(S)-4-hydroxymethyl-2-phenyl-oxazoline | 137649-96-8

• 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)-4-hydroxymethyl-2-phenyl-oxazoline
• 英文别名: (S)-(2-phenyl-4,5-dihydrooxazol-4-yl)methanol；[(4S)-2-phenyl-4,5-dihydro-1,3-oxazol-4-yl]methanol
• CAS: 137649-96-8
• 化学式: C₁₀H₁₁NO₂
• 分子量: 177.203
• InChiKey: NRVMSFKEGIGIHL-VIFPVBQESA-N

物化性质

• 熔点：
  100-101 °C
• 沸点：
  330.3±15.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-4-hydroxymethyl-2-phenyl-oxazoline 在 咪唑 、 盐酸 、 4-二甲氨基吡啶 、 正丁基锂 、 4 Angstroem MS 、 碘 、 sodium acetate 、 对甲苯磺酰肼 、 三苯基膦 作用下， 以 四氢呋喃 、 吡啶 、 正己烷 、 甲苯 为溶剂， 反应 37.5h， 生成 Acetic acid (R)-2-benzoylamino-4-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butyl ester
  参考文献：
  名称：

  Synthesis of β-d-Galactosyl Ceramide Methylene Isostere

  摘要：

  The methylene isostere of the glycosphingolipid beta-D-galactosyl N-palmitoyl C-18 ceramide has been synthesized by a linear reaction sequence starting from a beta-linked D-galactopyranosyl aldehyde. First, this sugar aldehyde was converted into a methylenephosphorane which in turn was coupled with N-Boc serinal acetonide. The double bond of the resulting olefin was reduced and the oxazolidine ring was cleaved and oxidized to give a C-glycosyl N-Boc alpha-amino butanal (three-carbon chain elongation). Then, an additional C-15 carbon chain was installed by addition of lithium 1-pentadecyne to the above glycosyl amino aldehyde. The syn/anti ratio (70:30) of the resulting mixture of amino alcohols was reversed (5:95) by an oxidation-reduction sequence to achieve the same stereochemistry as in the hydrophilic head of D-erythro-sphingosines. The major product was subjected to the reduction of the triple bond with LiAlH4 to give the olefin with E geometry. Finally the N-amide group was installed by reaction with palmitoyl chloride and the O-benzyl protective groups of the sugar moiety were removed by treatment with lithium in liquid NH3-THF. The final product was characterized as the O-acetyl derivative.

  DOI：

  10.1021/jo990398l
• 作为产物：
  描述：

  苯甲亚胺酸乙酯 在 二异丁基氢化铝 作用下， 以 甲醇 为溶剂， 生成 (S)-4-hydroxymethyl-2-phenyl-oxazoline
  参考文献：
  名称：

  Concise synthesis of (+)-serinolamide A

  摘要：

  Serinolamide A, isolated from a species of marine cyanobacteria, exhibits a moderate agonist effect and selectivity for the CB1 cannabinoid receptor, which is unusual for marine natural products. Herein, we reported a highly efficient enantiospecific first total synthesis of (+)-serinolamide A from L-serine in nine steps with 30% overall yield. The synthesis method provides a facile, practicable, and economical approach for the preparation of other similar endocanabinoid lipids. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.09.084

文献信息

• [EN] SUBSTITUTED PYRAZOLO[1,5-a]PYRIMIDINE COMPOUNDS AS mTOR INHIBITORS<br/>[FR] COMPOSÉS PYRAZOLO[1,5-A]PYRIMIDINE SUBSTITUÉS UTILISÉS COMME INHIBITEURS DE MTOR
  申请人：ARRAY BIOPHARMA INC

  公开号：WO2011029027A1

  公开（公告）日：2011-03-10

  Compounds of Formula I: and salts thereof in which R1, R2, R2a, R3, n, X and ring B have the meanings given in the specification, are inhibitors of mTOR and are useful in the treatment of diseases which are sensitive to inhibition of mTOR, such as cancers.

