5,7-di-tert-butyl-3-(4-hydroxyphenyl)benzofuran-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 5,7-di-tert-butyl-3-(4-hydroxyphenyl)benzofuran-2-one
• 英文别名: 5,7-di-tert-butyl-3-(4-hydroxyphenyl)benzofuran-2(3H)-one；5,7-ditert-butyl-3-(4-hydroxyphenyl)-3H-1-benzofuran-2-one
• 化学式: C₂₂H₂₆O₃
• 分子量: 338.447
• InChiKey: OOKTZSOAVMJNDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 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：

  5,7-di-tert-butyl-3-(4-hydroxyphenyl)benzofuran-2-one 在 sodium hydroxide 、 potassium hexacyanoferrate(III) 作用下， 以 甲醇 、 水 为溶剂， 反应 0.5h， 以40%的产率得到5,7-Ditert-butyl-3-[5,7-ditert-butyl-3-(4-hydroxyphenyl)-2-oxo-1-benzofuran-3-yl]-3-(4-hydroxyphenyl)-1-benzofuran-2-one
  参考文献：
  名称：

  通过静电相互作用增强机械载体活化

  摘要：

  机械载体响应机械刺激而改变其化学结构，被广泛用于开发机械响应材料，其反应性受周围环境的影响很大。在这里，我们专注于静电相互作用对机械载体活化的影响。制备了一系列具有离子官能团的自由基型机械载体，以及这些带有二羧酸基团和二价离子的自由基型机械载体的混合体系，并通过球磨和随后的电子实验研究了它们在本体中的机械响应性顺磁共振波谱测量。结果表明，机械响应性受将静电相互作用引入机械载体的控制。

  DOI：

  10.1246/bcsj.20220021
• 作为产物：
  描述：

  2,4-二叔丁基苯酚 、 4-羟基扁桃酸 在 甲烷磺酸 、 溶剂黄146 作用下， 反应 3.0h， 以56%的产率得到5,7-di-tert-butyl-3-(4-hydroxyphenyl)benzofuran-2-one
  参考文献：
  名称：

  材料特性对涂料应用中机械活性动态网络聚合物的损伤报告和自修复性能的影响

  摘要：

  我们对动态聚合物网络涂层的材料性能对其自愈和损伤报告性能的影响进行了详细研究。合成了一系列含有损伤报告二芳基联苯并呋喃酮单元的可逆聚丙烯酸酯聚氨酯网络，并通过纳米压痕和差示扫描量热实验测量了它们的材料性能（例如压痕模量、硬度模量和玻璃化转变温度）。动态聚合物网络涂层的损伤报告和自修复性能与聚合物网络涂层的材料性能表现出相反的趋势。具有低玻璃化转变温度 (~10 °C) 和压痕硬度 (20 MPa) 的软聚合物网络涂层表现出更好的自修复性能（几乎 100%），但损伤报告性能比具有高玻璃化温度的硬聚合物网络涂层差两倍-转变温度（35~50℃）和压痕硬度（150~200MPa）。动态聚合物网络涂层的这些特点是独一无二的；它们在弹性体、薄膜和水凝胶中没有观察到，聚合物网络通过这些方式与基材表面结合。有证据表明，控制聚合物的物理性能是设计基于力基团的高性能自修复和损伤报告聚合物涂层的关键因素。

  DOI：

  10.3390/molecules26092468

文献信息

• 3-(2-acyloxyethoxyphenyl)benzofuran-2-ones for use as stabilizers
  申请人：Ciba-Geigy Corporation

  公开号：US05428162A1

  公开（公告）日：1995-06-27

  Novel compounds of the formula (1), ##STR1## in which R.sub.1 is hydrogen or acyl, R.sub.2 to R.sub.5 are independently hydrogen, chloro, alkyl phenylalkyl, aryl, cycloalkyl, alkoxy, alkylthio, hydroxy, amino or substituted amino, R.sub.6 is hydrogen, R.sub.7 to R.sub.10 are independently hydrogen, alkyl or alkoxy, R.sub.17 or R.sub.19 is hydrogen or alkyl, and R.sub.18 is hydrogen, alkyl, aralkyl or aryl, are described for use as stabilizers for organic materials against thermal, oxidative or light-induced degradation.

