002/anie.201303108

  日期：2013.8.19

  The triazole makes the difference: Replacement of amide bonds in the backbone of peptides by 1,4‐disubstituted 1,2,3‐triazole isosteres affords peptidomimetics with retained receptor affinity and cell‐internalization properties, enhanced proteolytic stability, and improved tumor‐targeting capabilities.

  三唑的作用与众不同：用1,4-二取代的1,2,3-三唑等位基因取代肽主链中的酰胺键可提供拟肽，具有保留的受体亲和力和细胞内在化特性，增强了蛋白水解的稳定性，并改善了肿瘤靶向性能力。
• A new stereoselective synthesis of chiral γ-functionalized (E)-allylic amines
  作者：Gianna Reginato、Alessandro Mordini、Flavia Messina、Alessandro Degl'Innocenti、Giovanni Poli

  DOI：10.1016/0040-4020(96)00617-5

  日期：1996.8

  Chiral t-Boc protected propargylic amines have been obtained starting from aminoaldehydes derived from natural aminoacids. Stannylcupration of these substrates affords an easy regio- and stereocontrolled route to the corresponding γ-stannylated (E)-allylamines which are useful intermediates for the synthesis of the corresponding γ-funtionalized allylic systems.

  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。
• 1,5-Disubstituted 1,2,3-Triazole-Containing Peptidotriazolamers: Design Principles for a Class of Versatile Peptidomimetics
  作者：Oliver Kracker、Jerzy Góra、Joanna Krzciuk-Gula、Antoine Marion、Beate Neumann、Hans-Georg Stammler、Anke Nieß、Iris Antes、Rafał Latajka、Norbert Sewald

  DOI：10.1002/chem.201704583

  日期：2018.1.19

  With such building blocks the peptidotriazolamers are readily available by solution phase synthesis. While the conformation of the homochiral peptidotriazolamer Boc‐Ala[5Tz]Phe‐Val[5Tz]Ala‐Leu[5Tz]Val‐OBzl resembles that of a β VIa1 turn, the heterochiral peptidotriazolamer Boc‐d‐Ala[5Tz]Phe‐d‐Val[5Tz]Ala‐d‐Leu[5Tz]Val‐OBzl adopts a polyproline‐like repetitive structure.

  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。