2-mesitylbenzoic acid | 153868-35-0

• 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: 2-mesitylbenzoic acid
• 英文别名: 2',4',6'-trimethylbiphenyl-2-carboxylic acid；2′,4′,6′-trimethyl-[1,1′-biphenyl]-2-carboxylic acid；2',4',6'-trimethyl[1,1'-biphenyl]-2-carboxylic acid；2-(2,4,6-Trimethylphenyl)benzoic acid
• CAS: 153868-35-0
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: GAQABVRYHABODI-UHFFFAOYSA-N

物化性质

• 熔点：
  183-185 °C(Solv: acetic acid (64-19-7); water (7732-18-5))
• 沸点：
  347.9±11.0 °C(Predicted)
• 密度：
  1.112±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-mesitylbenzoic acid 在 氢氧化钾 、 一水合肼 、 sodium sulfate 、 mercury(II) oxide 作用下， 以 乙醚 、 正丁醇 为溶剂， 反应 108.0h， 生成 (2',4',6'-trimethylbiphenyl-2-yl)phenyldiazomethane
  参考文献：
  名称：

  Intramolecular reactivity of arylcarbenes: Biphenyl-2-ylcarbenes

  摘要：

  Biphenyl-2-ylcarbenes, 2-ArC(6)H(4)CR, were generated photolytically and thermally from diazo precursors. Cyclization, leading to fluorenes, competes with capture of the carbenes by methanol but proceeds faster than intramolecular hydrogen shifts (with R = Me) and intermolecular C-H insertion reactions (with R = H in cyclohexane). By comparison of product ratios with kinetic data for related carbenes from the literature, the cyclization rate is estimated as ca 10(11) s(-1). The intramolecular reactivity of biphenyl-2-ylcarbenes is nor significantly attenuated by variation of R (R = H, Me, Ph). Very minor effects of triplet sensitization and methanol quenching indicate that fluorenes arise from spin-equilibrated biphenyl-2-ylcarbenes, presumably from the singlet state. When Ar = mesityl, the carbene predominantly inserts into C-H bonds of the 2'-methyl groups, giving rise to a dihydrophenanthrene. Formation of a fluorene derivative, by formal insertion into C-C bonds, occurs as a minor process. This unprecedented reaction points to intervention of an o-xylylene in which the methyl group migrates. Laser flash photolysis (LFP) of 2-PhC(6)H(4)CN(2)Ph generates a transient absorption which is due to the T-0-->T-n transition of 9-phenylfluorene rather than to the presumed o-xylylene. On LFP of 2-ArC(6)H(4)CN(2)Ph in trifluoroethanol-acetonitrile, protonation of the carbenes gives rise to carbocations, 2-ArC(6)H(4)CH(+)Ph. The transient absorption spectra of these cations are strongly influenced by twisting about the Ar-Ar bond (Ar = Ph < o-tolyl < mesityl) whereas the rates of nucleophilic capture vary only slightly. Biphenyl-2-ylcarbenium ions (Ar = R = Ph) cyclize more slowly than the analogous carbenes, by a factor of greater than or equal to 10(4).

  DOI：

  10.1002/(sici)1099-1395(199609)9:9<598::aid-poc825>3.0.co;2-l
• 作为产物：
  描述：

  2,6-diisopropylphenyl 2-methoxybenzoate 在 氢氧化钾 作用下， 以 乙醚 、 乙醇 、 苯 为溶剂， 反应 14.5h， 生成 2-mesitylbenzoic acid
  参考文献：
  名称：

  芳基格氏试剂通过 2-甲氧基苯甲酸酯的亲核芳香取代反应方便地合成联苯-2-羧酸

  摘要：

  Nucleophilic aromatic substitution (SNAr) of 2-methoxybenzoic esters derived from 2,6-dialkylphenols by aryl Grignard reagents affords 1,1′-biphenyl-2-carboxylates in excellent yields by proper choice of the bulk of the 2,6-dialkyl-取代基。通过用乙醇水溶液（2,4,6-三甲基苯基和2,6-二异丙基苯基酯）中的氢氧化钾或甲苯中的甲醇钠处理，苯氧基保护基团可以很容易地从生成的联苯-2-羧酸酯中去除，生成游离酸。六甲基磷酰胺（2,6-二叔丁基-4-甲基苯基酯）。通过 SNAr 过程的区域选择性联苯偶联反应被用于正式合成大麻酚中联苯骨架的关键步骤构建。