  公式I的化合物：以及其中R1、R2、R2a、R3、n、X和环B具有说明书中给出的含义的盐，是mTOR的抑制剂，可用于治疗对mTOR抑制敏感的疾病，如癌症。
• Synthesis of Optically Active Oxazoline Derivatives via Catalytic Asymmetric Desymmetrization of 1,3-Diols
  作者：Yutaro Tsuda、Masami Kuriyama、Osamu Onomura

  DOI：10.1002/chem.201103800

  日期：2012.2.27

  oxazolines: A synthetic method to prepare optically active oxazolines through a copper‐catalyzed asymmetric desymmetrization of 1,3‐diols has been successfully developed. This reaction system tolerated a diverse range of substrates to give the desired oxazoline derivatives in good to excellent yields with high enantioselectivities (see scheme).

  手性恶唑啉：已成功开发了一种通过铜催化的1,3-二醇不对称脱对称制备旋光恶唑啉的合成方法。该反应体系可耐受多种底物，从而以高至优异的收率和高对映选择性提供所需的恶唑啉衍生物（参见方案）。
• Asymmetric Addition to Chiral Aromatic and Unsaturated Oxazolines Using a Novel Chiral Auxiliary
  作者：A. I. Meyers、Wolfgang Schmidt、Marc J. Mckennon

  DOI：10.1055/s-1993-25842

  日期：——

  By utilizing S-serine, both enantiomers of the reduced methoxyamino alcohol (12) were efficiently prepared. The corresponding oxazolines, prepared from these auxiliaries, showed favorable properties toward additions to naphthalenes 22 and cyclohexene, 27.

  通过利用S-丝氨酸，成功合成了还原的甲氧基氨醇（12）的两种对映体。由这些辅助试剂制备的相应噁唑啉在与萘（22）和环己烯（27）的加成反应中显示出良好的性能。
• Synthesis and Antibacterial Activities of Yanglingmycin Analogues
  作者：Long-Bo Li、Wen-Jia Dan、Fang-Fang Tan、Li-Hui Cui、Zhi-Peng Yuan、Wen-Jun Wu、Ji-Wen Zhang

  DOI：10.1248/cpb.c14-00578

  日期：——

  The synthesis of Yanglingmycin and its enantiomer, along with eighteen Yanglingmycin analogues is reported. The structures were confirmed mainly by analyses of NMR spectral data. Antibacterial activity assays showed that Yanglingmycin and some of its analogues exhibited significant antibacterial activities against two important agricultural pathogenic bacteria, Ralstonia solanacearum and Pseudomonas syringae pv. actinidiae, with minimum inhibitory concentration (MIC) values ranging from 3.91 to 15.62 µg/mL. The antibacterial activities exhibited by Yanglingmycin and its analogues are promising, suggesting potential in the development of compounds for novel bactericides.

  报告了阳灵霉素及其对映体，以及十八种阳灵霉素类药物的合成。其结构主要通过核磁共振(NMR)光谱数据的分析得以确认。抗菌活性测定表明，阳灵霉素及其部分类药物对两种重要的农业病原菌——苏云金芽孢杆菌（Ralstonia solanacearum）和青枯病细菌（Pseudomonas syringae pv. actinidiae）具有显著的抗菌活性，最低抑菌浓度（MIC）值范围为3.91至15.62 µg/mL。阳灵霉素及其类药物表现出的抗菌活性具有潜力，建议在新型杀菌剂的化合物开发中具有应用前景。
• Incorporation and visualization of azido-functionalized N-oleoyl serinol in Jurkat cells, mouse brain astrocytes, 3T3 fibroblasts and human brain microvascular endothelial cells
  作者：T. Walter、L. Collenburg、L. Japtok、B. Kleuser、S. Schneider-Schaulies、N. Müller、J. Becam、A. Schubert-Unkmeir、J. N. Kong、E. Bieberich、J. Seibel

  DOI：10.1039/c6cc02879a

  日期：——

  Azido N-oleoyl serinol is a clickable ceramide analog for usage in a broad spectrum of cell lines like HBMEC.

  偶硝基N-油酰丝氨醇是一种可点击的鞘氨醇类似物，可用于广泛的细胞系，如HBMEC。