  化合物的新颖化合物的公式（1），##STR1##其中R.sub.1是氢或酰基，R.sub.2到R.sub.5分别是氢，氯，烷基苯基烷基，芳基，环烷基，烷氧基，烷基硫基，羟基，氨基或取代氨基，R.sub.6是氢，R.sub.7到R.sub.10分别是氢，烷基或烷氧基，R.sub.17或R.sub.19是氢或烷基，R.sub.18是氢，烷基，芳基烷基或芳基，用作有机材料的稳定剂，抵抗热、氧化或光诱导降解。
• [EN] PHENOLIC METAL SALTS AND THEIR PHENOLIC ACIDS AS POLYMER STABILIZERS<br/>[FR] SELS MÉTALLIQUES PHÉNOLIQUES ET LEURS ACIDES PHÉNOLIQUES UTILISÉS COMME STABILISANTS DE POLYMÈRES
  申请人：BASF SE

  公开号：WO2019008002A1

  公开（公告）日：2019-01-10

  The invention relates to a composition comprising a) a polymer and b) (i) a phenolic metal salt of formula (I) Mn+ (L-)n wherein n is 1, 2 or 3, Mn+ is a metal ion and L- is an anion of formula (II) wherein A1 and A2 are both -CH2-CH2-, -CH=CH- or -CH2- or A1 is -CH=CH- and A2 is -CH2- or A1 is -CH2-CH2- and A2 is -CH2-, R1, R2, R4 and R5 are independently from each other C1-C4 alkyl, R3 is H or C1-C4 alkyl, or (ii) a bisphenolic compound of formula (III) wherein A1, A2, and R1 to R5 are as mentioned above, wherein the amount of component b) is from 0.0005 to 0.9 % by weight based on the weight of component a). The phenolic metal salt of formula (I) or the bisphenolic compound of formula (III) stabilizes the polymer against oxidative, thermal or light-induced degradation. Further embodiments are also an additive mixture comprising the phenolic metal salt of formula (I) or the bisphenolic compound of formula (III) and a further additive or a process for adding the component b) to the polymer, for example in an extruder.

  本发明涉及一种组合物，包括a）聚合物和b）（i）式（I）的酚类金属盐Mn+（L）n，其中n为1、2或3，Mn+为金属离子，L-为式（II）的阴离子，其中A1和A2均为-CH2-CH2-，-CH=CH-或-CH2-，或者A1为-CH=CH-，A2为-CH2-或A1为-CH2-CH2-，A2为-CH2-，R1、R2、R4和R5各自独立地为C1-C4烷基，R3为H或C1-C4烷基；或（ii）式（III）的双酚类化合物，其中A1、A2和R1至R5如上所述，其中组分b）的量为组分a）的重量的0.0005至0.9％。式（I）的酚类金属盐或式（III）的双酚类化合物可以使聚合物对氧化、热或光诱导降解具有稳定作用。进一步的实施方式还包括包括式（I）的酚类金属盐或式（III）的双酚类化合物和其他添加剂的混合物，或将组分b）添加到聚合物中的方法，例如在挤出机中。
• 3-PHENYL-3H-1-BENZOFURAN-2-ONE COMPOUNDS AND COMPOSITIONS COMPRISING THE SAME
  申请人：Milliken & Company

  公开号：US20190225780A1

  公开（公告）日：2019-07-25

  A 3-phenyl-3H-1-benzofuran-2-one compound is substituted with one or more acyloxy groups comprising 26 or more carbon atoms. A compound comprises two or more 3-phenyl-3H-1-benzofuran-2-one moieties and a second moiety selected from the group consisting of divalent and polyvalent C 4 -C 60 hydrocarbon moieties. Each 3-phenyl-3H-1-benzofuran-2-one moiety is covalently bound to an open valence of the second moiety through a linking group selected from the group consisting of a carboxy group and oxyalkylene ester moieties. A composition comprises the 3-phenyl-3H-1-benzofuran-2-one compound described above or the compound described above comprising two or more 3-phenyl-3H-1-benzofuran-2-one moieties.

