(S)-2-allyl-2-phenylglycine t-butyl ester | 848829-60-7

• 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)-2-allyl-2-phenylglycine t-butyl ester
• 英文别名: tert-butyl (2S)-2-amino-2-phenylpent-4-enoate
• CAS: 848829-60-7
• 化学式: C₁₅H₂₁NO₂
• 分子量: 247.337
• InChiKey: YLUVUPDTZWWPDZ-HNNXBMFYSA-N

物化性质

• 沸点：
  317.3±30.0 °C(Predicted)
• 密度：
  1.026±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-allyl-2-phenylglycine t-butyl ester 在 N,N,N',N'-四甲基-1,6-己二胺 、 溴 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.08h， 生成 N-((3S,5R)-5-Bromomethyl-2-oxo-3-phenyl-tetrahydro-furan-3-yl)-4-methyl-benzenesulfonamide
  参考文献：
  名称：

  Stereoselective synthesis of 4-hydroxy-2-phenylproline framework

  摘要：

  Highly diastercoselective (>20:1) bromo-lactonization of N-sulfonyl-2-allyl-2-phenylglycine methyl ester (11) was observed. Successive treatment of the chiral lactone with MeONa gave the desired (2S,4R)-4-hydroxy-2-phenylproline derivative in high yield without erosion of the diastereoselectivity. The starting chiral non-racemic compound (5) was prepared from the racemic 2-phenylglycine using a classical kinetic resolution (crystallization), an asymmetric phase transfer alkylation, and an enzyme-catalyzed kinetic resolution. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.12.130
• 作为产物：
  描述：

  (S)-2-{[1-(4-Chloro-phenyl)-meth-(E)-ylidene]-amino}-2-phenyl-pent-4-enoic acid tert-butyl ester 在 柠檬酸 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-2-allyl-2-phenylglycine t-butyl ester
  参考文献：
  名称：

  厌氧条件在手性相转移催化高对映选择性合成α,α-二烷基-α-氨基酸中的优势

  摘要：

  在有氧条件下，对受保护δ-氨基酸衍生物催化不对称相转移烷基化过程中的烯醇氧化进行了干预，并引入了厌氧条件，以获得令人满意的合成化学产率和高水平的对映选择性。

  DOI：

  10.1055/s-2001-15167

文献信息

• Phase-Transfer-Catalyzed Asymmetric S_NAr Reaction of α-Amino Acid Derivatives with Arene Chromium Complexes
  作者：Seiji Shirakawa、Kenichiro Yamamoto、Keiji Maruoka

  DOI：10.1002/anie.201409065

  日期：2015.1.12

  zed asymmetric SNAr reactions provide unique contribution to the catalytic asymmetric α‐arylations of carbonyl compounds to produce biologically active α‐aryl carbonyl compounds, the electrophiles were limited to arenes bearing strong electron‐withdrawing groups, such as a nitro group. To overcome this limitation, we examined the asymmetric SNAr reactions of α‐amino acid derivatives with arene chromium

  尽管相转移催化的不对称S N Ar反应为羰基化合物的催化不对称α-芳基化反应产生了生物活性的α-芳基羰基化合物做出了独特贡献，但亲电试剂仅限于带有强吸电子基团的芳烃，例如硝基。为了克服这一局限性，我们研究了α-氨基酸衍生物与衍生自氟代芳烃的芳烃铬配合物（包括含给电子取代基的芳烃铬配合物）的不对称S N Ar反应。联萘改性的手性相转移催化剂可有效地促进芳基化反应，从而生成相应的α，α-二取代的α-氨基酸，其中包含具有高对映选择性的各种芳族取代基。
• Stereoselective synthesis of 4-hydroxy-2-phenylproline framework
  作者：Kenji Maeda、Ross A. Miller、Ronald H. Szumigala、Ali Shafiee、Sandor Karady、Joseph D. Armstrong

  DOI：10.1016/j.tetlet.2004.12.130

  日期：2005.2

  Highly diastercoselective (>20:1) bromo-lactonization of N-sulfonyl-2-allyl-2-phenylglycine methyl ester (11) was observed. Successive treatment of the chiral lactone with MeONa gave the desired (2S,4R)-4-hydroxy-2-phenylproline derivative in high yield without erosion of the diastereoselectivity. The starting chiral non-racemic compound (5) was prepared from the racemic 2-phenylglycine using a classical kinetic resolution (crystallization), an asymmetric phase transfer alkylation, and an enzyme-catalyzed kinetic resolution. (C) 2005 Elsevier Ltd. All rights reserved.
• Advantage of Anaerobic Conditions in the Highly Enantioselective Synthesis of α,α-Dialkyl-α-Amino Acids by Chiral Phase-Transfer Catalysis
  作者：Takashi Ooi、Mifune Takeuchi、Daisuke Ohara、Keiji Maruoka

  DOI：10.1055/s-2001-15167

  日期：——

  Intervention of the enolate oxidation in the catalytic asymmetric phase-transfer alkylation of protected α-amino acid derivatives under aerobic conditions has been addressed, and anaerobic conditions have been introduced to obtain synthetically satisfactory chemical yields as well as a high level of enantioselectivity.

  在有氧条件下，对受保护δ-氨基酸衍生物催化不对称相转移烷基化过程中的烯醇氧化进行了干预，并引入了厌氧条件，以获得令人满意的合成化学产率和高水平的对映选择性。