(S)-2-叔丁氧基羰基氨基-3-萘-2-基-丙酸甲酯 | 176896-73-4

• 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
• 中文名称: (S)-2-叔丁氧基羰基氨基-3-萘-2-基-丙酸甲酯
• 中文别名: 甲基N-{[(2-甲基-2-丙基)氧基]羰基}-3-(2-萘基)-L-丙氨酸酯
• 英文名称: methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(naphthalen-2-yl)propanoate
• 英文别名: methyl (S)-2-[(tert-butoxycarbonyl)amino]-3-(naphthalen-2-yl)propanoate；methyl (2S)-2-[N-(tert-butoxycarbonyl)amino]-3-(2-naphthyl)propionate；methyl 2-(S)-((tert-butoxycarbonyl)amino)-3-(2-naphthyl)propanoate；methyl (S)-2-tert-butoxycarbonylamino-3-(naphth-2-yl)propanoate；N-tert-butyloxycarbonyl 2-naphthylalanine methyl ester；Boc-2-Nal-OMe；Methyl N-Boc-3-(naphthalen-2-yl)-L-alaninate；methyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-naphthalen-2-ylpropanoate
• CAS: 176896-73-4
• 化学式: C₁₉H₂₃NO₄
• 分子量: 329.396
• InChiKey: GUZJZIQXCBCAGJ-INIZCTEOSA-N

物化性质

• 熔点：
  85-86 °C(Solv: hexane (110-54-3); ethyl ether (60-29-7))
• 沸点：
  487.6±38.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  (S)-2-叔丁氧基羰基氨基-3-萘-2-基-丙酸甲酯 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 2.5h， 以93%的产率得到L-naphthylalanine methyl ester hydrochloride
  参考文献：
  名称：

  Compounds and compositions for treating obesity

  摘要：

  本文描述了一种新颖且有用的化合物，其一般公式为。本发明的化合物可以有利地表现为黑色素皮质素受体激动剂活性。还描述了包含这种化学结构的新型和有用的化合物，以及通过给予这种化合物或组合物来调节受体在受试者中的活性（并促进、诱导和/或增强相关疾病的治疗或预防）的方法。

  公开号：

  US20070185128A1
• 作为产物：
  描述：

  (Z)-methyl 2-((tert-butoxycarbonyl)amino)-3-(naphthalen-2-yl)acrylate 在 bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate (R)-N-diphenylphosphino-N-methyl-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethylamine 、 氢气 作用下， 以 四氢呋喃 为溶剂， 25.0 ℃ 、68.95 kPa 条件下， 反应 6.0h， 生成 (S)-2-叔丁氧基羰基氨基-3-萘-2-基-丙酸甲酯
  参考文献：
  名称：

  Synthesis and Application of Phosphinoferrocenylaminophosphine Ligands for Asymmetric Catalysis

  摘要：

  [GRAPHICS]A new class of bidentate ligands utilizing a phosphine-aminophosphine structure has been prepared on a ferrocenylethyl backbone in a straightforward and scalable fashion from acetylferrocene. The unique property of the alpha-ferrocenyl carbonium ion that allows the replacement of a variety of "leaving groups" with retention of configuration greatly facilitates the synthesis, and a number of ligands have been prepared by varying the nitrogen and phosphorus substituents on the aminophosphine. These readily prepared phosphinoferrocenylaminophosphines, known as BoPhoz ligands, show surprising hydrolytic and air stability, with no degradation after 3 years open to the air. The rhodium complexes of these ligands show exceedingly high enantioselectivities (generally >95% ee) and activities often in excess of 50 000 catalyst turnovers per hour for the asymmetric hydrogenation of a wide variety of dehydro-alpha-amino acid and itaconic acid derivatives. They also show high activity and good to excellent enantioselectivity for the hydrogenation of a number of alpha-ketoesters.