  一种3-苯基-3H-1-苯并呋喃-2-酮化合物被一个或多个含有26个或更多碳原子的酰氧基取代。一种化合物包括两个或更多3-苯基-3H-1-苯并呋喃-2-酮基团和从双价和多价C4-C60碳氢化合物基团组成的第二个基团。每个3-苯基-3H-1-苯并呋喃-2-酮基团通过从羧基和氧烷基酯基团组成的连接基团共价结合到第二个基团的开放价。一种组合物包括上述3-苯基-3H-1-苯并呋喃-2-酮化合物或包括两个或更多3-苯基-3H-1-苯并呋喃-2-酮基团的化合物。
• 3-(acyloxyphenyl)benzofuran-2-one stabilisers
  申请人：Ciba-Geigy Corporation

  公开号：US05488117A1

  公开（公告）日：1996-01-30

  Compounds of the formula (1) ##STR1## in which R.sub.2, R.sub.3, R.sub.4 and R.sub.5 independently of one another, are hydrogen, C.sub.1 -C.sub.25 alkyl, C.sub.7 -C.sub.9 phenylalkyl, unsubstituted or C.sub.1 -C.sub.4 alkyl-substituted phenyl, unsubstituted or C.sub.1 -C.sub.4 alkyl-substituted C.sub.5 -C.sub.8 cycloalkyl; C.sub.1 -C.sub.18 alkoxy, hydroxyl, C.sub.1 -C.sub.25 alkanoyloxy, C.sub.3 -C.sub.25 alkenoyloxy, C.sub.3 -C.sub.25 alkanoyloxy which is interrupted by oxygen, sulfur or >N--R.sub.16 ; C.sub.6 -C.sub.9 cycloalkylcarbonyloxy, benzoyloxy or C.sub.1 -C.sub.12 alkyl-substituted benzoyloxy, where R.sub.16 is hydrogen or C.sub.1 -C.sub.8 alkyl, or, furthermore, the radicals R.sub.2 and R.sub.3 or the radicals R.sub.4 and R.sub.5 together with the carbon atoms to which they are bound form a phenyl ring, R.sub.4 is additionally --(CH.sub.2).sub.n --COR.sub.11, in which n is 0, 1 or 2, R.sub.11 is hydroxyl, ##STR2## R.sub.14 and R.sub.15, independently of one another, are hydrogen or C.sub.1 -C.sub.18 alkyl, M is an r-valent metal cation and r is 1, 2 or 3, R.sub.7, R.sub.8, R.sub.9 and R.sub.10, independently of one another, are hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, with the proviso that at least one of the radicals R.sub.7, R.sub.8, R.sub.9 and R.sub.10 is hydrogen and, in the case where R.sub.3, R.sub.5, R.sub.6, R.sub.7 and R.sub.10 are hydrogen, R.sub.4 is additionally a radical of the formula (2) ##STR3## in which R.sub.2, R.sub.8 and R.sub.9 are as defined above and R.sub.1 is as defined below for m=1, and R.sub.12 and R.sub.13, independently of one another, are hydrogen, C.sub.1 -C.sub.12 alkyl or phenyl, m is 1 or 2, and, in the case where m is 1, R.sub.1 is hydrogen, C.sub.1 -C.sub.25 alkanoyl, C.sub.3 -C.sub.25 alkenoyl, C.sub.3 -C.sub.25 alkanoyl which is interrupted by oxygen, sulfur or >N--R.sub.16 ; C.sub.6 -C.sub.9 cycloalkylcarbonyl, benzoyl or C.sub.1 -C.sub.12 alkyl-substituted benzoyl, R.sub.16 is as defined above and R.sub.6 is hydrogen or a radical of the formula (3) ##STR4## in which R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.7, R.sub.8, R.sub.9 and R.sub.10 are as defined above, and, in the case where m is 2, R.sub.1 is ##STR5## in which R.sub.17 is a direct bond, C.sub.1 -C.sub.18 alkylene, C.sub.2 -C.sub.18 alkylene which is interrupted by oxygen, sulfur or >N--R.sub.16 ; C.sub.2 -C.sub.18 alkenylene, C.sub.2 -C.sub.20 alkylidene, C.sub.7 -C.sub.20 phenylalkylidene, C.sub.5 -C.sub.8 cycloalkylene, C.sub.7 -C.sub.8 bicycloalkylene or phenylene, R.sub.16 is as defined above and R.sub.6 is hydrogen, are described as stabilizers for organic materials against oxidative, thermal or light-induced degradation.

