(alphaS)-alpha-(乙酰氨基)-苯乙酸甲酯 | 36060-84-1

• 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
• 中文名称: (alphaS)-alpha-(乙酰氨基)-苯乙酸甲酯
• 英文名称: (S)-Acetamide of phenylglycine methylester
• 英文别名: (S)-N-acetyl-phenylglycine methyl ester；methyl (S)-N-acetylphenylglycinate；N-acetyl-Phg-OMe；(S)-Methyl 2-acetamido-2-phenylacetate；methyl (2S)-2-acetamido-2-phenylacetate
• CAS: 36060-84-1
• 化学式: C₁₁H₁₃NO₃
• 分子量: 207.229
• InChiKey: SAPRVTLHJXZROQ-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  (alphaS)-alpha-(乙酰氨基)-苯乙酸甲酯 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以85%的产率得到L-(+)-N-Ac-phenylglycine hydrazide
  参考文献：
  名称：

  从对映体苯基甘氨酸酰肼高效合成新的2-氨基甲基-1,3,4-恶二唑

  摘要：

  在冰乙酸的存在下，在N-保护的苯基甘氨酸酰肼与原酸三乙酯（原甲酸，原乙酸，原丙酸，原苯甲酸酯）的反应中合成了2-氨基甲基-1,3,4-恶二唑的新衍生物。研究了对酸敏感的裂解反应Ñ -BOC和Ñ被-Ac 1,3,4-恶二唑呈现。分光特性小号的化合物和试图阐明产品中观察到的现象消旋的进行了讨论。

  DOI：

  10.1016/j.tet.2008.11.096
• 作为产物：
  描述：

  (Z)-2-乙酰氨基-3-苯基丙烯酸甲酯 在 norborna-2,5-diene(S,S-1,2-bis(2,5-diethylphospholanyl)benzene)rhodium(I) tetrafluoroborate 氢气 作用下， 以 乙醇 为溶剂， 26.0 ℃ 、300.0 kPa 条件下， 生成 (alphaS)-alpha-(乙酰氨基)-苯乙酸甲酯
  参考文献：
  名称：

  On the economic application of DuPHOS rhodium(I) catalysts: a comparison of COD versus NBD precatalysts

  摘要：

  The effectiveness of cyclooctadiene and norbornadiene precatalysts of the type [Rh(DuPHOS)(diolefin)]BF4 in catalytic asymmetric hydrogenation of various prochiral olefins has been examined. In some of the systems studied, the NBD complex gave rise to the catalytically active species more rapidly than the corresponding COD complex, as expected. However, as catalyst loadings were reduced to levels more conducive to economic manufacture, the difference between the use of COD and NBD precatalysts became increasingly insignificant. This was conveniently highlighted by the formation of low enantiomeric excess products upon using an equimolar mixture of (S,S) and (R,R) precatalysts, bearing COD and NBD respectively. With other substrates, the system displayed no induction time for either precatalyst and identical reaction profiles were observed. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01552-0

文献信息

• <i>Carica papaya</i>Lipase Catalysed Resolution of β-Amino Esters for the Highly Enantioselective Synthesis of (<i>S</i>)-Dapoxetine
  作者：Pengyong You、Jian Qiu、Erzheng Su、Dongzhi Wei

  DOI：10.1002/ejoc.201201055

  日期：2013.1

  CPL-catalysed resolution. The mechanism of the CPL-catalysed enantioselective alcoholoysis of the amino acids is discussed to delineate the substrate requirements for CPL-catalysed resolution. Finally, the reaction was scaled up, and the products were separated and obtained in good yields (≥ 80 %). The (S)-3-amino-3-phenylpropanoic acid obtained was used as a key chiral intermediate in the synthesis

