N-(tert-butoxycarbonyl)-(L)-alanine (S)-1-phenylethylamide | 166945-52-4

• 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: N-(tert-butoxycarbonyl)-(L)-alanine (S)-1-phenylethylamide
• 英文别名: tert-butyl N-[(2S)-1-oxo-1-[[(1S)-1-phenylethyl]amino]propan-2-yl]carbamate
• CAS: 166945-52-4
• 化学式: C₁₆H₂₄N₂O₃
• 分子量: 292.378
• InChiKey: MYPFBQNGZOYIBQ-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(tert-butoxycarbonyl)-(L)-alanine (S)-1-phenylethylamide 在 盐酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 (2S)-2-amino-N-[(1S)-1-phenylethyl]propanamide;hydrochloride
  参考文献：
  名称：

  Identification and SAR of Glycine Benzamides as Potent Agonists for the GPR139 Receptor

  摘要：

  A focused high throughput screening for GPR139 was completed for a select 100K compounds, and new agonist leads were identified. Subsequent analysis and structure-activity relationship studies identified (S)-3-chloro-N-(2-oxo-2-((1-phenylethyl)amino)ethyl)benzamide 7c as a potent and selective agonist of hGPR139 with an EC50 = 16 nM. The compound was found to cross the blood-brain barrier and have good drug-like properties amenable for oral dosing in rat.

  DOI：

  10.1021/acsmedchemlett.5b00247
• 作为产物：
  描述：

  N-叔丁氧羰基-L-丙氨酸 在 碘 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 N-(tert-butoxycarbonyl)-(L)-alanine (S)-1-phenylethylamide
  参考文献：
  名称：

  使用 I2/PPh3 从羧酸合成 N-羟基琥珀酰亚胺酯、N-酰基糖精和活化酯

  摘要：

  描述了一种合成可分离的活性酯的方法，其中用三苯基膦、碘和三乙胺处理羧酸。以此方式可获得的活性酯包括N-羟基琥珀酰亚胺酯、 N-羟基邻苯二甲酰亚胺酯( N- (酰氧基)邻苯二甲酰亚胺)、 N-酰基糖精、五氟苯酚酯、五氯苯酚酯、 N-羟基苯并三唑酯和六氟-2-丙醇酯。该方法可以类似地应用于N-酰基糖精和N-酰基咪唑的形成。该方法适用于芳香族和脂肪族活化酸以及α-氨基酸衍生物的可分离活性酯的形成。这些产品广泛应用于有机合成、肽合成、药物化学和化学生物学（例如，用于生物共轭）。该方法底物范围广泛，使用的试剂简单廉价，避免使用碳二亚胺或其他偶联剂，并且在室温下进行。此外，化合物 Boc-Ala–NHCHPh 的非对映异构体被证明可以通过1 H NMR（在 DMSO- d 6中）区分，从而可以使用简单的 NMR 方法来确定 Boc-Ala 或酰胺键的活化酯的外消旋程度使用 Boc-Ala 编队。

  DOI：

  10.1021/acs.joc.4c00272

文献信息

• Enantioswitchable Catalysts for the Asymmetric Transfer Hydrogenation of Aryl Alkyl Ketones
  作者：Alexey B. Zaitsev、Hans Adolfsson

  DOI：10.1021/ol062227q

  日期：2006.10.1

  ruthenium-catalyzed reduction of ketones under hydrogen transfer conditions. In addition, in most cases, a switch of the product's absolute configuration was observed on going from amides to the corresponding thioamides. Under optimized conditions, we obtained the secondary alcohol products in high yield and enantioselectivity (up to 97% ee) using only 0.25 mol % catalyst loading. [structure: see text]

  配体结构的细微变化，用简单的α-氨基酸酰胺中的硫取代了羰基氧，在氢转移条件下，铑或钌催化的酮还原反应具有显着的活性和选择性改善。另外，在大多数情况下，在从酰胺转变为相应的硫代酰胺时，观察到了产品绝对构型的转变。在优化的条件下，仅使用0.25 mol％的催化剂负载量，我们即可获得高收率和对映选择性（最高97％ee）的仲醇产品。[结构：见文字]
• Highly modular dipeptide-like organocatalysts for direct asymmetric aldol reactions in brine
  作者：Xiao-Mu Hu、Dong-Xu Zhang、Sheng-Yong Zhang、Ping-An Wang