  公式（1）的化合物 ##STR1## 其中R.sub.2，R.sub.3，R.sub.4和R.sub.5独立地为氢，C.sub.1-C.sub.25烷基，C.sub.7-C.sub.9苯基烷基，未取代或C.sub.1-C.sub.4烷基取代的苯基，未取代或C.sub.1-C.sub.4烷基取代的C.sub.5-C.sub.8环烷基；C.sub.1-C.sub.18烷氧基，羟基，C.sub.1-C.sub.25脂肪酰氧基，C.sub.3-C.sub.25烯酰氧基，被氧，硫或>N--R.sub.16打断的C.sub.3-C.sub.25脂肪酰氧基；C.sub.6-C.sub.9环烷基羰氧基，苯甲酰氧基或C.sub.1-C.sub.12烷基取代的苯甲酰氧基，其中R.sub.16为氢或C.sub.1-C.sub.8烷基，或者，进一步，基团R.sub.2和R.sub.3或基团R.sub.4和R.sub.5与它们结合的碳原子一起形成苯环，R.sub.4另外为--(CH.sub.2).sub.n --COR.sub.11，其中n为0，1或2，R.sub.11为羟基，##STR2##R.sub.14和R.sub.15独立地为氢或C.sub.1-C.sub.18烷基，M为r价金属阳离子，r为1，2或3，R.sub.7，R.sub.8，R.sub.9和R.sub.10独立地为氢，C.sub.1-C.sub.4烷基或C.sub.1-C.sub.4烷氧基，但至少有一个基团R.sub.7，R.sub.8，R.sub.9和R.sub.10为氢，而且，在R.sub.3，R.sub.5，R.sub.6，R.sub.7和R.sub.10为氢的情况下，R.sub.4另外为公式（2）的基团 ##STR3## 其中R.sub.2，R.sub.8和R.sub.9如上所定义，R.sub.1如下所定义，对于m=1，R.sub.12和R.sub.13独立地为氢，C.sub.1-C.sub.12烷基或苯基，m为1或2，在m为1的情况下，R.sub.1为氢，C.sub.1-C.sub.25脂肪酰基，C.sub.3-C.sub.25烯酰基，被氧，硫或>N--R.sub.16打断的C.sub.3-C.sub.25脂肪酰基；C.sub.6-C.sub.9环烷基羰基，苯基或C.sub.1-C.sub.12烷基取代的苯基，R.sub.16如上所定义，R.sub.6为氢或公式（3）的基团 ##STR4## 其中R.sub.1，R.sub.2，R.sub.3，R.sub.4，R.sub.5，R.sub.7，R.sub.8，R.sub.9和R.sub.10如上所定义，在m为2的情况下，R.sub.1为##STR5## 其中R.sub.17为直接键，C.sub.1-C.sub.18亚烷基，被氧，硫或>N--R.sub.16打断的C.sub.2-C.sub.18亚烷基；C.sub.2-C.sub.18烯基，C.sub.2-C.sub.20烷基亚甲基，C.sub.7-C.sub.20苯基烷基亚甲基，C.sub.5-C.sub.8环烷基，C.sub.7-C.sub.8双环烷基或苯基，R.sub.16如上所定义，R.sub.6为氢，被描述为有机材料的稳定剂，用于防止氧化，热或光诱导降解。
• Mechanophores with a Reversible Radical System and Freezing-Induced Mechanochemistry in Polymer Solutions and Gels
  作者：Keiichi Imato、Atsushi Irie、Takahiro Kosuge、Tomoyuki Ohishi、Masamichi Nishihara、Atsushi Takahara、Hideyuki Otsuka

  DOI：10.1002/anie.201412413

  日期：2015.5.18

  quantitative evaluation of scission of the mechanophores and estimation of mechanical energy induced along polymer chains by external forces. The coagulation of polymer solutions by freezing probably generated force but did not cleave the mechanophores. On the other hand, cross‐linking led to efficient propagation of the force of more than 80 kJ mol−1 to some mechanophores, resulting their cleavage and generation

  聚合物材料中共价键断裂的可视化和定量评估对于理解失效，疲劳和劣化机理以及提高材料的寿命，耐用性，韧性和可靠性非常重要。基于二芳基联苯并呋喃酮的机械基团自由基系统能够通过电子顺磁共振波谱对机械基团的断裂进行原位定量评估，并估计外力沿聚合物链诱导的机械能。通过冷冻使聚合物溶液凝结可能会产生力，但不会使机械分裂。另一方面，交联导致超过80 kJ mol -1的力的有效传播某些机械基团被裂解，并生成有色的稳定基团。这种机械探针的概念也有可能阐明聚合物领域中其他有争议的问题。