Boc-L-Phe-N-pyrrolidinyl | 125139-05-1

• 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: Boc-L-Phe-N-pyrrolidinyl
• 英文别名: N^α-(tert-butoxycarbonyl)-L-phenylalanine-N-pyrrolidinamide；tert-butyl (S)-(1-oxo-3-phenyl-1-(pyrrolidin-1-yl)propan-2-yl)carbamate；Boc-L-phenyl-alaninepyrrolidine amide；Boc-Phe；tert-butyl (S)-1-oxo-3-phenyl-1-(pyrrolinin-1-yl)propan-2-carbamate；(S)-[2-Oxo-1-(phenylmethyl)-2-(1-pyrrolidinyl)ethyl]-carbamic acid 1,1-dimethylethyl ester；tert-butyl N-[(2S)-1-oxo-3-phenyl-1-pyrrolidin-1-ylpropan-2-yl]carbamate
• CAS: 125139-05-1
• 化学式: C₁₈H₂₆N₂O₃
• 分子量: 318.416
• InChiKey: HFLJUSDUGUQELQ-HNNXBMFYSA-N

物化性质

• 熔点：
  56 °C
• 沸点：
  502.0±50.0 °C(Predicted)
• 密度：
  1.123±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Boc-L-Phe-N-pyrrolidinyl 在 乙酰氯 作用下， 以 甲醇 为溶剂， 以3.71 g的产率得到1-(N-苯丙氨酰)吡咯烷
  参考文献：
  名称：

  天然氨基酸衍生的手性伯叔叔二胺催化剂用于羟基酮的顺式-羟醛反应

  摘要：

  从伯天然氨基酸设计合成了一系列伯叔二胺催化剂。这些新的手性催化剂在α-羟基酮的直接醛醇缩合反应中的应用显示出非常好的催化活性（高达97％的收率）和高的合成选择性（高达syn / anti = 30：1，99％ee）。

  DOI：

  10.1021/jo802557p
• 作为产物：
  描述：

  (S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropionamide 在 5A molecular sieve 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 Boc-L-Phe-N-pyrrolidinyl
  参考文献：
  名称：

  Efficient Transamidation of Primary Carboxamides by in Situ Activation with N,N-Dialkylformamide Dimethyl Acetals

  摘要：

  Two protocols for the transamidation of primary amides with primary and secondary amines, forming secondary and tertiary amides, respectively, are described. Both processes employ N,N-dialkylformamide dimethyl acetals for primary amide activation, producing N'-acyl-N,N-dialkylformamidines as intermediates, as widely documented in the literature. Although the latter intermediates react irreversibly with amines by amidinyl transfer, we show that in the presence of certain Lewis acid additives efficient acyl transfer occurs, providing new and useful methods for amide exchange. In one protocol for transamidation, the N'-acyl- N,N-dialkylformamidine intermediates are purified by flash-column chromatography and the purified intermediates are then treated with an amine (typically, 2.5 equiv) in the presence of scandium triflate (10 mol %) in ether to form in high yields the products of transamidation. In a second procedure, N'-acyl-N,N-dialkylformamidines are generated in situ and, without isolation, are subjected to transamidation in the presence of zirconium chloride (0.5 equiv) and an amine (typically 2 equiv). A variety of different primary amides and amines are found to undergo efficient transamidation using the methods described.

  DOI：

  10.1021/ja066728i

文献信息

• Dual‐protected amino acid derivatives as new antitubercular agents
  作者：Pedro P. Castro、Débora L. Campos、Fernando R. Pavan、Giovanni W. Amarante

  DOI：10.1111/cbdd.13315

  日期：2018.8

  drug-resistant rates. In an attempt to develop new antitubercular agents, 35 compounds were synthesized, most of them bearing a carbamate and enantiopure amino acid moiety. These compounds had their activity evaluated toward a Mycobacterium tuberculosis strain (ATCC 27294) and cytotoxicity against fibroblast MRC-5 cells (ATCC CCL-171). Three of the prepared derivatives presented a good antimicrobial inhibition

  结核病是一种传染病，发病率高，耐药率不断上升。为了开发新的抗结核药，合成了35种化合物，其中大多数带有氨基甲酸酯和对映体纯氨基酸部分。评估了这些化合物对结核分枝杆菌菌株的活性（ATCC 27294）和对成纤维细胞MRC-5细胞的细胞毒性（ATCC CCL-171）。所制备的三种衍生物具有良好的抗菌抑制作用，其中两种具有中等的细胞毒性。亲脂性似乎在细胞生长活性中起着至关重要的作用，对于具有较高logP的衍生物而言，其效果最佳。
• Chiral Primary Amine Catalyzed Asymmetric Direct Cross-Aldol Reaction of Acetaldehyde
  作者：Shenshen Hu、Long Zhang、Jiuyuan Li、Sanzhong Luo、Jin-Pei Cheng