  DOI：10.1039/c5ra07019h

  日期：——

  dipeptide-like organocatalysts derived from proline, amino acids and primary amines have been prepared for direct asymmetric aldol reactions between various aromatic aldehydes and acetone to afford aldol products in good yields (up to 82%) and moderate enantioselectivities (up to 67% ee) with only 1 mol% of catalyst-loading in brine. Under the same conditions, the direct asymmetric aldol reactions of aromatic

  已经制备了一系列新的衍生自脯氨酸，氨基酸和伯胺的二肽样有机催化剂，用于各种芳族醛和丙酮之间的直接不对称羟醛反应，从而以良好的收率（最高82％）和中等的对映选择性（最高可达90％）提供羟醛产物。 67％ee），只有1 mol％的催化剂负载在盐水中。在相同条件下，芳族醛与环己酮的直接不对称羟醛反应可得到高收率（高达91％）和中等至良好的对映选择性（高达88％ee）和优异的非对映选择性（高达99％dr）的羟醛产物。这些有机催化剂很容易从市售材料中以多克规模合成，并在其结构和立体感方面具有高度的模块化。
• A Fluorous Capping Strategy for Fmoc-Based Automated and Manual Solid-Phase Peptide Synthesis
  作者：Vittorio Montanari、Krishna Kumar

  DOI：10.1002/ejoc.200500958

  日期：2006.2

  Just add water: Peptides synthesized by the use of standardized Fmoc protocols with commercial automated synthesizers can be purified from deletion products by simple centrifugation of aqueous solutions. The deletion products are capped with fluorous trivalent iodonium salts. At the end of the synthesis, the crude peptide is dissolved in water and centrifuged, and the deletion products precipitate

  只需加水：通过使用标准 Fmoc 协议和商业自动化合成仪合成的肽可以通过水溶液的简单离心从缺失产物中纯化出来。缺失产物用氟三价碘鎓盐封端。在合成结束时，粗肽溶解在水中并离心，缺失产物沉淀，只留下全长肽在溶液中。报告了普遍使用该策略的协议。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Proline-based dipeptides with two amide units as organocatalyst for the asymmetric aldol reaction of cyclohexanone with aldehydes
  作者：Fubin Chen、Shi Huang、Hui Zhang、Fengying Liu、Yungui Peng

  DOI：10.1016/j.tet.2008.07.051

  日期：2008.9

  A series of proline-based dipeptide organocatalysts with two amide units (1-16) have been developed and evaluated in the direct catalytic asymmetric aldol reactions of aldehydes with cyclohexanone. These catalysts showed good solubility in organic solvents compared with their corresponding carboxyl terminal dipeptides. The robust amide bond formation allowed structural modifications and fine tuning of catalyst properties by varying the stereo and electronic effects of the terminal amide to affect the ability of hydrogen bonding formation between the catalysts and the substrates. The reactions proceeded smoothly in high yields (up to 99%), enantioselectivities (up to 98% ee) and anti-diastereoselectivities (up to 99:1) in the presence of bifunctional organocatalyst 4 under the optimal reaction conditions. (C) 2008 Elsevier Ltd, All rights reserved.
• Identification and SAR of Glycine Benzamides as Potent Agonists for the GPR139 Receptor
  作者：Curt A. Dvorak、Heather Coate、Diane Nepomuceno、Michelle Wennerholm、Chester Kuei、Brian Lord、David Woody、Pascal Bonaventure、Changlu Liu、Timothy Lovenberg、Nicholas I. Carruthers

  DOI：10.1021/acsmedchemlett.5b00247

  日期：2015.9.10

  A focused high throughput screening for GPR139 was completed for a select 100K compounds, and new agonist leads were identified. Subsequent analysis and structure-activity relationship studies identified (S)-3-chloro-N-(2-oxo-2-((1-phenylethyl)amino)ethyl)benzamide 7c as a potent and selective agonist of hGPR139 with an EC50 = 16 nM. The compound was found to cross the blood-brain barrier and have good drug-like properties amenable for oral dosing in rat.