  DOI：

  10.1246/bcsj.66.3034
• 作为试剂：
  描述：

  1-甲基吲哚 、 溴苯 在 palladium diacetate 、 potassium carbonate 、 2-mesitylbenzoic acid 、 tricyclohexylphosphine tetrafluoroborate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 12.0h， 生成 1-甲基-3-苯基-1H-吲哚 、 1-甲基-2-苯基吲哚
  参考文献：
  名称：

  Exploration of Biaryl Carboxylic Acids as Proton Shuttles for the Selective Functionalization of Indole C–H Bonds

  摘要：

  A survey of diversely substituted 2-arylbenzoic acids were synthesized and tested for use as proton shuttle in the direct arylation of indoles with bromobenzenes. It was found that 3-ethoxy-2-phenylbenzoic acid gives superior yield and selectivity for this class of substrates.

  DOI：

  10.1021/acs.joc.8b00417

文献信息

• [EN] BIPHENYL DERIVATIVE OR ITS SALT, AND PESTICIDE CONTAINING IT AS AN ACTIVE INGREDIENT<br/>[FR] DERIVE DE DIPHENYLE OU SES SELS, ET PESTICIDE DONT IL CONSTITUE LE PRINCIPE ACTIF
  申请人：ISHIHARA SANGYO KAISHA

  公开号：WO2005044007A1

  公开（公告）日：2005-05-19

  A pesticide having stabilized high pesticidal effects for crop plants infected with plant diseases, is presented. The pesticide contains a biphenyl derivative represented by the formula (I) or its salt, as an active ingredient: wherein X, Y and Z are each independently a halogen atom, a hydroxyl group, a formyl group, an alkyl group which may be substituted, an alkoxy group which may be substituted, an alkylthio group, an alkylsulfonyl group, an alkylsulfinyl group, or the like, A is a carbonyl group, a thiocarbonyl group, an alkylene group, or a single bond, R1 and R2 are each independently a hydrogen atom, an alkyl group which may be substituted, an alkenyl group which may be substituted, an alkynyl group which may be substituted, an aryl group which may be substituted, a formyl group, an alkylcarbonyl group, a cyano group, or the like, and m and n are each independently 0, 1, 2, 3 or 4.

  一种对感染植物病害的作物植物具有稳定高效杀虫效果的杀虫剂被提出。该杀虫剂含有作为活性成分的二苯基衍生物，该衍生物由公式(I)表示或其盐类：其中X、Y和Z各自独立为卤素原子、羟基、甲酰基、可能被取代的烷基、可能被取代的烷氧基、烷硫基、烷基亚磺酰基、烷基亚磺酰基或类似基团，A为羰基、硫羰基、亚烷基或单键，R1和R2各自独立为氢原子、可能被取代的烷基、可能被取代的烯基、可能被取代的炔基、可能被取代的芳基、甲酰基、烷基羰基、氰基或类似基团，而m和n各自独立为0、1、2、3或4。
• Synthesis and Characterization of Orally Active Nonpeptide Vasopressin V2 Receptor Antagonists.
  作者：Takehiko OHKAWA、Tatsuya ZENKOH、Masayuki TOMITA、Naomi HOSOGAI、Keiji HEMMI、Hirokazu TANAKA、Hiroyuki SETOI

  DOI：10.1248/cpb.47.501

  日期：——

  novel series of 2,6-diaza-5-oxobicyclo[5.4.0]undeca-1(7),8,10-triene derivatives exhibited antagonistic activity for vasopressin V1 and V2 receptors. Most of these compounds were synthesized and showed a high affinity potential for V2 receptor and low to moderate affinity potential for V1 receptor. The most potent and V2-selective compound, N-[4-[2,6-diaza-6-[2-(4-methylpiperazinyl)-2-oxoethyl] -5- oxobicyclo[5

