(4R)-2-[2-hydroxyphenyl]-Δ²-1,3-oxazoline-4-carboxylic acid | 155880-11-8

• 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: (4R)-2-[2-hydroxyphenyl]-Δ²-1,3-oxazoline-4-carboxylic acid
• 英文别名: 2-(2'-hydroxyphenyl)-4(R)-oxazolinecarboxylic acid；R-2-(2'-hydroxyphenyl)oxazoline-COOH；(R)-2-(2-Hydroxyphenyl)-4,5-dihydrooxazole-4-carboxylic acid；(4R)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-oxazole-4-carboxylic acid
• CAS: 155880-11-8
• 化学式: C₁₀H₉NO₄
• 分子量: 207.186
• InChiKey: WHVGFDBEOIEPBC-SSDOTTSWSA-N

物化性质

• 沸点：
  447.8±40.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  79.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(2R,3S)-1-[[(3R)-1-[tert-butyl(diphenyl)silyl]oxy-2-oxoazepan-3-yl]amino]-2-methyl-1-oxooctadecan-3-yl] (2R)-6-[formyl(2-trimethylsilylethoxymethoxy)amino]-2-(phenylmethoxycarbonylamino)hexanoate 、 (4R)-2-[2-hydroxyphenyl]-Δ²-1,3-oxazoline-4-carboxylic acid 在 palladium on activated charcoal 氢气 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 [(2R,3S)-1-[[(3R)-1-[tert-butyl(diphenyl)silyl]oxy-2-oxoazepan-3-yl]amino]-2-methyl-1-oxooctadecan-3-yl] (2R)-6-[formyl(2-trimethylsilylethoxymethoxy)amino]-2-[[(4R)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-oxazole-4-carbonyl]amino]hexanoate
  参考文献：
  名称：

  Brasilibactin A的合成及β-羟酸片段的绝对构型的确认

  摘要：

  描述了巴西巴西诺卡氏菌放线菌的细胞毒性铁载体Brasilibactin A和天然产物的三种非天然非对映异构体的合成。通过不对称醛醇缩合反应制备了四种可能的β-羟酸片段的非对映异构体，并用于合成brasilibactin A及其非对映异构体。仔细分析1 H NMR数据证实，brasilibactin A具有17 S，18 R绝对立体化学。

  DOI：

  10.1016/j.tetlet.2007.09.112
• 作为产物：
  描述：

  benzyl 2-(2'-hydroxyphenyl)-4(R)-oxazolinecarboxylate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 (4R)-2-[2-hydroxyphenyl]-Δ²-1,3-oxazoline-4-carboxylic acid
  参考文献：
  名称：

  The Desferrithiocin Pharmacophore

  摘要：

  The (S)-desferrithiocin (DFT) skeleton is shown to be a useful pharmacophore on which to design orally effective iron chelators. While the study clearly indicates that formal reduction of the desazadesmethyldesferrithiocin thiazoline to a thiazolidine (6), expansion of the desmethyldesferrithiocin thiazoline to a thiazine (7), or substitution of the thiazoline sulfur of desazadesmethyldesferrithiocin by an oxygen (8 and 9) lead to a substantial loss of activity, conversion of (S)-desmethyldesferrithiocin (1) to an N-methylhydroxamate (4) or to the hexacoordinate dihydroxamate ligand (5) results in active compounds. This investigation thus demonstrates which structural components of the siderophore are required for iron clearance after oral administration and suggests the use of the desferrithiocin platform as a vector for other chelators.