  DOI：10.1002/ejoc.201100267

  日期：2011.6

  The first primary aminocatalytic direct cross-aldol reaction of acetaldehyde is presented. Among the various vicinal diamines screened, the L-tert-leucine derivative 1c in conjunction with (H4SiW12O40)0.25 was identified as the optimal catalyst; good catalytic activity (up to 99 % yield in 4 h), and high enantioselectivities (up to 92 % ee) were achieved for a range of donors, including aromatic aldehydes

  介绍了乙醛的第一个伯氨基催化直接交叉羟醛反应。在筛选的各种邻二胺中，L-叔亮氨酸衍生物1c与(H4SiW12O40)0.25结合被确定为最佳催化剂；对一系列供体（包括芳香醛和靛红衍生物）实现了良好的催化活性（4 小时内高达 99% 的产率）和高对映选择性（高达 92% ee）。乙醛水溶液和三聚乙醛可以方便地应用于该系统。
• Design of an Organocatalyst for the Enantioselective Diels−Alder Reaction with α-Acyloxyacroleins
  作者：Kazuaki Ishihara、Kazuhiko Nakano

  DOI：10.1021/ja053368a

  日期：2005.8.1

  derived from H-l-Phe-l-Leu-N(CH2CH2)2. The enantioselective Diels-Alder reaction of 5-(benzyloxymethyl)cyclopentadiene, cyclopentadiene, cyclohexadiene, 2,3-dimethylbutadiene, and isoprene with alpha-(p-methoxybenzoyloxy)acrolein catalyzed by the above chiral ammonium salt (2.5-20 mol %) at -20-22 degrees C gave the corresponding adducts with 83, 83, 91, 92, and 88% ee, respectively.

  我们已经实现了第一个对映选择性有机催化 Diels-Alder 反应，α 取代的丙烯醛，例如 α-酰氧基丙烯醛，不仅是环状二烯，还包括无环二烯。α-酰氧基丙烯醛可用作α-卤代丙烯醛的合成等价物。本催化剂可由五氟苯磺酸(2.5-3.0当量)和衍生自Hl-Phe-1-Leu-N(CH2CH2)2的手性三胺(1当量)原位制备。5-(苄氧基甲基)环戊二烯、环戊二烯、环己二烯、2,3-二甲基丁二烯和异戊二烯与α-(对甲氧基苯甲酰氧基)丙烯醛在上述手性铵盐(2.5-20 mol %)催化下的对映选择性Diels-Alder反应-20-22 摄氏度产生相应的加合物，分别为 83、83、91、92 和 88% ee。
• Cytotoxic Activity of Synthetic Chiral Amino Acid Derivatives
  作者：Pedro de Castro、Raoni Siqueira、Luiza Conforte、Chris Franco、Gustavo Bressan、Giovanni Amarante

  DOI：10.21577/0103-5053.20190157

  日期：——

  series of dual-protected amino acid derivatives was synthesized and evaluated as potential novel anticancer agents. The 40 derivatives were prepared in up to three reaction steps. The cytotoxic activities were screened in vitro against a panel of tumor and nontumor cells using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Among the synthesized derivatives, three of them showed

  癌症是一种慢性退行性疾病，被认为是全球范围内最重要的死亡原因之一。在这种情况下，合成了一系列双重保护的氨基酸衍生物，并将其评估为潜在的新型抗癌药。在多达三个反应步骤中制备了40种衍生物。使用3-（4,5-二甲基噻唑-2-基）-2,5-二苯基四唑溴化物（MTT）测定体外针对一组肿瘤和非肿瘤细胞的细胞毒性活性。在合成的衍生物中，其中三个显示出对癌细胞有希望的活性，其半数抑制浓度（IC50）在1.7-6.1μM之间。具有脂质亲和性N-烷基二胺部分和受保护的氨基酸支架的最有希望的衍生物显示出对肿瘤细胞的选择性指数为3.4。N-烷基二胺部分似乎在增强抗癌活性中起关键作用。另一方面，氨基酸支架的掺入导致对癌细胞系的选择性增加。
• Direct Synthesis of Amides from Carboxylic Acids and Amines Using B(OCH₂CF₃)₃
  作者：Rachel M. Lanigan、Pavel Starkov、Tom D. Sheppard

  DOI：10.1021/jo400509n

  日期：2013.5.3

  range of amines. In most cases, the amide products can be purified by a simple filtration procedure using commercially available resins, with no need for aqueous workup or chromatography. The amidation of N-protected amino acids with both primary and secondary amines proceeds effectively, with very low levels of racemization. B(OCH2CF3)3 can also be used for the formylation of a range of amines in good

  B(OCH 2 CF 3 ) 3由易得的B 2 O 3和2,2,2-三氟乙醇制备，是一种有效的试剂，可用于多种羧酸与多种胺的直接酰胺化。在大多数情况下，可以使用市售树脂通过简单的过滤程序纯化酰胺产物，无需进行水处理或色谱法。N-保护的氨基酸与伯胺和仲胺的酰胺化有效进行，外消旋化水平非常低。B(OCH 2 CF 3 ) 3 通过二甲基甲酰胺的转酰胺基作用，也可用于一系列胺的甲酰化反应，收率良好至极好。