(S)-4-((S)-sec-butyl)oxazolidine-2,5-dione | 45895-90-7

• 物质功能分类: 有机原料 - 酮类化合物
• 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)-4-((S)-sec-butyl)oxazolidine-2,5-dione
• 英文别名: L-Isoleucine N-carboxyanhydride；(4S)-4-[(2S)-butan-2-yl]-1,3-oxazolidine-2,5-dione
• CAS: 45895-90-7
• 化学式: C₇H₁₁NO₃
• 分子量: 157.169
• InChiKey: WAACGCAWLJFFQX-WHFBIAKZSA-N

物化性质

• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-4-((S)-sec-butyl)oxazolidine-2,5-dione 在 三乙胺 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 生成 NPS-Ile-Glyc
  参考文献：
  名称：

  Kricheldorf,H.R.; Fehrle,M., Chemische Berichte, 1974, vol. 107, p. 3533 - 3547

  摘要：

  DOI：
• 作为产物：
  描述：

  L-异亮氨酸 在 sodium hydroxide 、 三溴化磷 作用下， 以 乙醚 为溶剂， 生成 (S)-4-((S)-sec-butyl)oxazolidine-2,5-dione
  参考文献：
  名称：

  Friedel-Crafts .alpha.-aminoacylation of alkylbenzene with a chiral N-carboxy-.alpha.-amino acid anhydride without loss of chirality

  摘要：

  A Friedel-Crafts-type alpha-aminoacylation of alkylbenzene with N-carboxy anhydrides Of five L-alpha-amino acids was developed. Five new alpha-aminoalkyl p-methylphenyl ketones and other alpha-aminoalkyl aryl ketones were obtained and isolated as free bases or hydrochloride salts. The chiralities of the original L-alpha-amino acids were retained during this acylation.

  DOI：

  10.1021/jo00052a059

文献信息

• PROCESS FOR PRODUCING AMINO ACID N-CARBOXYANHYDRIDE
  申请人：Fujita Yukihiro

  公开号：US20070015932A1

  公开（公告）日：2007-01-18

  The present invention provides a process for producing an amino acid N-carboxyanhydride, which comprises reacting an amino acid or a derivative thereof with a compound represented by the following formula (1): wherein R 1 and R 2 represent the same or different electron-withdrawing substituents and each independently are an optionally substituted acyl group, an optionally substituted alkyloxycarbonyl group, an optionally substituted perfluoroalkyl group, an optionally substituted perchloroalkyl group, a cyano group, a halogen atom, or a nitro group; and a and b are the same or different and each are an integer of 1-5.

  本发明提供了一种制备氨基酸N-羧酸酐的方法，该方法包括使氨基酸或其衍生物与以下式(1)表示的化合物反应： 其中，R1和R2表示相同或不同的吸电子取代基，各自独立地为可任选取代的酰基、可任选取代的烷氧羰基、可任选取代的全氟烷基、可任选取代的全氯烷基、氰基、卤素原子或硝基；且a和b相同或不同，各自为1至5的整数。
• Revisiting the Juliá–Colonna enantioselective epoxidation: supramolecular catalysis in water
  作者：Christopher Bérubé、Xavier Barbeau、Patrick Lagüe、Normand Voyer

  DOI：10.1039/c7cc01168g

  日期：——

  With only water as solvent, poly-l-leucine serves as supramolecular catalyst for the epoxidation of α,β-unsaturated ketones.

  只用水作为溶剂，聚-亮氨酸作为α，β-不饱和酮的环氧化反应的超分子催化剂。
• The biosynthetic origin of diketopiperazines derived from D-proline
  作者：Steven D. Bull、Stephen G. Davies、Richard M. Parkin、Francisco Sánchez-Sancho

  DOI：10.1039/a802702a

  日期：——

  Investigations reveal that the structures assigned to D-α-amino acid containing diketopiperazines (DKPs) 21–25 isolated from the sponge Calyx CF. podatypa have been reported incorrectly. Synthetic studies and comparison with literature data have enabled the structures of these DKPs to be correctly reassigned. Evidence is presented to suggest that naturally occurring D-Pro-L-Xxx-DKPs are artifacts resulting from non-enzymatic epimerisation of the corresponding L-Pro-L-Xxx-DKP natural products.

  调查显示，从海绵Calyx CF. podatypa中分离出的含D-α-氨基酸的二酮哌嗪（DKPs）21–25所指定的结构被错误报告。合成研究和与文献数据的比较使得这些DKPs的结构得以正确重新分配。证据表明，自然发生的D-Pro-L-Xxx-DKPs是由相应的L-Pro-L-Xxx-DKP天然产物的非酶异构化所产生的伪产物。
• Rapid and Mild Synthesis of Amino Acid <i>N</i> -Carboxy Anhydrides: Basic-to-Acidic Flash Switching in a Microflow Reactor
  作者：Yuma Otake、Hiroyuki Nakamura、Shinichiro Fuse

  DOI：10.1002/anie.201803549

  日期：2018.8.27

  Polymerization of N‐carboxy anhydrides (NCAs) is the primary process used to prepare polypeptides. The synthesis of various pure NCAs is key to the efficient synthesis of polypeptides. The only practical method that can be used to synthesize NCAs requires harsh acidic conditions that make acid‐labile substrates unusable and results in an undesired ring opening of NCAs. Basic‐to‐acidic flash switching

  N的聚合‐羧酸酐（NCA）是用于制备多肽的主要过程。各种纯净NCA的合成是有效合成多肽的关键。唯一可用于合成NCA的实用方法要求苛刻的酸性条件，使酸不稳定的底物无法使用，并导致NCA出现不希望的开环。在微流反应器中使用从碱性到酸性的闪蒸切换和随后的闪蒸稀释技术来演示NCA的合成。它既快速（0.1 s）又温和（20°C），并且包括含有酸不稳定官能团的底物。从基本到酸性的闪光切换既可以加速所需的NCA形成，又可以避免NCA出现不希望的开环。快速稀释排除了酸不稳定官能团的不希望的分解。
• Amino acid and dipeptide derivatives of daunorubicin. 1. Synthesis, physicochemical properties, and lysosomal digestion
  作者：Michele Masquelier、Roger Baurain、Andre Trouet

  DOI：10.1021/jm00185a003

  日期：1980.11

  The synthesis of amino acid and dipeptide derivatives of daunorubicin (DNR) is described. The binding-affinity parameters for DNA of those derivatives were determined by a spectral titration method. The affinity constants of the amino acid and dipeptide derivatives are, respectively, three and ten times lower than that of DNR. The susceptibility of those derivatives toward lysosomal peptidases was

  描述了柔红霉素（DNR）的氨基酸和二肽衍生物的合成。通过光谱滴定法确定那些衍生物的DNA的结合亲和力参数。氨基酸和二肽衍生物的亲和常数分别比DNR低三倍和十倍。研究了那些衍生物对溶酶体肽酶的敏感性。发现Leu和Ala-Leu衍生物被最快地水解成DNR。结论是Leu-DNR和Ala-Leu-DNR可以作为DNR的前药，可以在具有高氨肽酶活性的肿瘤细胞内部或附近激活。