己基邻氨基苯甲酸酯 | 18189-05-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 己基邻氨基苯甲酸酯
• 英文名称: 2-amino-benzoic acid, hexyl ester
• 英文别名: n-Hexyl anthranilate；hexyl 2-aminobenzoate
• CAS: 18189-05-4
• 化学式: C₁₃H₁₉NO₂
• mdl: MFCD00459289
• 分子量: 221.299
• InChiKey: YMQOKTHPONOAKK-UHFFFAOYSA-N

物化性质

• LogP：
  4.726 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2922439000

反应信息

• 作为反应物：
  描述：

  己基邻氨基苯甲酸酯 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 生成 2-Hexyloxycarbonyl-benzenediazonium; chloride
  参考文献：
  名称：

  Steric Effects in Acid-Catalyzed Decomposition and Base-Catalyzed Cyclization of 1-(2-Alkoxycarbonylphenyl)-3-phenyltriazenes

  摘要：

  已合成了1-(2-烷氧羰基苯基)-3-苯基三氮烯的八种衍生物（R = 甲基、乙基、丙基、异丙基、丁基、异丁基、己基和烯丙基），并测量了它们的紫外-可见、红外、^1H和^13C核磁共振光谱。详细解释了核磁共振光谱。在25.0°C的52.1% w/w甲醇中测定了这些化合物的酸催化分解和碱催化环化的动力学。验证了单位反应阶数，并鉴定了环化产物。利用得到的pH-曲线计算了所有衍生物的酸催化分解催化速率常数kA和碱催化环化催化速率常数kB；这些常数已根据归纳和空间效应进行了解释。发现酸催化分解催化速率常数kA与取代基无关。碱催化环化催化速率常数kB在统计上显著取决于归纳和空间效应，对前者的敏感性更显著。实验结果及其解释证实了碱催化环化机制，形成四面体中间体作为速率限制步骤。

  DOI：

  10.1135/cccc19960751
• 作为产物：
  描述：

  正己醇 在 palladium on activated charcoal 硫酸 、 氢气 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 5.0h， 生成 己基邻氨基苯甲酸酯
  参考文献：
  名称：

  Oligoanthranilamides. Non-Peptide Subunits That Show Formation of Specific Secondary Structure

  摘要：

  A family of novel oligomers based on the anthranilamide nucleus has been prepared and shown to form well-defined secondary structural features. H-1 NMR and X-ray crystallographic techniques have demonstrated that intramolecular hydrogen bonds play a key role in stabilizing both linear sheet and helical conformational forms.

  DOI：

  10.1021/ja9539857

文献信息

• Novel Folding Patterns in a Family of Oligoanthranilamides:  Non-Peptide Oligomers That Form Extended Helical Secondary Structures
  作者：Yoshitomo Hamuro、Steven J. Geib、Andrew D. Hamilton

  DOI：10.1021/ja963449u

  日期：1997.11.1

  Anthranilamide derivatives are used as the basis for a series of novel oligomers that fold into helical secondary structures in the solid state. When combined with pyridine-2,6-dicarboxylic acid and 4,6-dimethoxy-1,3-diaminobenzene subunits, oligoanthranilamides can be induced to take up a coiled conformation corresponding to two turns of a helix. X-ray crystallography shows that intramolecular hydrogen

  邻氨基苯甲酰胺衍生物被用作一系列新型低聚物的基础，这些低聚物在固态下折叠成螺旋二级结构。当与吡啶-2,6-二羧酸和4,6-二甲氧基-1,3-二氨基苯亚基结合时，低聚邻氨基苯甲酰胺可以被诱导采取对应于两圈螺旋的卷曲构象。X 射线晶体学表明，分子内氢键和 π-π 堆积相互作用对于稳定扩展的螺旋结构很重要。此外，实验和计算 1H NMR 方法表明相关构象被氯仿溶液中的低聚物吸收。
• Structure-activity relationships of fungicidal N-benzoylanthranilic esters.
  作者：Osamu KIRINO、Shigeo YAMAMOTO、Toshiro KATO

  DOI：10.1271/bbb1961.44.2149

  日期：——

  The antifungal activity of 37 N-(methoxy-substituted benzoyl)anthranilic esters was tested on the powdery mildew of barley caused by Erysiphe graminis by the pot test. Among the methyl N-(methoxy-substituted benzoyl)anthranilates tested, 3, 4-dimethoxybenzoyl derivative exhibited the highest activity. The variation in fungicidal activity of N-(3, 4-dimethoxy-benzoyl)anthranilic esters was shown to be related with variation in hydrophobicity and the electronic property of the alcohol moiety of the ester. The branching at the α-position of the alcohol moiety of the ester was detrimental to the activity.

