(S)-N,N,O-tribenzylallylglycine | 874384-01-7

• 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: (S)-N,N,O-tribenzylallylglycine
• 英文别名: benzyl (S)-2-(dibenzylamino)pent-4-enoate；(S)-benzyl N,N-dibenzyl allylglycinate；(S)-benzyl N,N-dibenzylallylglycine；benzyl (2S)-2-(dibenzylamino)pent-4-enoate
• CAS: 874384-01-7
• 化学式: C₂₆H₂₇NO₂
• 分子量: 385.506
• InChiKey: CYVPFUORUTYJKM-VWLOTQADSA-N

物化性质

• 沸点：
  486.2±45.0 °C(Predicted)
• 密度：
  1.104±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-N,N,O-tribenzylallylglycine 在 三(三苯基膦)羰基氢化铑 、 palladium dihydroxide 氢气 、 N,N-二异丙基乙胺 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 lithium chloride 作用下， 以 甲醇 、 甲苯 、 乙腈 为溶剂， 20.0~40.0 ℃ 、2.03 MPa 条件下， 反应 180.0h， 生成 (2S)-2-氨基-8-氧代癸酸
  参考文献：
  名称：

  Synthesis of 2-Amino-8-oxodecanoic Acids (Aodas) Present in Natural Hystone Deacetylase Inhibitors

  摘要：

  Differently substituted 2-amino-8-oxodecanoic acids (Aodas), present in naturally occurring inhibitors of hystone deacetylase (HDAC), have been prepared using a convergent approach. The configuration in position 2 was derived from enantiomerically pure allylglycine or glutamic acid, whereas the stereochemistry of the substituent in position 9 derived from lactic acid or glyceraldehyde derivatives. Starting from allylglycine, (S)-Aodas, protected at the nitrogen as Boc or Fmoc, were obtained in four steps in about 30% overall yield. These products have been used to prepare a simplified analogue of a natural cyclic tetrapeptide HDAC inhibitor by SPPS.

  DOI：

  10.1021/jo0518250
• 作为产物：
  描述：

  (S)-(-)-2-氨基-4-戊烯酸 、 溴甲苯 在 sodium carbonate 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 2.0h， 以67%的产率得到(S)-N,N,O-tribenzylallylglycine
  参考文献：
  名称：

  非对映选择性和支链醛选择性串联加氢甲酰化-半缩醛形成：官能化哌啶和氨基醇的合成

  摘要：

  从容易获得的烯丙基甘氨酸开始，已开发出串联加氢甲酰化-半胱氨酸形成反应，用于合成手性官能化哌啶，使用Rh /（S，S，S）-BOBPHOS催化剂具有非常好的非对映选择性和支链区域选择性。串联加氢甲酰化-半缩醛的形成也具有良好的非对映选择性（88:12），半缩醛产物被氢化并保留了立体化学，从而提供了一种手性中间体，用于合成新的抗生素奈诺沙星。

  DOI：

  10.1021/acs.orglett.7b01049

文献信息

• Manganese Catalyzed Hydrogenation of Enantiomerically Pure Esters
  作者：Magnus B. Widegren、Matthew L. Clarke

  DOI：10.1021/acs.orglett.8b00864

  日期：2018.5.4

  A manganese-catalyzed hydrogenation of esters has been accomplished with TONs up to 1000, using cheap, environmentally benign, potassium carbonate and simple alcohols as activator and solvent, respectively. The weakly basic conditions lead to good functional group tolerance and enable the hydrogenation of enantiomerically enriched α-chiral esters with essentially no loss of stereochemical integrity

  锰的酯催化氢化反应已完成，TONs的用量高达1000，分别使用廉价，对环境无害的碳酸钾和简单的醇作为活化剂和溶剂。弱碱性条件导致良好的官能团耐受性，并能够氢化对映异构体富集的α-手性酯，而基本上不损失立体化学完整性。
• [EN] MANGANESE-CATALYSED HYDROGENATION OF ESTERS<br/>[FR] HYDROGÉNATION D'ESTERS CATALYSÉE PAR DU MANGANÈSE
  申请人：UNIV COURT UNIV ST ANDREWS

  公开号：WO2019138216A1

  公开（公告）日：2019-07-18

  The present invention relates to the field of catalytic hydrogenation and, more particularly, to methods of manganese-catalysed hydrogenation of esters to alcohols. Advantageously, where the esters are chiral, the hydrogenations proceed with high or complete stereochemical integrity..

  本发明涉及催化加氢领域，更具体地涉及锰催化酯类化合物加氢生成醇的方法。优点是，当酯类化合物是手性的时，加氢反应可以高效地或完全地保持立体化学完整性。
• Microwave assisted hydroaminomethylation of alkenes
  作者：Elena Petricci、André Mann、Jessica Salvadori、Maurizio Taddei

  DOI：10.1016/j.tetlet.2007.09.154

  日期：2007.11

  Hydroaminomethylation of terminal alkenes can be regioselectively carried out in less than 30 min with secondary amines in EtOH under MW irradiation using (PPh3)(3)RhCO(H) and Xantphos or Biphephos as ligands. When primary amines were employed, the corresponding enamines were obtained in good yields. Tris-benzyl allylglycine was transformed into different (basic) benzylated a-amino acids. Moreover, the benzyl protection was removed in few minutes under MW irradiation with Pd(OH)(2) under H-2 atmosphere. (c) 2007 Elsevier Ltd. All rights reserved.
• MANGANESE-CATALYSED HYDROGENATION OF ESTERS
  申请人：University Court of the University of St Andrews

  公开号：US20210053932A1

  公开（公告）日：2021-02-25

  The present invention relates to the field of catalytic hydrogenation and, more particularly, to methods of manganese-catalysed hydrogenation of esters to alcohols. Advantageously, where the esters are chiral, the hydrogenations proceed with high or complete stereochemical integrity.
• Synthesis of 2-Amino-8-oxodecanoic Acids (Aodas) Present in Natural Hystone Deacetylase Inhibitors
  作者：Manuela Rodriquez、Ines Bruno、Elena Cini、Mauro Marchetti、Maurizio Taddei、Luigi Gomez-Paloma

  DOI：10.1021/jo0518250

  日期：2006.1.1

  Differently substituted 2-amino-8-oxodecanoic acids (Aodas), present in naturally occurring inhibitors of hystone deacetylase (HDAC), have been prepared using a convergent approach. The configuration in position 2 was derived from enantiomerically pure allylglycine or glutamic acid, whereas the stereochemistry of the substituent in position 9 derived from lactic acid or glyceraldehyde derivatives. Starting from allylglycine, (S)-Aodas, protected at the nitrogen as Boc or Fmoc, were obtained in four steps in about 30% overall yield. These products have been used to prepare a simplified analogue of a natural cyclic tetrapeptide HDAC inhibitor by SPPS.