4,4-二甲基-6-乙酰基苯并二氢吡喃 | 88579-19-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 4,4-二甲基-6-乙酰基苯并二氢吡喃
• 英文名称: 4,4-Dimethylchroman-6-yl Methyl Ketone
• 英文别名: 6-acetyl-4,4-dimethyl-chroman；4,4-dimethyl-6-acetylchromane；1-(4,4-dimethylchroman-6-yl)ethanone；4,4-dimethyl-6-acetylchroman；1-(4,4-dimethyl-2,3-dihydrochromen-6-yl)ethanone
• CAS: 88579-19-5
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: APBGIHIRYOFIJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  4,4-二甲基-6-乙酰基苯并二氢吡喃 在 溴 、 sodium 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 6.0h， 生成 ethyl 2-acetyl-4-(4,4-dimethylchroman-6-yl)-4-oxobutanoate
  参考文献：
  名称：

  [EN] PYRROLE DERIVATIVES USED AS MODULATORS OF ALPHA7 NACHR
  [FR] DÉRIVÉS DE PYRAZOLE UTILISÉS COMME MODULATEURS DE NACHR ALPHA-7

  摘要：

  本发明涉及公式I的吡咯衍生物作为尤其是α7亚型的尼古丁型乙酰胆碱受体调节剂。该发明包括吡咯衍生物、类似物、它们的前药、同位素、代谢物、药学上可接受的盐、多型体、溶剂合物、光学异构体、包合物、与适当药物的组合以及其药物组合物。本发明还包括所述化合物的制备方法和预期在治疗中的使用。由于吡咯衍生物对尼古丁型乙酰胆碱受体的调节活性，该发明在涉及中枢和外周神经系统中胆碱传递的参与的疾病的预防和治疗中找到应用。该发明涉及吡咯衍生物调节胆碱传递和内源神经递质ACh通过尼古丁型乙酰胆碱受体特别是α7亚型的效能的能力。

  公开号：

  WO2012104782A1
• 作为产物：
  描述：

  3-甲基巴豆酰氯 在 吡啶 、 lithium aluminium tetrahydride 、 三氯化铝 、 四氯化锡 、 sodium hydride 、 甲基磺酰氯 作用下， 以 四氢呋喃 、 二硫化碳 、 二氯甲烷 为溶剂， 反应 72.17h， 生成 4,4-二甲基-6-乙酰基苯并二氢吡喃
  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）。
• Disubstituted acetylenes bearing heteroaromatic and heterobicyclic
  申请人：Allergan

  公开号：US05602130A1

  公开（公告）日：1997-02-11

  Retinoid-like activity is exhibited by compounds of the formula ##STR1## where X is S, O, or NR' where R' is hydrogen or lower alkyl; R is hydrogen or lower alkyl; A is pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl or pyrazinyl; n is 0-4; and B is H, --COOH or a pharmaceutically acceptable salt, ester or amide thereof, --CH.sub.2 OH or an ether or ester derivative, or --CHO or an acetal derivative, or --COR.sub.1 or a ketal derivative where R.sub.1 is --(CH.sub.2).sub.m CH.sub.3 where m is 0-4, or a pharmaceutically acceptable salt thereof.

  化合物具有类似视黄醇的活性，其化学式为##STR1##其中X为S、O或NR'，R'为氢或较低的烷基；R为氢或较低的烷基；A为吡啶基、噻吩基、呋喃基、吡啶并嗪基、嘧啶基或吡嗪基；n为0-4；B为H、--COOH或其药学上可接受的盐、酯或酰胺，--CH.sub.2 OH或醚或酯衍生物，或--CHO或缩醛衍生物，或--COR.sub.1或缩酮衍生物，其中R.sub.1为--(CH.sub.2).sub.m CH.sub.3，m为0-4，或其药学上可接受的盐。
• Acetylenes disubstituted with a phenyl group and a heterobicyclic group
  申请人：Allergan, Inc.

  公开号：US04810804A1

  公开（公告）日：1989-03-07

  Retinoid-like activity is exhibited by compounds of the formula ##STR1## where X is S, O or NR.sub.1 where R.sub.1 is hydrogen or lower alkyl; n is 0-5; R is H or lower alkyl and A is H, --COOH or a pharmaceutically acceptable salt, ester or amide thereof, --CH.sub.2 OH or an ether or ester derivative thereof, or --CHO or an acetal derivative thereof, or --COR.sub.2 or a ketal derivative thereof where R.sub.2 is --(CH.sub.2).sub.m CH.sub.3 where m is 0-4; or a pharmaceutically acceptable salt.

  化合物的结构式为 ##STR1## 其中X为S、O或NR.sub.1，其中R.sub.1为氢或较低的烷基；n为0-5；R为H或较低的烷基，A为H、--COOH或其药用可接受的盐、酯或酰胺，--CH.sub.2 OH或其醚或酯衍生物，或--CHO或其缩醛衍生物，或--COR.sub.2或其缩酮衍生物，其中R.sub.2为--(CH.sub.2).sub.m CH.sub.3，其中m为0-4；或其药用可接受的盐。
• CHROMAN-SUBSTITUTED, TETRAHYDROQUINOLINE-SUBSTITUTED AND THIOCHROMAN-SUBSTITUTED HETEROAROTINOIDS AS ANTI-CANCER AGENTS
  申请人：THE BOARD OF REGENTS FOR OKLAHOMA STATE UNIVERSITY

  公开号：US20200062711A1

  公开（公告）日：2020-02-27

  Chemical compounds that inhibit cancer cell growth are provided. The compounds are heteroarotinoids and derivatives thereof with oxygen, nitrogen or sulfur in chroman systems, tetrahydroquinoline systems, and tetrahydrothiochroman systems.

  提供了抑制癌细胞生长的化合物。这些化合物是杂环维生素A类化合物及其衍生物，其在色酮系统、四氢喹啉系统和四氢硫色酮系统中含有氧、氮或硫。
• 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。