  DOI：

  10.1021/jo048312y

文献信息

• Synthesis of Enantiopure Unnatural Amino Acids by Metallaphotoredox Catalysis
  作者：Tomer M. Faraggi、Caroline Rouget-Virbel、Juan A. Rincón、Mario Barberis、Carlos Mateos、Susana García-Cerrada、Javier Agejas、Oscar de Frutos、David W. C. MacMillan

  DOI：10.1021/acs.oprd.1c00208

  日期：2021.8.20

  wide array of optically pure unnatural amino acids. This method utilizes a photocatalytic cross-electrophile coupling between a bromoalkyl intermediate and a diverse set of aryl halides to produce artificial analogues of phenylalanine, tryptophan, and histidine. The reaction is tolerant of a broad range of functionalities and can be leveraged toward the scalable synthesis of valuable pharmaceutical scaffolds

  我们在本文中描述了将丝氨酸转化为多种光学纯非天然氨基酸的两步过程。该方法利用溴代烷基中间体和多种芳基卤化物之间的光催化交叉亲电偶联来生产苯丙氨酸、色氨酸和组氨酸的人工类似物。该反应具有广泛的功能，可用于通过流动技术可扩展地合成有价值的药物支架。
• Access to Enantioenriched α-Amino Esters via Rhodium-Catalyzed 1,4-Addition/Enantioselective Protonation
  作者：Laure Navarre、Rémi Martinez、Jean-Pierre Genet、Sylvain Darses

  DOI：10.1021/ja710691p

  日期：2008.5.1

  Conjugate addition of potassium trifluoro(organo)borates 2 to dehydroalanine derivatives 1, mediated by a chiral rhodium catalyst and in situ enantioselective protonation, afforded straightforward access to a variety of protected alpha-amino esters 3 with high yields and enantiomeric excesses up to 95%. Among the tested chiral ligands and proton sources, Binap, in combination with guaiacol (2-methoxyphenol)

  在手性铑催化剂和原位对映选择性质子化的介导下，三氟（有机）硼酸钾 2 与脱氢丙氨酸衍生物 1 的共轭加成可以直接获得各种受保护的 α-氨基酯 3，收率高，对映体过量高达 95% . 在测试的手性配体和质子源中，Binap 与愈创木酚（2-甲氧基苯酚）（一种廉价且无毒的苯酚）结合，提供了最高的不对称诱导。有机锡烷也显示参与该反应。通过对酯部分进行微调，并使用二氟磷作为手性配体，提高了对映选择性，通常接近 95%。氘标记实验揭示，并支持 DFT 计算，
• Stereoselective Synthesis of 3,6-Disubstituted-3,6-dihydropyridin-2-ones as Potential Diketopiperazine Mimetics Using Organocopper-Mediated <i>a</i><i>nti</i>-S_N2‘ Reactions and Their Use in the Preparation of Low-Molecule CXCR4 Antagonists
  作者：Ayumu Niida、Hiroaki Tanigaki、Eriko Inokuchi、Yoshikazu Sasaki、Shinya Oishi、Hiroaki Ohno、Hirokazu Tamamura、Zixuan Wang、Stephen C. Peiper、Kazuo Kitaura、Akira Otaka、Nobutaka Fujii

  DOI：10.1021/jo060390t

  日期：2006.5.1

  Organocopper-mediated anti-SN2‘ reactions of γ-phosphoryloxy-α,β-unsaturated-δ-lactams were used to prepare highly functionalized diketopiperazine mimetics. The substrate phosphates 24, 32, and 47 were prepared from α-amino acid-derived allylic alcohols 10 by a sequence of reactions that included ring-closing metathesis. In the reactions of phosphates with organocopper reagents, the addition of LiCl

