o-terphenyl-4'-carboxylic acid methyl ester | 77218-89-4

• 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: o-terphenyl-4'-carboxylic acid methyl ester
• 英文别名: o-Terphenyl-4'-carbonsaeure-methylester；3,4-diphenylbenzoic acid methyl ester；Methyl 3,4-diphenylbenzoate
• CAS: 77218-89-4
• 化学式: C₂₀H₁₆O₂
• 分子量: 288.346
• InChiKey: ZRRTVIXUNGKPCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  o-terphenyl-4'-carboxylic acid methyl ester 在 lithium aluminium tetrahydride 、 重铬酸吡啶 作用下， 生成 (1,1':2',1''-terphenyl)-4'-carbaldehyde
  参考文献：
  名称：

  Miyamae, Tetsuhisa; Hashizume, Hirokazu; Ogawa, Tadashi, Arzneimittel-Forschung/Drug Research, 1997, vol. 47, # 1, p. 13 - 18

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 3,4-diphenyl-3-cyclohexenecarboxylate 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 1.33h， 以97%的产率得到o-terphenyl-4'-carboxylic acid methyl ester
  参考文献：
  名称：

  1-异亚丙基-4,4-二苯基-2,5-环己二烯的外-1,2-二氧杂环丁烷衍生物的酸催化重排

  摘要：

  结果表明，1,2-二氧杂环丁烷衍生物，3,3-二甲基-7,7-二苯基-1-2-二氧杂螺[3.5]壬-5,8-二烯的酸催化分解，从1-异亚丙基得到-4,4-二苯基-2,5-环己二烯，得到 1-甲基-1-(邻三联苯-4'-基)乙基氢过氧化物，双[1-甲基-1-(邻三联苯-4'-基) ) 乙基] 过氧化物、1-(1-hydroperoxy-1-methylethyl)-4,4-diphenylcyclohexa-2,5-dien-1-ol 和 o-terphenyl-4'-ol，以及通常的二氧杂环丁烷裂解产物，4,4-二苯基-2,5-环己二烯酮。这些产品的分布和产率取决于所用的酸性试剂和/或条件。

  DOI：

  10.1246/bcsj.53.3279

文献信息

• Substituted n-[(pyridyl)alkyl]aryl-carboxamide
  申请人：Hoffmann-La Roche Inc.

  公开号：US04916145A1

  公开（公告）日：1990-04-10

  The invention relates to compounds of the formula ##STR1## wherein *B is ##STR2## Y is O or S, *A is *--(CH.sub.2).sub.n --(X).sub.m --(CH.sub.2).sub.r --, n or r, independently, are integers from 0 to 3, m is an integer from 0 to 1, provided that when m is 1, then n must be at least 1, X is O or S, R.sub.1 and R.sub.4, independently, are hydrogen, lower alkyl, hydroxy or lower alkoxy, provided that when *B is other than ##STR3## at least one of R.sub.1 and R.sub.4, and one of R.sub.6 and R.sub.7 must be hydrogen, R.sub.2 and R.sub.3 are independently hydrogen, lower alkyl, cycloalkyl, halogen, nitro, lower alkoxy, lower alkenyl, lower alkynyl or aryl, R.sub.5 and R.sub.6, independently are hydrogen or lower alkyl, R.sub.7 is hydrogen, lower alkyl, cycloalkyl or aryl, Het is a monocyclic 5- or 6-membered hetero aromatic or a bicyclic heteroaromatic radical containing one or two hetero atoms selected from nitrogen oxygen and sulfur, which radical may be substituted by lower alkyl, halogen or aryl, and the asterisk denotes the point of attachment, and when R.sub.6 and R.sub.7 are different, their enantiomers and racemic mixtures thereof, and pharmaceutical acceptable acid addition salts thereof. The compounds of formula I exhibit activity as Platelet Activating Factor (PAF) antagonists and are, therefore, useful as agents for the prevention and treatment of vascular diseases, pulmonary diseases, dermatological disorders, transplant rejection, immunological disorders and inflammatory conditions.