  DOI：

  10.1021/jm00036a005

文献信息

• Total Synthesis and Biological Evaluation of Transvalencin Z
  作者：Kathryn M. Nelson、Christine E. Salomon、Courtney C. Aldrich

  DOI：10.1021/np200972s

  日期：2012.6.22

  is a natural product from Nocardia transvalensis with relatively potent and selective antimycobacterial activity against Mycobacterium smegmatis, making it an attractive target for structure–activity and mechanism of action studies. The total synthesis of the four possible diastereomers of transvalencin Z was completed (1a–d), and the absolute configurations were defined using chemical synthesis, HPLC

  耐药性结核病的新出现的全球流行病迫切需要确定新的疾病治疗方法。Transvalencin Z ( 1 ) 是来自Nocardia transvalensis的天然产物，对耻垢分枝杆菌具有相对强效和选择性的抗分枝杆菌活性，使其成为结构-活性和作用机制研究的有吸引力的目标。Transvalencin Z的四种可能的非对映异构体的全合成完成（1a - d)，绝对构型是使用化学合成、HPLC 保留时间和旋光度测量定义的。令人惊讶的是，反式瓦伦星 Z 非对映异构体中没有一种对一组微生物病原体表现出任何抑制活性，包括几种分枝杆菌。
• Stereochemical Influence of the Ligand on the Structure of Manganese Complexes:  Implications for Catalytic Epoxidations
  作者：Meenal D. Godbole、Anna C. G. Hotze、Ronald Hage、Allison M. Mills、Huub Kooijman、Anthony L. Spek、Elisabeth Bouwman

  DOI：10.1021/ic051223z

  日期：2005.12.1

  Manganese complexes of the ligand HphoxCOOR (R=H or Me) have been synthesized and characterized by X-ray analysis, ESI-MS, ligand-field spectroscopy, electrochemistry, and paramagnetic 1H NMR. The ligands, chirally pure or racemic, influence the structures of the complexes formed. Manganese(III) complexes of the ligand HphoxCOOMe are square-pyramidal or octahedral with two ligands bound in a trans

  配位体HphoxCOOR（R = H或Me）的锰配合物已经合成，并通过X射线分析，ESI-MS，配体场光谱，电化学和顺磁性1H NMR进行了表征。手性纯的或外消旋的配体影响形成的复合物的结构。配体HphoxCOOMe的锰（III）配合物为正方形-金字塔形或八面体，两个以固态反式结合的配体。外消旋配体（RS-HphoxCOOMe）和对映纯配体（R-HphoxCOOMe）形成具有相似固态结构的锰配合物。ESI-MS和氘代研究证实，溶液中发生配体交换反应，生成内消旋复合物。R-HphoxCOOH的锰（III）配合物为八面体，两个三价阴离子配体以三聚体的方式以fcc-cct方式结合。RS-HphoxCOOH的锰（III）配合物也是八面体，具有两个现在以反义方式反式结合的双阴离子配体，并且两个水分子占据了轴向位点。借助反演-恢复脉冲技术，在弛豫时间的基础上解释了配合物的顺磁性1H NMR光谱。咪唑与
• Syntheses and studies of amamistatin B analogs reveals that anticancer activity is relatively independent of stereochemistry, ester or amide linkage and select replacement of one of the metal chelating groups
  作者：Chunrui Wu、Patricia A. Miller、Marvin J. Miller

  DOI：10.1016/j.bmcl.2011.01.084

  日期：2011.5

  A series of analogs of the amamistatin natural products was designed and synthesized to facilitate additional anticancer structure-activity relationships. The results indicate that the anticancer activity is relatively independent of stereochemistry, ester or amide linkage and replacement of the oxazoline/oxazole based iron-binding group with a catechol. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis and Stereochemical Assignment of Brasilibactin A
  作者：Judith M. Mitchell、Jared T. Shaw

  DOI：10.1021/ol070355o

  日期：2007.4.1

  Brasilibactin A, a naturally occurring siderophore related to the mycobactins, has been synthesized in six steps. Use of asymmetric titanium-mediated aldol reactions allowed the preparation of both diastereomers from a common synthetic intermediate, thus allowing the relative stereochemistry of the natural product to be assigned. Brasilibactin A exhibits no inhibition of histone deacetylases (HDACs) in spite of the N-formyl-N-hydroxy lysine moiety that is expected to affect the activity of these metal-dependent lysine-modifying enzymes.