6-acetyl-1,4-methano-1,2,3,4-tetrahydronaphthalene | 4228-39-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 6-acetyl-1,4-methano-1,2,3,4-tetrahydronaphthalene
• 英文别名: 6-Acetyl-benzonorbornen；1-(4-Tricyclo[6.2.1.02,7]undeca-2(7),3,5-trienyl)ethanone
• CAS: 4228-39-1
• 化学式: C₁₃H₁₄O
• 分子量: 186.254
• InChiKey: SWIHOQNXAHGRLA-UHFFFAOYSA-N

物化性质

• 沸点：
  318.4±31.0 °C(Predicted)
• 密度：
  1.118±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-acetyl-1,4-methano-1,2,3,4-tetrahydronaphthalene 在 sodium hypobromide 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 以94%的产率得到1,4-methano-1,2,3,4-tetrahydro-6-naphthalenecarboxylic 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
• 作为产物：
  描述：

  1,4-二氢-1,4-甲桥萘 在 palladium on activated charcoal 三氯化铝 、 氢气 作用下， 以 乙醇 、 1,2-二氯乙烷 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 21.0h， 生成 6-acetyl-1,4-methano-1,2,3,4-tetrahydronaphthalene
  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

• A method for the stereoselective synthesis of (E)-methylstilbene retinoids
  作者：Marcia I. Dawson、Krzysztof Derdzinski、Peter D. Hobbs、Rebecca L. C. Chan、Sung W. Rhee、Dennis Yasuda

  DOI：10.1021/jo00200a055

  日期：1984.12
• ——
  作者：LANG G.、 MAIGNAN J.、 RESTLE S.、 SHROOT B.

  DOI：——

  日期：——
• BENZONORBORNENYL, BENZOPYRANYL AND BENZOTHIOPYRANYL RETINOIC ACID ANALOGUES
  申请人：SRI INTERNATIONAL

  公开号：EP0155940A1

  公开（公告）日：1985-10-02
• INHIBITORS OF HISTONE DEACETYLASE USEFUL FOR THE TREATMENT OR PREVENTION OF HIV INFECTION
  申请人：Merck Sharp & Dohme Corp.

  公开号：US20210403479A1

  公开（公告）日：2021-12-30

  The present invention relates to Compounds of Formula I: and pharmaceutically acceptable salts or prodrug thereof, wherein R 1 , R 2 , R 3 , R 4 and A are as defined herein. The present invention also relates to compositions comprising at least one compound of Formula I, and methods of using the compounds of Formula I for treating or preventing HIV infection in a subject.
• [EN] BENZONORBORNENYL, BENZOPYRANYL AND BENZOTHIOPYRANYL RETINOIC ACID ANALOGUES
  申请人：SRI INTERNATIONAL

  公开号：WO1985000806A1

  公开（公告）日：1985-02-28

  (EN) Compounds of the formulas (I), (II) and (III), where R1, R2, R3 and R4 are hydrogen or methyl, X is hydrogen or fluorine and Q is formula (IV), (V), (VI), (VII), (VIII), or (IX), and X1 is hydrogen, hydroxy, methoxy or fluorine, R is hydroxy, alkoxy with 0 or 1 hydroxy substituent, aroxy or NR5R6, where R5 is hydrogen, alkyl with 0 or 1 hydroxy substituent or aryl, and R6 is alkyl with 0 or 1 hydroxy substituent or aryl, with the provisos that X is fluorine only when R2 is methyl, when R3 or R4 is methyl the other R3 or R4 is also methyl and when Q is said thienyl group Q may be in either the cis or trans position. These compounds are useful as chemopreventive agents for inhibiting tumor promotion in epithelial cells and for treating nonmalignant skin disorders. (FR) Composés de formules (I), (II) et (III), où R1, R2, R3 et R4 représentent un hydrogène ou un méthyle, X représente un hydrogène ou un fluor et Q représente (IV), (V), (VI), (VII), (VIII) ou (IX) et X1 représente un hydrogène, un hydroxy, un méthoxy ou un fluor, R représente un hydroxy, un alkoxy avec 0 ou 1 substituant hydroxy, un aroxy ou NR5R6, où R5 représente un hydrogène, un alcoyle avec 0 ou 1 substituant hydroxy ou un aryle, et R6 représente un alcoyle avec 0 ou 1 substituant hydroxy ou un aryle, à condition que X ne représente un fluor que lorsque R2 est un méthyle, lorsque R3 ou R4 est un méthyle, l'autre R3 ou R4 étant également un méthyle et lorsque Q est un groupe thiényle, Q pouvant être en position cis ou trans. Ces composés sont utiles comme agents chimiopréventifs pour inhiber l'activation tumorale dans des cellules épithéliales et pour traiter des affections cutanées non malignes.