aerugine | 118491-87-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: aerugine
• 英文别名: 2-[4-(Hydroxymethyl)-4,5-dihydro-1,3-thiazol-2-yl]phenol；2-[4-(hydroxymethyl)-4,5-dihydro-1,3-thiazol-2-yl]phenol
• CAS: 118491-87-5
• 化学式: C₁₀H₁₁NO₂S
• 分子量: 209.269
• InChiKey: CQCVSXXDUMTFCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 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：
  78.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  aerugine 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 生成 2-(2-Hydroxyphenyl)thiazole-4-carboxaldehyde
  参考文献：
  名称：

  Stereochemical Assignment of the Pyochelins

  摘要：

  The synthesis of pyochelin has been much improved but gives four stereoisomers. The stereochemistry of the two naturally occurring pyochelins I and II has been assigned, based on (1) the similarity of the NMR spectra of pyochelin I methyl ester to those for 4-methylpyochelin I methyl ester, whose X-ray structure has been determined and relative stereochemistry assigned; (2) comparison of the rotation of the natural material to that of pyochelin I methyl ester synthesized from N-methyl-L-cysteine methyl ester, which is not expected to epimerize during the synthesis and thus assigns pyochelin I methyl ester as 4'R,2 '' R,4 '' R; and (3) the known facile epimerization at C-2 '' of 2 ''-substituted thiazolidine-4-carboxylic acids, which assigns the other (unfavored) naturally occurring isomer, pyochelin II, as 4'R,2 '' S,4 '' R. The remaining two synthetic products, neopyochelin I methyl ester and neopyochelin II methyl ester, were assigned the stereochemistry 4'S,2 '' S,4 '' R and 4'S,2 '' R,4 '' R, respectively, based on (1) the use of N-methyl-L-cysteine methyl ester in their synthesis, which establishes C-4 '' as R; (2) the known instability at C-2 '', which favors neopyochelin II (2 '' R) over neopyochelin I (2 '' S); and (3) the requirement of nonidentity with pyochelins I and II, which requires the S configuration at C-4'.

  DOI：

  10.1021/jo00114a029
• 作为产物：
  描述：

  邻羟基苯甲腈 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 aq. phosphate buffer 、 乙醚 、 二氯甲烷 为溶剂， 反应 25.17h， 生成 aerugine
  参考文献：
  名称：

  聚合的古铁青霉素为Ga 3+配合物的全合成

  摘要：

  含铁细胞piscibactin是参与致病细菌的铁摄取的主要毒力因子发光菌damselae亚种。piscicida和Anguillarum弧菌分别负责鱼类细菌光致细菌（巴氏杆菌病）和弧菌病。描述了使用l- / d-半胱氨酸作为手性试剂和梅德鲁姆酸的Ga 3+络合物的收敛全合成。酸敏感的β-羟基-2,4-二取代的噻唑啉部分和方便的保护基团的合成中的Staudinger还原/ Aza-Wittig工艺是该合成的关键步骤。

  DOI：

  10.1021/acs.orglett.0c03850

文献信息

• Thiazoline‐Iridium (III) Complexes and Immobilized Nanomaterials as Selective Catalysts in <i>N</i> ‐Alkylation of Amines with Alcohols
  作者：Serpil Denizaltı、Serkan Dayan、Salih Günnaz、Ertan Şahin

  DOI：10.1002/aoc.5970

  日期：2020.12

  thiazoline‐iridium (III) complexes (4–7) derived from cysteine were prepared and fully characterized by conventional methods. The molecular structure of complex 5 was also determined by single‐crystal X‐ray diffraction. These complexes were evaluated as catalysts for hydrogen‐borrowing reactions of amines with alcohols. In particular, complex 5 showed the best activity as catalyst. Various amines have

  在这项研究中，一个新的系列噻唑啉的铱（III）配合物（4 - 7）来自半胱氨酸制备并通过常规方法充分表征。配合物5的分子结构也通过单晶X射线衍射确定。这些络合物被评估为胺与醇的氢借位反应的催化剂。特别地，配合物5显示出作为催化剂的最佳活性。各种胺已被醇烷基化，可提供中等至良好的收率（33–99％）。此外，采用最佳催化剂5进行超声处理，制备了固定化的纳米材料（M 1,2）。分别使用多壁碳纳米管（MWCNT）和氧化石墨烯（GO），并通过X射线衍射（XRD），傅里叶变换红外（FT-IR）光谱，场发射扫描电子显微镜（FE-SEM）进行表征，能量色散X射线（EDX）光谱和电感耦合等离子体质谱（ICP-MS）。的中号1,2纳米材料也进行了测试，如用于模型催化反应的催化剂Ñ烷基化。的中号1的纳米材料显示出比显著更高的活性中号2纳米材料。的中号1催化剂通过过滤回收并用于与高转化率4个催化循环（99％，97％，96％，和86％）再利用。
• METHODS AND COMPOSITIONS RELATED TO NEUROACTIVE THIAZOLINE COMPOUNDS
  申请人：Schmidt Eric W.

  公开号：US20140018400A1

  公开（公告）日：2014-01-16

  In one aspect, the invention relates to compounds having a general structure: and methods of using same to modulate calcium release. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

  在某个方面，本发明涉及具有一般结构的化合物：以及使用同样的方法来调节钙释放。本摘要旨在作为扫描工具，用于在特定技术领域进行搜索，不旨在限制本发明。
• Structure of aerugine from Pseudomonas aeruginosa
  作者：A. Zunnundzhanov、I. A. Bessonova、N. D. Abdullaev、D. K. Ogai

  DOI：10.1007/bf00597805

  日期：1987.7
• Identification of the bacterial metabolite aerugine as potential trigger of human dopaminergic neurodegeneration
  作者：Anna-Katharina Ückert、Sina Rütschlin、Simon Gutbier、Nathalie Christine Wörz、Mahfuzur R. Miah、Airton C. Martins、Isa Hauer、Anna-Katharina Holzer、Birthe Meyburg、Ann-Kathrin Mix、Christof Hauck、Michael Aschner、Thomas Böttcher、Marcel Leist

  DOI：10.1016/j.envint.2023.108229

  日期：2023.10
• US9751847B2
  申请人：——

  公开号：US9751847B2

  公开（公告）日：2017-09-05