2-amino-3-[dimethyl(phenyl)silyl]propionic acid | 197378-99-7

• 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: 2-amino-3-[dimethyl(phenyl)silyl]propionic acid
• 英文别名: 2-Amino-3-[dimethyl(phenyl)silyl]propanoic acid
• CAS: 197378-99-7
• 化学式: C₁₁H₁₇NO₂Si
• 分子量: 223.347
• InChiKey: NUJKJRUPWGDRHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.01
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  potassium cyanate 、 2-amino-3-[dimethyl(phenyl)silyl]propionic acid 在 吡啶 、 盐酸 、 溶剂黄146 作用下， 生成 DL-2-carbamoylamino-3-[(dimethyl)phenylsilyl]propionic acid
  参考文献：
  名称：

  含硅的α-氨基酸和乙内酰脲的合成

  摘要：

  已经以外消旋形式制备了三种新的含硅的α-氨基酸6a-c和它们各自的乙内酰脲衍生物8a-c。α-氨基氰乙酸酯衍生物与碘甲基取代的硅烷烷基化，然后水解得到氨基酸，随后与KOCN和与HCl的反应得到乙内酰脲。乙内酰脲计划进行生物技术脱硝处理。

  DOI：

  10.1016/s0040-4020(97)00887-9
• 作为产物：
  描述：

  二甲基氯甲基苯基硅烷 在 lithium hydroxide 、 正丁基锂 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 反应 16.25h， 生成 2-amino-3-[dimethyl(phenyl)silyl]propionic acid
  参考文献：
  名称：

  Syntheses of racemic and non-racemic silicon- and germanium-containing α-amino acids of the formula type H2NCH(CH2ElR3)COOH (El=Si, Ge; R=organyl) and incorporation of d-H2NCH(CH2SiMe3)COOH and d-H2NCH(CH2GeMe3)COOH into biologically active decapeptides: a study on C/Si/Ge bioisosterism

  摘要：

  Two novel efficient methods for the synthesis of racemic silicon- and germanium-containing a-amino acids of the formula type rac-H2NCH(CH2EIR3)COOH (El = Si, Ge; R = organyl), starting from 3,6-diethoxy-2,5-dihydropyrazine, have been developed. Racemic cc-amino acids synthesized: rac-H2NCH(CH2SiMe3)COOH (rac-2), rac-H2NCH(CH2GeMe3)COOH (rac-3), rac-H2NCH(CH2SiMe2Ph)COOH (rac-4), rac-H2NCH(CH2GeMe2Ph)COOH (rac-5), and rac-H2NCH(CH2SiMe2CH=CH2)COOH (rac-6). Preparative liquid-chromatographic resolution of rac-2 and rac-3 [CHIROBIOTIC T (glycopeptide Teicoplanin covalently linked to spherical silica gel) as the stationary phase] yielded the alpha -amino acids (R)-2, (S)-2, (R)-3, and (S)-3. The (R)- and (S)-enantiomers of beta-(trimethylsilyl)alanine [(R)- and (S)-2] and beta-(trimethylgermyl)alanine I(R)- and (S)-3] are sila-analogs and germa-analogs, respectively, of the antipodes of the non-proteinogenic alpha -amino acid beta -tert-butylalanine [(S)- and (R)-H2NCH(CH2CMe3)COOH; (S)- and (R)-1]. Starting from the N-Fmoc-protected C/Si/Ge-analogous (D-configurated) alpha -amino acids (R)-1, (S)-2, and (S)-3, the C/Si/Ge-analogous decapeptides 7-9 [Ac-D-Nal(1)-4-Cl-D-Phe(2)-D-Pal(3)-Ser(4)-N-Me-Tyr(5)-D-Hci(6)- Nle(7)-Arg(8)-Pro(9)-D-Me(3)El-Ala(10)-NH2 (7, El = C; 8, El = Si; 9, El = Ge)] were prepared by sequential solid-phase synthesis. The decapeptides 7-9 were studied in vitro in a functional assay using a recombinant cell line expressing the human GnRH receptor (agonist Triptorelin). Compounds 7-9 behaved as medium-potent GnRH antagonists, the antagonistic potencies of these three C/Si/Ge analogs being very similar. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(01)00783-5

文献信息

• Synthesis of β-Silyl α-Amino Acids via Visible-Light-Mediated Hydrosilylation
  作者：Yi Wan、Jiajie Zhu、Qiyang Yuan、Wei Wang、Yongqiang Zhang

  DOI：10.1021/acs.orglett.1c00065

  日期：2021.2.19

  of β-silyl α-amino acids is reported via the application of visible-light-mediated hydrosilylation. The reaction utilizes readily accessible and structurally diverse hydrosilanes to provide radicals for conjugate addition to dehydroalanine ester and analogues. Notably, the use of chiral methyleneoxazolidinone as the substrate and chiral inducer enabled the highly stereoselective synthesis. Furthermore

  据报道，通过应用可见光介导的氢化硅烷化，可以方便地合成 β-甲硅烷基 α-氨基酸。该反应利用易于获得且结构多样的氢硅烷来提供自由基，用于与脱氢丙氨酸酯和类似物进行共轭加成。值得注意的是，使用手性亚甲基恶唑烷酮作为底物和手性诱导剂实现了高度立体选择性合成。此外，该反应还可以以连续流动的方式进行并放大到克级。