p-[(E)-2-(3,4-dihydro-4,4-dimethyl-2H-1-benzopyran-6-yl)propenyl]benzoic acid | 88579-29-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: p-[(E)-2-(3,4-dihydro-4,4-dimethyl-2H-1-benzopyran-6-yl)propenyl]benzoic acid
• 英文别名: 4-[(E)-2-(4,4-dimethyl-6-chromanyl)-2-methylvinyl]benzoic acid；(E)-p-[2-(4,4-Dimethylchroman-6-yl)propenyl]benzoic Acid；(E)-p-(2-(4,4-Dimethylchroman-6-yl)propenyl)benzoic acid；4-[(E)-2-(4,4-dimethyl-2,3-dihydrochromen-6-yl)prop-1-enyl]benzoic acid
• CAS: 88579-29-7
• 化学式: C₂₁H₂₂O₃
• 分子量: 322.404
• InChiKey: DFQLRIXABZAEHT-WYMLVPIESA-N

物化性质

• 熔点：
  196-197 °C
• 沸点：
  485.9±44.0 °C(Predicted)
• 密度：
  1.146±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  p-[(E)-2-(3,4-dihydro-4,4-dimethyl-2H-1-benzopyran-6-yl)propenyl]benzoic acid 生成 4-[(E)-2-(4,4-dimethyl-2,3-dihydrochromen-6-yl)prop-1-enyl]benzamide
  参考文献：
  名称：

  HOFFMAN, WILLIAM W.;KRASKA, ALLEN R.

  摘要：

  DOI：
• 作为产物：
  描述：

  3-甲基巴豆酰氯 在 吡啶 、 氢氧化钾 、 lithium aluminium tetrahydride 、 三氯化铝 、 15-冠醚-5 、 四氯化锡 、 sodium hydride 、 甲基磺酰氯 作用下， 以 四氢呋喃 、 二硫化碳 、 乙醇 、 二氯甲烷 为溶剂， 反应 88.75h， 生成 p-[(E)-2-(3,4-dihydro-4,4-dimethyl-2H-1-benzopyran-6-yl)propenyl]benzoic acid
  参考文献：
  名称：

  Conformationally restricted retinoids

  摘要：

  A series of conformationally restricted retinoids was synthesized and screened in two assays used to measure the ability of retinoids to control cell differentiation, namely, the reversal of keratinization in tracheal organ culture from vitamin A deficient hamsters and the inhibition of the induction of mouse epidermal ornithine decarboxylase by a tumor promoter. These compounds had bonds corresponding to selected bonds of the E-tetraene chain of retinoic acid (1) held in a planar cisoid conformation by inclusion in an aromatic ring. The meta-substituted analogue 3 of 4-[(E)-2-methyl-4-(2,6,6-trimethylcyclohexenyl)-1,3-butadienyl+ ++]benzoic acid (2) was far less active than 2 in both assays. In contrast, the vinyl homologue of 2 (4) and the 7,8-dihydro and 7,8-methano analogues (5 and 6) had activity comparable to that of 2. Analogues of 4-[(E)-2-(1,1,4,4-tetramethyl-1,2,3,4-tetrahydro-6-naphthyl)propenyl] benzoic acid (7) were also screened. Replacement of the tetrahydronaphthalene ring of 7 by a benzonorbornenyl group (9) significantly reduced activity, as did removal of the vinylic methyl group from 9 (10). Replacement of the propenyl group of 9 by a cyclopropane ring (12) also reduced activity. Replacement of the tetrahydronaphthalene ring of 7 by 4,4-dimethyl-3,4-dihydro-2H-1-benzopyran and -benzothiopyran rings (13 and 14) also decreased activity. Inclusion of the 7,9 double bond system of 1 in an aromatic ring (15 and 16) reduced activity, whereas inclusion of the 5,7 double bond system in an aromatic ring enhanced activity (7 and 19). Inclusion of the 11,13 and 9,11,13 double bond systems in aromatic rings (2 and 18) also reduced activity below that of 1. Retinoic acid, 7, 13, 14, and 19 inhibited papilloma tumor formation in mice. Toxicity testing indicated that 7 was more toxic than 1, 13, 14, and 19, 19 was more toxic than 1, and 13 and 14 were less toxic than 1.

