(R)-2-Phenylbutyric anhydride

• 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: (R)-2-Phenylbutyric anhydride
• 英文别名: [(2R)-2-phenylbutanoyl] (2R)-2-phenylbutanoate
• 化学式: C₂₀H₂₂O₃
• 分子量: 310.393
• InChiKey: NMVCQWBTTHDUQD-QZTJIDSGSA-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 、 (R)-2-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

文献信息

• 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。
• Stereochemical effects in mass spectrometry. 7. Determination of absolute configuration of some organic molecules by reaction mass spectrometry
  作者：Yao-Zu Chen、Hung Li、Hou-Jun Yang、Su-Ming Hua、Hai-Quan Li、Fan-Zhi Zhao、Nen-Yu Chen

  DOI：10.1002/oms.1210231205

  日期：1988.12

  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.