  该发明涉及以下式的化合物##STR1##其中*B为##STR2##Y为O或S，*A为*--(CH.sub.2).sub.n --(X).sub.m --(CH.sub.2).sub.r --，n或r独立地为0到3的整数，m为0到1的整数，但当m为1时，n必须至少为1，X为O或S，R.sub.1和R.sub.4独立地为氢、较低的烷基、羟基或较低的烷氧基，但当*B不是##STR3##时，R.sub.1和R.sub.4中至少一个，以及R.sub.6和R.sub.7中的一个必须为氢，R.sub.2和R.sub.3独立地为氢、较低的烷基、环烷基、卤素、硝基、较低的烷氧基、较低的烯基、较低的炔基或芳基，R.sub.5和R.sub.6独立地为氢或较低的烷基，R.sub.7为氢、较低的烷基、环烷基或芳基，Het为含有一或两个异原子（从氮、氧和硫中选择）的单环5-或6-成员杂芳基或含有一个或两个异原子的双环杂芳基，该基团可以被较低的烷基、卤素或芳基取代，星号表示连接点，当R.sub.6和R.sub.7不同时，它们的对映异构体和外消旋混合物，以及其药学上可接受的酸盐。式I的化合物表现为血小板活化因子（PAF）拮抗剂的活性，因此，它们可用作预防和治疗血管疾病、肺部疾病、皮肤病、移植排斥、免疫紊乱和炎症症状的药物。
• New route to o-terphenyls: application to the synthesis of 6,7,10,11-tetramethoxy-2-(methoxycarbonyl)triphenylene
  作者：Elisabetta Brenna、Claudio Fuganti、Stefano Serra

  DOI：10.1039/a707738f

  日期：——

  The hydroxy-o-terphenylcarboxylic acid esters 6a–f have been prepared by benzannulation of the 5,6-diaryl-3-methoxycarbonylhexa-3,5-dienoic acids 5a–f using triethylamine–ethyl chloroformate. The application of this new synthesis of triphenylenes is illustrated through the synthesis of 2-methoxycarbonyl-6,7,10,11-tetramethoxytriphenylene 9.

  羟基-o-三苯甲酸酯6a–f是通过使用三乙胺-氯仿酸乙酯对5,6-二芳基-3-甲氧基羧基六烯酸5a–f进行苯环化反应合成的。这种新型三苯烯合成方法的应用通过合成2-甲氧基羧基-6,7,10,11-四甲氧基三苯烯9得以展示。
• A Convenient Synthesis of Methyl 4-Substituted Benzoates via Diels-Alder Reaction in the Presence of Palladium on Activated Carbon
  作者：Yoh-ichi Matsushita、Kei Sakamoto、Taro Murakami、Takanao Matsui

  DOI：10.1080/00397919408010254

  日期：1994.12

  The thermal reaction of methyl 2-oxo-2H-pyran-5-carboxylates with substituted styrenes in the presence of 10% palladium on activated carbon afforded directly the corresponding methyl 4-biphenylcarboxylates in good yields. By the similar procedure, methyl 4-heteroaryl- and 4-alkyl-substituted benzoates were obtained from heteroaromatic olefins and alkenes, respectively.
• An efficient synthesis of o-terphenyls from Morita–Baylis–Hillman adducts of cinnamaldehydes: a consecutive bromination, Wittig reaction, 6π-electrocyclization, and an aerobic oxidation process
  作者：Cheol Hee Lim、Sung Hwan Kim、Ko Hoon Kim、Jae Nyoung Kim

  DOI：10.1016/j.tetlet.2013.02.104

  日期：2013.5

  An efficient synthetic method of o-terphenyls was developed from Morita-Baylis-Hillman adducts. The synthesis was carried out via a sequential bromination of MBH adducts, Wittig reaction with various aldehydes, 6 pi-electrocyclization, and a base-mediated aerobic oxidation process. (C) 2013 Elsevier Ltd. All rights reserved.
• Diels-Alder reactions of 2-pyrones. Direction of the addition reaction with acetylenes
  作者：Joe A. Reed、Curtis L. Schilling、R. F. Tarvin、Thomas A. Rettig、John K. Stille

  DOI：10.1021/jo01259a035

  日期：1969.7