isopropyl (R)-2-tert-butoxycarbonylamino-3-phenylpropanoate | 1026133-82-3

• 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: isopropyl (R)-2-tert-butoxycarbonylamino-3-phenylpropanoate
• 英文别名: (R)-isopropyl 2-tert-butoxycarbonylamino-3-phenylpropanoate；isopropyl (tert-butoxycarbonyl)-phenylalaninate；Boc-Phe-OiPr；propan-2-yl (2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoate
• CAS: 1026133-82-3
• 化学式: C₁₇H₂₅NO₄
• 分子量: 307.39
• InChiKey: JZMMVTPQJGFDMV-CQSZACIVSA-N

物化性质

• 熔点：
  93 °C
• 沸点：
  424.7±38.0 °C(Predicted)
• 密度：
  1.069±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  isopropyl (R)-2-tert-butoxycarbonylamino-3-phenylpropanoate 在 盐酸 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 2.17h， 生成 C₁₃H₁₅NO₃
  参考文献：
  名称：

  Enantiomeric recognition of carboxylic anions by a library of neutral receptors derived from α-amino acids and o-phenylenediamine

  摘要：

  A library of eight neutral anion receptors consisting of a-amino acid esters attached to o-phenylenediamine by urea groups was synthesized and analysed in terms of capacity for chiral recognition of carboxylates. The NMR titrations revealed that the association constants of complexes consisting of a chiral guest and a chiral host are two orders of magnitude lower than those of achiral partners. Diverse substituents in the receptor structure modify both the affinities and enantioselectivities. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.06.004
• 作为产物：
  描述：

  Boc-D-苯丙氨酸 、 异丙醇 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以64%的产率得到isopropyl (R)-2-tert-butoxycarbonylamino-3-phenylpropanoate
  参考文献：
  名称：

  Enantiomeric recognition of carboxylic anions by a library of neutral receptors derived from α-amino acids and o-phenylenediamine

  摘要：

  A library of eight neutral anion receptors consisting of a-amino acid esters attached to o-phenylenediamine by urea groups was synthesized and analysed in terms of capacity for chiral recognition of carboxylates. The NMR titrations revealed that the association constants of complexes consisting of a chiral guest and a chiral host are two orders of magnitude lower than those of achiral partners. Diverse substituents in the receptor structure modify both the affinities and enantioselectivities. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.06.004

文献信息

• 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，
• Asymmetric Synthesis of Functionalized Phenylalanine Derivatives via Rh-Catalyzed Conjugate Addition and Enantioselective Protonation Cascade
  作者：Jia-Hong Jian、Hao-Wei Zeng、Ting-Shen Kuo、Ping-Yu Wu、Hsyueh-Liang Wu

  DOI：10.1021/acs.orglett.9b03666

  日期：2019.12.6

  The asymmetric conjugate addition of arylboronic acids to N-phthalimidodehydroalanine 1i catalyzed by Rh(I)/L1a enables the facile preparation of chiral functionalized phenylalanines. The reaction proceeds by a conjugate addition and enantioselective protonation cascade, affording a rhodium enolate that undergoes re-face protonation. The reaction tolerates various arylboronic acids and can be used

  Rh（I）/ L1a催化将芳基硼酸不对称共轭加成到N-邻苯二甲酰亚胺脱氢丙氨酸1i上，可以轻松制备手性官能化的苯丙氨酸。通过共轭加成和对映选择性的质子化级联反应的进行，得到铑烯醇化物经历重新面取向质子化。该反应可耐受各种芳基硼酸，可用于克级合成（S）-苯丙氨酸盐酸盐，证明了反应范围和该方法的合成可行性。
• PROCESS FOR PREPARING CHIRAL AMINO ACIDS
  申请人：Darses Sylvain

  公开号：US20140012005A1

  公开（公告）日：2014-01-09

  The present invention relates to a process for preparing chiral amino acids with excellent enantiomeric excesses.

  本发明涉及一种制备具有优异对映体过量的手性氨基酸的方法。
• Enantiomeric recognition of carboxylic anions by a library of neutral receptors derived from α-amino acids and o-phenylenediamine
  作者：Filip Ulatowski、Janusz Jurczak

  DOI：10.1016/j.tetasy.2014.06.004

  日期：2014.7

  A library of eight neutral anion receptors consisting of a-amino acid esters attached to o-phenylenediamine by urea groups was synthesized and analysed in terms of capacity for chiral recognition of carboxylates. The NMR titrations revealed that the association constants of complexes consisting of a chiral guest and a chiral host are two orders of magnitude lower than those of achiral partners. Diverse substituents in the receptor structure modify both the affinities and enantioselectivities. (C) 2014 Elsevier Ltd. All rights reserved.