  通过番木瓜脂肪酶 (CPL) 催化对映选择性醇解相应的外消旋 N 保护的 2,2,2-三氟乙酯在有机溶剂中的有效合成（S）-3-氨基-3-苯基丙酸对映​​体. 高对映选择性（E > 200）通过两种策略实现，涉及底物工程和反应条件的优化。基于一系列氨基酸的拆分，发现底物的结构对CPL催化的拆分具有深远的影响。通过将常规甲酯转换为活化的三氟乙酯，显着提高了对映选择性和反应速率。在考虑空间效应时，取代的苯基和氨基对于 CPL 催化的拆分不应都很大。讨论了 CPL 催化的氨基酸对映选择性醇解的机制，以描述 CPL 催化拆分的底物要求。最后，放大反应，分离产物并以良好的收率（≥ 80 %）获得。获得的 (S)-3-氨基-3-苯基丙酸用作合成 (S)-达泊西汀的关键手性中间体，对映体过量 (> 99 %)。
• Heterocyclic inhibitors of ERK2 and uses thereof
  申请人：Cao Jingrong

  公开号：US20070265263A1

  公开（公告）日：2007-11-15

  Described herein are compounds that are useful as protein kinase inhibitors having the formula: wherein Z 1 and Z 2 are each independently nitrogen or CH and Ring A, T m R 1 , QR 2 , U n R 3 , and Sp are as described in the specification. The compounds are especially useful as inhibitors of ERK2 and for treating diseases in mammals that are alleviated by a protein kinase inhibitor, particularly diseases such as cancer, inflammatory disorders, restenosis, diabetes, and cardiovascular disease.

  本文介绍了一些具有下列式的蛋白激酶抑制剂的化合物： 其中Z1和Z2各自独立地为氮或CH，环A、TmR1、QR2、UnR3和Sp如说明书所述。这些化合物特别适用于抑制ERK2并治疗哺乳动物中由蛋白激酶抑制剂缓解的疾病，特别是癌症、炎症性疾病、再狭窄、糖尿病和心血管疾病等疾病。
• Sulfonamides
  申请人：Crosignani Stefano

  公开号：US20110028509A1

  公开（公告）日：2011-02-03

  The invention relates to compounds of formula I wherein R 1 , R 2 , R 4 , R a , R b , R c , R e , A*, W 1 , W 2 and W 3 are as defined in claim 16 , for the treatment of CXCR3 related diseases.

  该发明涉及式I的化合物，其中R1、R2、R4、Ra、Rb、Rc、Re、A*、W1、W2和W3的定义如权利要求16所述，用于治疗与CXCR3相关的疾病。
• Chiral 1,2,4-triazoles: stereoselective acylation and chlorination
  作者：Alan R. Katritzky、Dmytro Fedoseyenko、Myong S. Kim、Peter J. Steel

  DOI：10.1016/j.tetasy.2009.12.007

  日期：2010.1

  Acyl groups are transferred from diverse N- and O-acyl derivatives of chiral 3.5-bis-(1-hydroxyethyl)-[ 1,2,4]-triazole to amino acid esters enantioselectively, with 7% to 68% ee. depending on the temperature conditions and nature of the reagents Thionyl chloride replaced the hydroxyl groups of (S)-1-[4-amino5-((S)- 1-hydroxy-ethyl)-[1,2,4]-triazol-3-yl]-ethanol 3 stereospecifically with inversion, as confirmed by X-ray analysis, which also revealed unusual crystal structures with asymmetric units comprising three molecules of 4-amino-3,5-bis(R-1-chloroethyl)-1,2,4-triazole 5 and four of 3,5-bis((R)-1-chloroethyl)-1H-1,2,4-triazole 6. (c) 2010 Elsevier Ltd All rights reserved
• Rational de novo design of NADH mimic for stereoselective reduction based on molecular orbital calculation
  作者：Tadashi Eguchi、Miki Fukuda、Yumiko Toyooka、Katsumi Kakinuma

  DOI：10.1016/s0040-4020(97)10294-0

  日期：1998.1

  The methodology of rational design of NADH mimics in stereoselective reduction of carbonyl and imino groups based on molecular orbital calculation was described. The designed NADH mimics la and Ib were subjected to the reduction of benzoylformate and acetyliminophenylacetate. As expected from the calculations of the transition-states, the reduction with la proceeded with high stereoselectivity in both substrates, while Ib showed much lower chirality transfer. (C) 1997 Elsevier Science Ltd. All rights reserved.