  DOI：

  10.1021/jm00377a022

文献信息

• Synthesis and characterization of selected heteroarotinoids. Pharmacological activity as assessed in vitamin A deficient hamster tracheal organ cultures. Single-crystal x-ray diffraction analysis of 4,4-dimethylthiochroman-6-yl methyl ketone 1,1-dioxide and ethyl (E)-p-[2-(4,4-dimethylthiochroman-6-yl)propenyl]benzoate
  作者：Kristy M. Waugh、K. Darrell Berlin、Warren T. Ford、Elizabeth M. Holt、John P. Carrol、Paul R. Schomber、M. Daniel Thompson、Leonard J. Schiff

  DOI：10.1021/jm00379a021

  日期：1985.1

  reported the first four members of heteroarotinoids, the names of which are ethyl (E)-p-[2-(4,4-dimethylthiochroman-6-yl)propenyl]benzoate (1b), ethyl (E)-p-[2-(4,4-dimethylchroman-6-yl)propenyl]benzoate (1c), ethyl (E)-p-[2-(4,4-dimethyl-1-oxothiochroman-6-yl)propenyl]benzoate (1d), and (E)-p-[2-(4,4-dimethylchroman-6-yl)propenyl]benzoic acid (1e). IR, 1H NMR and 13C NMR data have been recorded for each

  据报道，杂芳烃类化合物的前四个成员，其名称为（E）-对-[2-（4,4-二甲基硫代苯并吡喃-6-基）丙烯基]苯甲酸乙酯（1b），（E）-对-乙基[2-（4,4-二甲基苯并吡喃-6-基）丙烯基]苯甲酸酯（1c），（E）-对-[2-（4,4-二甲基-1-氧代硫代苯并吡喃-6-基）丙烯基]苯甲酸乙酯（ 1d）和（E）-对-[2-（4,4-二甲基苯并吡喃-6-基）丙烯基]苯甲酸（1e）。每种化合物的IR，1H NMR和13C NMR数据均已记录，并支持结构指定。为了为将来类似物的比较提供坚实的基础，对（E）-对-[2-（4,4-二甲基硫代苯并吡喃-6-基）丙烯基]苯甲酸乙酯（1b）的单晶进行了X射线分析）和前体4,4-二甲基硫代苯并六基甲基甲酮1,1-二氧化物（18）。这些关于杂芳烃类化合物1b的数据表明，存在于晶胞中的两个分子的每一个中，两个芳基环系几乎垂直（分别为86.37度和84.17度）。
• Heterocyclic compounds
  申请人：Hoffmann-La Roche Inc.

  公开号：US04678793A1

  公开（公告）日：1987-07-07

  Novel p-[2(4,4-dimethyl-6-heterophenyl)substituted phenyl derivatives and salts thereof which are useful for combatting neoplasms and dermatoses including oral and topical compositions containing said derivatives which are suitable for such uses.

  新型p-[2(4,4-二甲基-6-杂苯基)取代苯基衍生物及其盐，可用于对抗肿瘤和皮肤病，包括含有该衍生物的口服和局部药物组合物，适用于这些用途。
• Method for inhibiting the degradation of cartilage
  申请人：Pfizer Inc.

  公开号：US04808597A1

  公开（公告）日：1989-02-28

  Certain carboxylic acids of the formula ##STR1## and the pharmaceutically-acceptable salts thereof, and certain esters and amides thereof, are useful for inhibiting the degradation of articular cartilage when administered to a mammalian subject afflicted with an arthritic disease. X is O, S, SO, SO.sub.2, NH, NCH.sub.3 or NCOCH.sub.3 ; and n is zero or one.

  当给患有关节炎疾病的哺乳动物主体施用具有以下结构的某些羧酸（##STR1##）及其药用可接受的盐、某些酯和酰胺时，可用于抑制关节软骨的降解。X为O、S、SO、SO.sub.2、NH、NCH.sub.3或NCOCH.sub.3；n为零或一。
• Benzopyranyl and benzothiopyranyl compounds and uses
  申请人：Hoffman-La Roche Inc.

  公开号：US04788213A1

  公开（公告）日：1988-11-29

  Novel p-[2(4,4-dimethyl-6-heterophenyl)substituted phenyl derivatives and salts thereof which are useful for combatting neoplasms and dermatoses including oral and topical compositions containing said derivatives which are suitable for such uses.

  小说p-[2(4,4-二甲基-6-杂环苯基)取代苯基衍生物及其盐，可用于对抗肿瘤和皮肤病，包括口服和局部制剂，其中包含适用于此类用途的衍生物。
• KLAUS, MICHAEL;LOELIGER, PETER
  作者：KLAUS, MICHAEL、LOELIGER, PETER

  DOI：——

  日期：——