  进行本研究以评估新系列的2,6-二氮杂-5-氧代双环[5.4.0] undeca-1（7），8,10-三烯衍生物是否表现出对血管加压素V1和V2受体的拮抗活性。这些化合物大多数都是合成的，对V2受体显示出高亲和力，对V1受体显示出低至中等的亲和力。最有效和V2选择性的化合物N- [4- [2,6-二氮杂-6- [2-（4-甲基哌嗪基）-2-氧代乙基] -5-氧代双环[5.4.0] undeca-1（7 ），8,10-三烯-2-基]-羰基]苯基1] [2-（4-甲基苯基）苯基]-甲酰胺（11b），对V2受体表现出2.9 nM的IC50，对于V1受体表现出200 nM的IC50 ， 分别。当对大鼠口服给药时，11b与对照大鼠相比，尿量增加了约18倍。
• Photocatalytic Dehydroxymethylative Arylation by Synergistic Cerium and Nickel Catalysis
  作者：Yuegang Chen、Xin Wang、Xu He、Qing An、Zhiwei Zuo

  DOI：10.1021/jacs.1c00618

  日期：2021.4.7

  broad range of free alcohols and aromatic halides can be facilely employed in this transformation, representing a new paradigm for the C(sp3)–C(sp2) bond construction between free alcohols and aryl halides with the extrusion of formaldehyde. Moreover, mechanistic investigations have been conducted, leading to the identification of a tribenzoate cerium(III) complex as a viable intermediate.

  在使用廉价铈和镍催化剂的温和反应条件下，现在可以将容易获得的游离醇用作选择性 C(sp 3 )–C(sp 2 ) 交叉偶联中操作简单且稳健的碳亲核试剂。在自动化高通量实验的推动下，空间位阻的苯甲酸酯配体已被确定为强大的铈配合物，使铈催化在新兴的金属光氧化还原催化中的协同合作成为可能。广泛的游离醇和芳族卤化物可以轻松地用于这种转化，代表了 C(sp 3 )–C(sp 2) 游离醇和芳基卤之间的键结构与甲醛的挤出。此外，还进行了机理研究，确定了三苯甲酸铈 (III) 配合物作为可行的中间体。
• Multifunctionalized polyethylene glycol derivative and preparation method therefor
  申请人：XIAMEN SINOPEG BIOTECH CO., LTD.

  公开号：US11324827B2

  公开（公告）日：2022-05-10

  Disclosed are a multifunctionalized polyethylene glycol derivative and a preparation method therefor. The derivative has an H-shaped structure as represented by formula (1) and comprises one linear core LPEG and four PEG branch chains, where n1, n2, n3, and n4 respectively are the degrees of polymerization of the branch chains, U1 and U2 are trivalent branching groups connecting the core LPEG to two of the PEG branch chains, F1 and F2 contain a functional group or a protected form R01 thereof and may or may not contain a branched group G, correspondingly, the number of R01 is one or more, F1 and F2 are either identical or different, any one linking group in the molecule or any linking group formed with an adjacent heteroatom group can either remain stable or be degraded, and any one PEG segment in the molecule is discretely polydispersed or monodispersed. The multifunctional polyethylene glycol is flexible and diverse in terms of branch structures and the lengths of branching arms, has various parameters and performance indicators that are adjustable and easy to control, and has a broad applicability.

  本发明公开了一种多功能聚乙二醇衍生物及其制备方法。该衍生物具有由式（1）表示的 H 型结构，包括一个线性核心 LPEG 和四个 PEG 支链，其中 n1、n2、n3 和 n4 分别为支链的聚合度，U1 和 U2 为连接核心 LPEG 和两个 PEG 支链的三价支化基团、F1 和 F2 含有一个官能团或其保护形式 R01，可以含有或不含有支链基团 G，相应地，R01 的数目为一个或多个，F1 和 F2 要么相同要么不同，分子中的任何一个连接基团或与相邻杂原子基团形成的任何连接基团要么保持稳定，要么降解，分子中的任何一个 PEG 段离散多分散或单分散。多功能聚乙二醇的支链结构和支臂长度灵活多样，各种参数和性能指标可调且易于控制，具有广泛的适用性。
• An improved protocol for ligandless Suzuki–Miyaura coupling in water
  作者：Dmitrii N. Korolev、Nikolay A. Bumagin

  DOI：10.1016/j.tetlet.2006.04.039

  日期：2006.6

  Using a reverse order of addition of reagents, PdCl2 and Pd(OAc)(2) are efficient catalysts for the Suzuki-Miyaura reactions in water. The ligandless and mild conditions, the high stability of the catalytic system, short reaction time and good to excellent yields are important features of this protocol. (c) 2006 Published by Elsevier Ltd.