tert-butyl 3-chloro-4-hydroxybenzoate | 258330-98-2

• 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: tert-butyl 3-chloro-4-hydroxybenzoate
• CAS: 258330-98-2
• 化学式: C₁₁H₁₃ClO₃
• 分子量: 228.675
• InChiKey: WYEFGGSDSSINRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-chloro-4-hydroxybenzoate 在 potassium tert-butylate 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 tris(4-carboxyl-2-chlorophenyl) trimesate
  参考文献：
  名称：

  Mechanism of Site-Directed Protein Cross-Linking. Protein-Directed Selectivity in Reactions of Hemoglobin with Aryl Trimesates

  摘要：

  Site-directed cross-linking of hemoglobin has become an efficient way to produce a structurally defined altered protein with desirable functional properties. The reagent trimesoyl tris(3,5-dibromosalicylate) (1) introduces a bis amide cross-link derived from the epsilon-amino groups of the side chains of the two beta-Lys-82 residues in human hemoglobin. The basis of its specificity was investigated using a set of analogues of 1 (2-12). There are marked differences in the reaction patterns of these compounds with amino groups in hemoglobin compared to reactions with n-propylamine. The compounds that effectively modify the protein contain a carboxyl group ortho to the phenolic oxygen of the ester, while materials with meta or para carboxyl groups give little or no reaction. In contrast, the reactions with n-propylamine are slowest with the ortho carboxyl materials. Addition of the unreactive compound 5 to a solution containing hemoglobin reduces the ability of 1 to modify the protein, showing that the unreactive compound binds but does not react. On the basis of these observations and the known reaction patterns of salicylates, it is clear that: the environment in the protein controls the reaction, regardless of the inherent reactivity of the reagent. We propose that the carboxyl group positions the reagent critically within the protein. Only the ortho arrangement permits transfer of the acyl function to the nucleophile.

  DOI：

  10.1021/jo991514n
• 作为产物：
  描述：

  3-氯-4-羟基苯甲酸 、 叔丁醇 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以71%的产率得到tert-butyl 3-chloro-4-hydroxybenzoate
  参考文献：
  名称：

  用于木材共价修饰的新型烟碱结构：一种环保的防虫方法

  摘要：

  木材在室外条件下经常受到环境影响，这限制了其使用寿命和可用性。为了抵消昆虫造成的破坏过程，我们开发了一种新颖且更环保的方法，通过有机杀虫剂进行共价改性来保护木质材料。从天然杀虫剂尼古丁衍生的一类重要的合成杀虫剂开始，吡虫啉的各种新型羧酸衍生物被开发出来。这些活化的新烟碱类杀虫剂用于木材羟基的化学改性。与传统的木材防腐方法相比，杀菌剂仅在有限的时间内物理结合到表面，防腐剂的共价固定保证了对木材害虫的永久效果，这在标准化生物测试中得到了证明。此外，由未结合的新烟碱类杀虫剂引起的环境相互作用显着减少，因为既需要较小的施用量，又防止了活性成分的浸出。通过最大限度地减少害虫侵扰，可以延长材料的使用寿命，同时保留材料的自然外观。

  DOI：

  10.1039/d0ra02071k

文献信息

• Barluenga, Jose; Jimenez-Aquino, Agustin; Aznar, Fernando, Journal of the American Chemical Society, 2009, vol. 131, p. 4031 - 4041
  作者：Barluenga, Jose、Jimenez-Aquino, Agustin、Aznar, Fernando、Valdes, Carlos

  DOI：——

  日期：——
• Novel nicotinoid structures for covalent modification of wood: an environmentally friendly way for its protection against insects
  作者：Martin Söftje、Sophie Acker、Rudy Plarre、Jan C. Namyslo、Dieter E. Kaufmann

  DOI：10.1039/d0ra02071k

  日期：——

  Timber is constantly exposed to environmental influences under outdoor conditions which limits its lifetime and usability. In order to counteract the damaging processes caused by insects, we have developed a novel and more environmentally friendly method to protect wood materials via covalent modification by organic insecticides. Starting with an important class of synthetic insecticides which are

  木材在室外条件下经常受到环境影响，这限制了其使用寿命和可用性。为了抵消昆虫造成的破坏过程，我们开发了一种新颖且更环保的方法，通过有机杀虫剂进行共价改性来保护木质材料。从天然杀虫剂尼古丁衍生的一类重要的合成杀虫剂开始，吡虫啉的各种新型羧酸衍生物被开发出来。这些活化的新烟碱类杀虫剂用于木材羟基的化学改性。与传统的木材防腐方法相比，杀菌剂仅在有限的时间内物理结合到表面，防腐剂的共价固定保证了对木材害虫的永久效果，这在标准化生物测试中得到了证明。此外，由未结合的新烟碱类杀虫剂引起的环境相互作用显着减少，因为既需要较小的施用量，又防止了活性成分的浸出。通过最大限度地减少害虫侵扰，可以延长材料的使用寿命，同时保留材料的自然外观。
• Mechanism of Site-Directed Protein Cross-Linking. Protein-Directed Selectivity in Reactions of Hemoglobin with Aryl Trimesates
  作者：Ronald Kluger、Vittorio De Stefano

  DOI：10.1021/jo991514n

  日期：2000.1.1

  Site-directed cross-linking of hemoglobin has become an efficient way to produce a structurally defined altered protein with desirable functional properties. The reagent trimesoyl tris(3,5-dibromosalicylate) (1) introduces a bis amide cross-link derived from the epsilon-amino groups of the side chains of the two beta-Lys-82 residues in human hemoglobin. The basis of its specificity was investigated using a set of analogues of 1 (2-12). There are marked differences in the reaction patterns of these compounds with amino groups in hemoglobin compared to reactions with n-propylamine. The compounds that effectively modify the protein contain a carboxyl group ortho to the phenolic oxygen of the ester, while materials with meta or para carboxyl groups give little or no reaction. In contrast, the reactions with n-propylamine are slowest with the ortho carboxyl materials. Addition of the unreactive compound 5 to a solution containing hemoglobin reduces the ability of 1 to modify the protein, showing that the unreactive compound binds but does not react. On the basis of these observations and the known reaction patterns of salicylates, it is clear that: the environment in the protein controls the reaction, regardless of the inherent reactivity of the reagent. We propose that the carboxyl group positions the reagent critically within the protein. Only the ortho arrangement permits transfer of the acyl function to the nucleophile.