  37种N-(甲氧基取代的苯甲酰)蒽醌酯的抗真菌活性通过盆栽试验在由小麦白粉病（Erysiphe graminis）引起的大麦粉状霉菌上进行了测试。在测试的甲基N-(甲氧基取代的苯甲酰)蒽醌酯中，3,4-二甲氧基苯甲酰衍生物表现出最高的活性。N-(3,4-二甲氧基苯甲酰)蒽醌酯的杀真菌活性的变化被证明与酯的醇基的疏水性和电子性质的变化相关。醇基在α位的支链对活性是有害的。
• Plasticized thermoset resin, and associated cured resin, method of curing, and article comprising cured resin
  申请人：The University of Massachusetts

  公开号：US10913844B2

  公开（公告）日：2021-02-09

  A curable composition includes a hydrogen-bonded prepolymer, a plasticizer, and, optionally, a crosslinking agent. The plasticizer includes a reactive plasticizer having structure (I), (II), or (III), wherein X is —OR1, —N(R1)2, —R4—OR1, or —R4—N(R1)2, wherein R1 is independently at each occurrence hydrogen or C1-6 alkyl, and R4 is C1-12 alkylene; y is zero or 1; z is zero or 1; R2 is C1-12 alkyl; and R3 is C1-12 alkyl when z is 1, or R3 is C1-12 alkyl or H when z is zero.

  一种可固化组合物包括氢键预聚物、增塑剂和可选的交联剂。增塑剂包括具有结构(I)、(II)或(III)的反应性增塑剂，其中 X 为-OR1、-N(R1)2、-R4-OR1 或-R4-N(R1)2，其中 R1 在每次出现时独立地为氢或 C1-6 烷基，R4 为 C1-12 亚烷基；y 为零或 1；z 为零或 1；R2 为 C1-12 烷基；当 z 为 1 时，R3 为 C1-12 烷基，或当 z 为零时，R3 为 C1-12 烷基或 H。
• Photobleaching Activity of 2-(Phenylamino)methylidenecyclohexane-1,3-diones in Tobacco (<i>Nicotiana</i> <i>tabacum</i>) Cultured Cells
  作者：Jing-Ming Wang、Tadao Asami、Fan-Sik Che、Noboru Murofushi、Shigeo Yoshida

  DOI：10.1021/jf960962i

  日期：1997.7.1

  A series of phenylalkylidenecyclohexane-1,3-dione derivatives were designed and synthesized as vinylogous analogs of phthalimides, which are known photobleaching herbicides. The bleaching activity of synthesized compounds was assayed with photomixotrophic tobacco cultured cells under either light or dark conditions. Both the chlorophyll and the carotenoid contents of the cells treated with the cyclic diones decreased to almost zero within 24 h under the light condition but not under the dark condition. This rapid emergence of bleaching activity with light is one of the most distinctive actions of Protox-inhibiting herbicides; however, the cyclic dione did not inhibit protoporphyrinogen oxidase in vitro. Thus, we concluded that the cyclic diones possessed a different herbicidal mode of action from Protox-inhibiting herbicide.
• Synthesis, antimicrobial evaluation, ot-QSAR and mt-QSAR studies of 2-amino benzoic acid derivatives
  作者：Kuldeep Mahiwal、Pradeep Kumar、Balasubramanian Narasimhan

  DOI：10.1007/s00044-010-9537-5

  日期：2012.3

  A series of 2-amino benzoic acid derivatives (1-28) were synthesized and evaluated for their in vitro antimicrobial activity against the panel of Gram positive, Gram negative bacterial and fungal strains. The results of antimicrobial studies indicated that, in general, the synthesized compounds were found to be bacteriostatic and fungistatic in action. QSAR studies performed by the development of one target and multi target models indicated that multi-target model was effective in describing the antimicrobial activity as well demonstrated the effect of structural parameters viz. LUMO, (3)chi(v) and W on antimicrobial activity of 2-amino benzoic acid derivatives.