2-((benzyloxy)methyl)benzoic acid | 119367-89-4

• 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-((benzyloxy)methyl)benzoic acid
• 英文别名: 2-[(Benzyloxy)methyl]benzoic acid；2-(phenylmethoxymethyl)benzoic acid
• CAS: 119367-89-4
• 化学式: C₁₅H₁₄O₃
• 分子量: 242.274
• InChiKey: VLUBQMSMFFWWPH-UHFFFAOYSA-N

物化性质

• 沸点：
  385.9±22.0 °C(Predicted)
• 密度：
  1.200±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  2-((benzyloxy)methyl)benzoic acid 在 lithium aluminium tetrahydride 、 sodium methylate 、 pyridinium chlorochromate 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 9.0h， 生成 苄甲醚
  参考文献：
  名称：

  Intramolecular generation of oxonium ylides from functionalized arylcarbenes

  摘要：

  DOI：

  10.1021/ja00186a048
• 作为产物：
  描述：

  2-溴苄醇 在 sodium hydride 、 magnesium 、 1,2-二溴乙烷 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.67h， 生成 2-((benzyloxy)methyl)benzoic acid
  参考文献：
  名称：

  Amide-modified prenylcysteine based Icmt inhibitors: Structure–activity relationships, kinetic analysis and cellular characterization

  摘要：

  Human protein isoprenylcysteine carboxyl methyltransferase (hIcmt) is the enzyme responsible for the alpha-carboxyl methylation of the C-terminal isoprenylated cysteine of CaaX proteins, including Ras proteins. This specific posttranslational methylation event has been shown to be important for cellular transformation by oncogenic Ras isoforms. This finding led to interest in hIcmt inhibitors as potential anti-cancer agents. Previous analog studies based on N-acetyl-S-farnesylcysteine identified two prenylcysteine-based low micromolar inhibitors (1a and 1b) of hIcmt, each bearing a phenoxyphenyl amide modification. In this study, a focused library of analogs of 1a and 1b was synthesized and screened versus hIcmt, delineating structural features important for inhibition. Kinetic characterization of the most potent analogs 1a and 1b established that both inhibitors exhibited mixed-mode inhibition and that the competitive component predominated. Using the Cheng-Prusoff method, the K-i values were determined from the IC50 values. Analog 1a has a K-IC of 1.4 +/- 0.2 mu M and a K-IU of 4.8 +/- 0.5 mu M while 1b has a K-IC of 0.5 +/- 0.07 mu M and a K-IU of 1.9 +/- 0.2 mu M. Cellular evaluation of 1b revealed that it alters the subcellular localization of GFP-KRas, and also inhibits both Ras activation and Erk phosphorylation in Jurkat cells. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.087

文献信息

• Chlorobenzene-driven palladium-catalysed lactonisation of benzoic acids
  作者：Masahiro Abe、Akiho Mizukami、Emi Yoshida、Tetsutaro Kimachi、Kiyofumi Inamoto

  DOI：10.1039/d3ra08176a

  日期：——

  Herein, we developed a palladium-catalysed C–H cyclisation of benzoic acids in chlorobenzene without additional oxidants. The key to the success of these reactions is the use of chlorobenzene, which serves a dual role as a solvent and an oxidant, thus providing a simple and efficient method for synthesising phthalides.

  在此，我们开发了一种钯催化苯甲酸在氯苯中的 C-H 环化反应，无需额外的氧化剂。这些反应成功的关键是氯苯的使用，它具有溶剂和氧化剂的双重作用，从而为合成苯酞提供了一种简单有效的方法。
• Metal-Free C(sp³)–H Allylation via Aryl Carboxyl Radicals Enabled by Donor–Acceptor Complex
  作者：Yang Li、Jing Zhang、Defang Li、Yiyun Chen

  DOI：10.1021/acs.orglett.8b01172

  日期：2018.6.1

  The first aryl carboxyl radical generation by the donor-acceptor complex with N-acyloxyphthalimides and Hantzsch esters is reported. Regio- and chemoselective C(sp(3))-H bond allylation is enabled by aryl carboxyl radicals with visible light irradiation under mild and metal-free conditions.
• IMIDAZOLE DERIVATIVES AS PROTEIN KINASE INHIBITORS IN PARTICULAR EGF-R TYROSINE KINASE
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0797575A1

  公开（公告）日：1997-10-01
• [EN] IMIDAZOLE DERIVATIVES AS PROTEIN KINASE INHIBITORS IN PARTICULAR EGF-R TYROSINE KINASE<br/>[FR] DERIVES IMIDAZOLES UTILISES COMME INHIBITEURS DE LA PROTEINE KINASE, NOTAMMENT DE LA TYROSINE KINASE DU RECEPTEUR DU FACTEUR DE CROISSANCE DE L'EPIDERME (EGF-R)
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：WO1996018626A1

  公开（公告）日：1996-06-20

  (EN) Imidazole derivatives of general formula (I), wherein R1-R8 each independently signify hydrogen, lower-alkyl, substituted lower alkyl, lower-alkenyl, lower-alkoxy, substituted lower alkoxy, lower-alkoxycarbonyl, halogen, hydroxy, amino, mono- or di(lower-alkyl)amino or nitro, and pharmaceutically usable salts thereof are protein kinase inhibitors and can be used as medicaments, e.g. for the control of hyperproliferative disorders such as atherosclerosis, psoriasis and tumors as well as of alopecia.(FR) Dérivés imidazoles de la formule générale (I) et leurs sels acceptables sur le plan pharmacologique. Dans cette formule, R1-R8 représentent chacun indépendamment hydrogène, alkyle inférieur, alkyle inférieur substitué, alcényle inférieur, alcoxy inférieur, alcoxy inférieur substitué, alcoxycarbonyle inférieur, halogène, hydroxy, amino, mono ou di(alkyle inférieur)amino ou nitro. Ces dérivés sont des inhibiteurs des protéines kinases et on peut les utiliser en tant que médicaments, par exemple pour lutter contre les désordres excessivement prolifératifs tels que l'athérosclérose, le psoriasis et les tumeurs, de même que l'alopécie.
• [EN] COMPOUNDS AND METHODS FOR USE IN TREATING NEOPLASIA AND CANCER<br/>[FR] COMPOSÉS ET MÉTHODES DE TRAITEMENT D'UNE NÉOPLASIE OU D'UN CANCER
  申请人：PURDUE RESEARCH FOUNDATION

  公开号：WO2013016531A2

  公开（公告）日：2013-01-31

  The present invention relates to a novel method for the treatment of neoplasia, including cancer and other diseases and conditions in humans and mammals. More particularly, in preferred aspects, the present invention provides a method for the use of novel compounds for the treatment of neoplasia, hyperproliferative cell growth including psoriasis, restenosis following cardiovascular surgery, hyperplasia, including renal hyperplasia, chronic inflammatory diseases including rheumatoid and osteoarthritis, among others.