methyl 5-hydroxy-4-benzoxazolecarboxylate | 155012-53-6

• 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: methyl 5-hydroxy-4-benzoxazolecarboxylate
• 英文别名: methyl 5-hydroxybenzoxazol-4-carboxylate；methyl 5-hydroxy-1,3-benzoxazole-4-carboxylate
• CAS: 155012-53-6
• 化学式: C₉H₇NO₄
• 分子量: 193.159
• InChiKey: JGUITQWNVXOFLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  72.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 5-hydroxy-4-benzoxazolecarboxylate 在 palladium 10% on activated carbon 、 氢气 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 lithium iodide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙腈 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 70.0h， 生成 heterobactin A
  参考文献：
  名称：

  Synthesis of heterobactins A and B and Nocardia heterobactin

  摘要：

  The synthesis of the Rhodococcus erythropolis siderophores heterobactins A and B, and the structurally related Nocardia heterobactin, is described. Two approaches for the assembly of these asymmetric ligand donor chelators are explored. In the first approach, a scheme predicated on the biosynthesis of the Para coccus denitrificans siderophore, parabactin, is employed. In this approach, the central donor synthon is added last. In the second scheme, the central donor and the terminal 2,3-dihydroxybenzoyl fragment are first fixed to the ligand's D-ornithine backbone. This is followed by condensation with the cyclic ornithine hydroxamate glycine segment. The schemes offer a flexible approach to other heterobactins. Job's plots suggest that heterobactin A and Nocardia heterobactin form 1:1 ligand/metal complexes, while heterobactin B forms a 3:2 ligand/metal complex. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.003
• 作为产物：
  描述：

  methyl 2-amino-3,6-dihydroxybenzoate hydrochloride 、 原甲酸三乙酯 以 乙醇 为溶剂， 反应 24.0h， 以75%的产率得到methyl 5-hydroxy-4-benzoxazolecarboxylate
  参考文献：
  名称：

  Synthesis of heterobactins A and B and Nocardia heterobactin

  摘要：

  The synthesis of the Rhodococcus erythropolis siderophores heterobactins A and B, and the structurally related Nocardia heterobactin, is described. Two approaches for the assembly of these asymmetric ligand donor chelators are explored. In the first approach, a scheme predicated on the biosynthesis of the Para coccus denitrificans siderophore, parabactin, is employed. In this approach, the central donor synthon is added last. In the second scheme, the central donor and the terminal 2,3-dihydroxybenzoyl fragment are first fixed to the ligand's D-ornithine backbone. This is followed by condensation with the cyclic ornithine hydroxamate glycine segment. The schemes offer a flexible approach to other heterobactins. Job's plots suggest that heterobactin A and Nocardia heterobactin form 1:1 ligand/metal complexes, while heterobactin B forms a 3:2 ligand/metal complex. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.003

文献信息

• Condensed heterocyclic derivatives and herbicides
  申请人：Kumiai Chemical Industry Co., Ltd.

  公开号：US05616537A1

  公开（公告）日：1997-04-01

  A condensed heterocyclic derivative of the formula (I): ##STR1## (wherein R is a hydroxyl group, R.sup.3 or R.sup.4 is an alkoxy group, W is an oxygen atom, Yn is a hydrogen atom, Z is a methine group, and A is a 5- or 6-membered heterocyclic ring which may be substituted, and a herbicide, are presented. When used for paddy field treatment, upland soil treatment and foliage treatment, the condensed heterocyclic derivative of the present invention exhibits excellent herbicidal activities against gramineous and non-gramineous weeds without adversely affecting crop plants.

  一种式(I)的缩合杂环衍生物：##STR1##（其中R为羟基，R.sup.3或R.sup.4为烷氧基，W为氧原子，Yn为氢原子，Z为甲川基，A为可被取代的5或6元杂环环），以及一种除草剂，被提出。当用于水稻田处理、旱地土壤处理和叶面处理时，本发明的缩合杂环衍生物对禾本科和非禾本科杂草表现出优异的除草活性，而对作物植物无不良影响。
• CONDENSED HETEROCYCLIC DERIVATIVE AND WEEDKILLER
  申请人：KUMIAI CHEMICAL INDUSTRY CO., LTD.

  公开号：EP0606489A1

  公开（公告）日：1994-07-20

  A condensed heterocyclic derivative represented by general formula (I) and a weedkiller, wherein R represents hydroxy, R³ and R⁴ represent each alkoxy, W represents oxygen, Yn represents hydrogen, Z represents methine, and A represents a 5- or 6-membered heterocyclic group which may be substituted. The derivative does not injure crops in the water treatment in a paddy field, upland farming, soil treatment and foliage treatment, and has an excellent weedkilling activity against gramineous and nongramineous weeds.

  一种由通式（I）代表的缩合杂环衍生物和一种除草剂，其中 R 代表羟基，R³ 和 R⁴ 分别代表烷氧基，W 代表氧，Yn 代表氢，Z 代表甲烷，A 代表可被取代的 5 或 6 元杂环基团。该衍生物在水田水处理、高地耕作、土壤处理和叶面处理中不会伤害作物，对禾本科杂草和非禾本科杂草具有优异的除草活性。
• US5616537A
  申请人：——

  公开号：US5616537A

  公开（公告）日：1997-04-01
• US5770544A
  申请人：——

  公开号：US5770544A

  公开（公告）日：1998-06-23
• Synthesis of heterobactins A and B and Nocardia heterobactin
  作者：Raymond J. Bergeron、Shailendra Singh、Neelam Bharti

  DOI：10.1016/j.tet.2011.03.003

  日期：2011.5

  The synthesis of the Rhodococcus erythropolis siderophores heterobactins A and B, and the structurally related Nocardia heterobactin, is described. Two approaches for the assembly of these asymmetric ligand donor chelators are explored. In the first approach, a scheme predicated on the biosynthesis of the Para coccus denitrificans siderophore, parabactin, is employed. In this approach, the central donor synthon is added last. In the second scheme, the central donor and the terminal 2,3-dihydroxybenzoyl fragment are first fixed to the ligand's D-ornithine backbone. This is followed by condensation with the cyclic ornithine hydroxamate glycine segment. The schemes offer a flexible approach to other heterobactins. Job's plots suggest that heterobactin A and Nocardia heterobactin form 1:1 ligand/metal complexes, while heterobactin B forms a 3:2 ligand/metal complex. (C) 2011 Elsevier Ltd. All rights reserved.