  使用有机铜介导的γ-磷酰氧基-α，β-不饱和-δ-内酰胺的抗-S N 2'反应制备高度功能化的二酮哌嗪模拟物。基板磷酸盐24，32，和47从α氨基酸衍生的烯丙醇制备10通过反应，包括闭环复分解的序列。在磷酸盐与有机铜试剂的反应中，添加LiCl可以显着改善抗S N2'选择性，表明含有氯化锂的有机铜簇在确定区域选择性中起重要作用。该反应体系用于制备新型低分子量CXCR4-趋化因子受体拮抗剂。
• Nickel-Catalyzed Reductive Cross-Coupling of Aryl Triflates and Nonaflates with Alkyl Iodides
  作者：Yuto Sumida、Takamitsu Hosoya、Tomoe Sumida

  DOI：10.1055/s-0036-1588464

  日期：2017.8

  coupling of aryl triflates and nonaflates with alkyl iodides using manganese(0) as a reductant is described. The method is applicable to the reductive alkylation of various aryl sulfonates, including o-borylaryl triflate, which enabled efficient construction of diverse alkylated arenes under mild conditions. A nickel-catalyzed cross-electrophile coupling of aryl triflates and nonaflates with alkyl iodides

  致力于向山辉明教授在他90的庆祝日生日（Sotsuju） 发布时间为专题的一部分高级策略合成镍 抽象的 描述了使用锰（0）作为还原剂的芳基三氟甲磺酸酯和壬酸酯与烷基碘的镍催化交叉亲电子偶联。该方法适用于各种芳基磺酸盐的还原烷基化，包括三氟甲磺酸邻硼烷基芳基酯，其能够在温和条件下有效地构建各种烷基化的芳烃。 描述了使用锰（0）作为还原剂的芳基三氟甲磺酸酯和壬酸酯与烷基碘的镍催化交叉亲电子偶联。该方法适用于各种芳基磺酸盐的还原烷基化，包括三氟甲磺酸邻硼烷基芳基酯，其能够在温和条件下有效地构建各种烷基化的芳烃。
• Stereoselective Synthesis of [<scp>l</scp>-Arg-<scp>l</scp>/<scp>d</scp>-3-(2-naphthyl)alanine]-Type (<i>E</i>)-Alkene Dipeptide Isosteres and Its Application to the Synthesis and Biological Evaluation of Pseudopeptide Analogues of the CXCR4 Antagonist FC131
  作者：Hirokazu Tamamura、Kenichi Hiramatsu、Satoshi Ueda、Zixuan Wang、Shuichi Kusano、Shigemi Terakubo、John O. Trent、Stephen C. Peiper、Naoki Yamamoto、Hideki Nakashima、Akira Otaka、Nobutaka Fujii

  DOI：10.1021/jm049429h

  日期：2005.1.1

  D-type (E)-alkene dipeptide isosteres (EADIs) that have unnatural side chains at the alpha-position were synthesized by the combination of stereoselective aziridinyl ring-opening reactions and organozinc-copper-mediated anti-S(N)2' reactions toward a single substrate of gamma,delta-cis-gamma,delta-epimino (E)-alpha,beta-enoate. The utility of this methodology was demonstrated by the stereoselective synthesis

  通过立体选择性氮丙啶基开环反应和有机锌-铜介导的抗氧化剂的结合，合成了在α-位具有非天然侧链的L，L-型和L，D-型（E）-烯烃二肽等排体（EADIs）。 -S（N）2'反应朝向单个底物的伽玛，δ-顺式-γ，δ-表皮（E）-α，β-烯酸酯。此方法的实用性通过立体选择性合成L-Arg-L / D-3-（2-萘基）丙氨酸（Nal）的一组非对映体EADI组成，该化合物包含在一个小的CXCR4拮抗剂FC131 [环（- D-Tyr-Arg-Arg-Nal-Gly-）]。此外，（Nal-Gly）型EADI是由二碘化sa（SmI（2））诱导的γ-乙酰氧基-α，β-烯酸酯的还原反应合成的。几个FC131类似物，其中插入了这些EADI以降低其肽的特性，