(S,S)-α-Phenylbutyric anhydride | 16906-38-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S,S)-α-Phenylbutyric anhydride
• 英文别名: S(+)-Phenylbuttersaeureanhydrid；(S)-2-phenylbutyric anhydride；S-2-phenylbutyric anhydride；[(2S)-2-phenylbutanoyl] (2S)-2-phenylbutanoate
• CAS: 16906-38-0
• 化学式: C₂₀H₂₂O₃
• 分子量: 310.393
• InChiKey: NMVCQWBTTHDUQD-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2S)-2-甲氨基-1-苯基丙-1-醇 、 (S,S)-α-Phenylbutyric anhydride 生成
  参考文献：
  名称：

  Stereochemical effects in mass spectrometry. 7. Determination of absolute configuration of some organic molecules by reaction mass spectrometry

  摘要：

  AbstractIt was found that in the chemical ionization (isobutane) mass spectra of some asymmetric secondary alcohols and α‐amino acids, when a pair of enantiomers (such as R‐ and S‐2‐phenyIbutyric anhydride, R‐ and S‐mandelic acid, R‐ and S‐2‐methylbutanoic acid or R‐ and S‐α‐phenyl ethyl amine) were used as reaction reagents, the relative abundances of characteristic ions formed by the stereoselective reaction between sample and reagent of the same configuration were much higher than those ions formed by the sample and a reagent of a different configuration. The absolute configuration of the sample molecule may be predicted by examination of mass spectra of the sample measured with R‐ and S‐reagent respectively. This approach proved to be a convenient way for determination of the absolute configurations of organic molecules on a micromole level by mass Spectrometry.

  DOI：

  10.1002/oms.1210231205
• 作为产物：
  描述：

  S(+)-2-苯基丁酸 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到(S,S)-α-Phenylbutyric anhydride
  参考文献：
  名称：

  A method for determining the enantiomeric purity of profens

  摘要：

  A simple method for determining the enantiomeric purity of profens (based on the carbon skeleton of 2-phenylpropionic acid) is discussed. The enantiomeric purity of a given profen can be determined by stereospecific DCC self-coupling to give a statistical diastereoisomeric mixture of racemic and meso- anhydrides. The relative ratio of diastereoisomers formed can be related to the enantiomeric excess of the original carboxylic acid. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.051

文献信息

• A Basic Study of the Amino Acid Residue in Protein. The Role of Hydrocarbon Groups in Enantiomer-differentiating Acylation
  作者：Yuji Hiraki、Akira Tai

  DOI：10.1246/bcsj.57.1570

  日期：1984.6

  The enantiomer-differentiating acylation (kinetic resolution) of 1-phenylalkylamines and their derivatives was carried out with (S)-2-phenylbutyric anhydride and its derivatives in aqueous and nonaqueous media. On the basis of the distributions of the two diastereomeric products, the molecular interactions between hydrocarbon residues responsible for the structural recognition of the reacting molecules

  使用 (S)-2-苯基丁酸酐及其衍生物在水性和非水性介质中进行 1-苯基烷基胺及其衍生物的对映异构体差异化酰化（动力学拆分）。根据两种非对映产物的分布，研究了负责反应分子结构识别的烃残基之间的分子相互作用。在非极性介质中，(R,S)-异构体主要形成于 (S,S)-异构体之上。此外，差异主要受底物烷基取代基的大小控制。然而，在水性介质中，主要形成（S，S）-异构体。通过对底物和试剂的环己基类似物的比较研究，结果表明，烷基-苯基和/或苯基-苯基相互作用在识别过程中很重要。将底物分配到试剂相中的过程对于通过悬浮液中的反应来区分对映异构体是无效的。
• Optisch aktive Tetrahydro-diazixanopurine
  作者：Antje Dreier、Rolf Haller

  DOI：10.1002/ardp.198700002

  日期：1987.10

  Optisch aktive Tetrahydro‐diazixanopurine können auf zwei Wegen aus Vorstufen, die über eine Racematspaltung gewonnen worden sind, hergestellt werden. Untersuchungen zur Konfiguration weisen auf eine R‐Konfiguration des Diazixanopurins (+)‐4 hin.

  Optisch aktive Tetrahydro-diazixanopurine können auf zwei Wegen aus Vorstufen, die über eine Racematspaltung gewonnen worden sind, hergestellt werden。Untersuchungen zur Konfiguration weisen auf eine R-Konfiguration des Diazixanopurins (+)-4 hin。
• Antibiotics from Gliding Bacteria, LXXVIII. Ripostatin A, B, and C: Isolation and Structure and Structure Elucidation of Novel Metabolites fromSorangium cellulosum
  作者：Hermann Augustiniak、Gerhard Höfle、Herbert Irschik、Hans Reichenbach

  DOI：10.1002/jlac.199619961026

  日期：1996.10

  Three closely related new metabolites named ripostatins were isolated from the myxobacterium Sorangium cellulosum and their structures elucidated by spectroscopic methods. Two of them, ripostatin A (1a, b) and B (2a), are 14-membered macrolides with an acetic acid and a phenylalkyl side chain, whereas the third metabolite ripostatin C (3a) is an acyclic derivative of ripostatin A. By application of the

  从纤维素粘菌（Sorangium cellulosum）中分离了三种紧密相关的新代谢物，称为ripostatins，并通过光谱法阐明了它们的结构。其中两个是ripostatin A（1a，b）和B（2a）是具有乙酸和苯烷基侧链的14元大环内酯类药物，而第三个代谢产物ripostatin C（3a）是ripostatin A的无环衍生物。应用Helmchen方法的绝对立体化学可以确定为ripostatin A为（11 R，13 R），ripostatin B为11 R，13 S，15 R和11 S通过用13种C标记的前体进料实验揭示了A的聚酮化合物来源，该前体证明了一个分子的苯丙氨酸衍生的苯乙酸，一个丙酸酯单元和十个乙酸单元的掺入。
• Resolution of racemic 12-hydroxyl-1,15-pentadecanlactam using d-glucose derivative as a chiral auxiliary
  作者：Chuan-Jin Hou、Xiao-Mei Liang、Jing-Ping Wu、Jia-Xing Huang、Jian-Jun Zhang、Dao-Quan Wang

  DOI：10.1016/j.tetasy.2008.01.007

  日期：2008.2

  Racemic 12-hydroxyl-1,15-pentadecanlactam 2 was resolved using glucose as a chiral auxiliary for the first time. Both the (R)- and (S)-isomers were obtained in high enantiomeric excesses (>99% by HPLC). The absolute configuration of (+)-2b and (-)-2a was determined by Horeau's method and a modified Mosher's method. (C) 2008 Elsevier Ltd. All rights reserved.
• HIRAKI, YUJI;TAI, AKIRA, CHEM. LETT., 1982, N 3, 341-344
  作者：HIRAKI, YUJI、TAI, AKIRA

  DOI：——

  日期：——