ethyl 4-[(1E,3E,5E)-4-methyl-6-(2,6,6-trimethylcyclohexen-1-yl)hexa-1,3,5-trienyl]benzoate | 91587-14-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: ethyl 4-[(1E,3E,5E)-4-methyl-6-(2,6,6-trimethylcyclohexen-1-yl)hexa-1,3,5-trienyl]benzoate
• CAS: 91587-14-3
• 化学式: C₂₅H₃₂O₂
• 分子量: 364.528
• InChiKey: HQQNTVZDSWLYMB-ZOVURRQDSA-N

物化性质

• 沸点：
  499.2±24.0 °C(Predicted)
• 密度：
  1.023±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  ethyl 4-[(1E,3E,5E)-4-methyl-6-(2,6,6-trimethylcyclohexen-1-yl)hexa-1,3,5-trienyl]benzoate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以63%的产率得到培维A
  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：

  (7E,9E)-beta-离子亚基乙醛 、 ethyl 4-(diethoxyphosphorylmethyl)benzoate 以37的产率得到ethyl 4-[(1E,3E,5E)-4-methyl-6-(2,6,6-trimethylcyclohexen-1-yl)hexa-1,3,5-trienyl]benzoate
  参考文献：
  名称：

  J. Med. Chem. 1984, 27, 1516-1531

  摘要：

  DOI：

文献信息

• [EN] USE OF HEXATRIENE DERIVATIVES FOR THE MANUFACTURE OF PREPARATIONS FOR TREATING ACNE, PSORIASIS AND LIGHT-INDUCED DAMAGE TO THE SKIN
  申请人：BASF AKTIENGESELLSCHAFT

  公开号：WO1990008760A1

  公开（公告）日：1990-08-09

  (DE) Verwendung von Hexatrienderivaten der Formel (I), worin R1 in der Beschreibung angegebene Bedeutung besitzt, zur Herstellung von pharmaceutischen und kosmetischen Mitteln gegen Akne, Psoriasis und andere mit pathologischer Verhornung einhergehende dermatologische Krankheiten sowie gegen Iatrogen oder durch UV-Licht-Einwirkung bedingte Hautschädigungen, gegen Ekzeme, Warzen, Vitiligo, trockene Augen und andere Corneopathien, ferner gegen Präkanzerosen und Tumoren sowie rheumatische und arthritische Erkrankungen.(EN) Use of hexatriene derivatives of formula (I), where R1 has the meaning given in the description, for the manufacture of pharmaceutical and cosmetic preparations for treating acne, psoriasis and other dermatological diseases accompanied by pathological cornification and for treating iatrogenic skin damage or skin damage caused by the action of UV light, eczema, warts, vitiligo, dry eyes and other corneopathies, as well as precanceroses and tumours, rheumatic and arthritic diseases.(FR) Emploi de dérivés d'hexatriène de formule (I), où R1 a la notation donnée dans la description, pour la fabrication de préparations pharmaceutiques et cosmétiques en vue de traiter l'acné, le psoriasis et d'autres infections dermatologiques s'accompagnant d'une kératinisation pathologique, et pour traiter des lésions dermiques iatrogéniques ou des lésions dermiques provoquées par l'action de la lumière ultraviolette, l'eczéma, les verrues, le vitiligo, les yeux secs et d'autres cornéopathies, ainsi que les précancéroses et les tumeurs, les affections rhumatismales et arthritiques.

  为了将这篇关于六烯三键衍生物在药品和护肤品中用于治疗皮肤疾病的文章从英语翻译成中文，我首先得理解它们的结构和含义。六烯三键衍生物指的是具有特定分子结构的化合物，用于皮肤科药物和护肤品的生产。原文中使用了公式(I)并指定了R1的含义，我需要确保在翻译时准确保留这些技术细节。例如，“Verwendung von Hexatrienderivaten der Formel (I)”翻译为“使用六烯三键衍生物的公式(I)”，其中“六烯三键”指代六碳三烯系统，“衍生物”则计算分子的变体形式。 原文还提到了多种皮肤疾病，如“Acne”、“Psoriasis”、“Eczema”、“Vitiligo”、“Dry Eyes”以及角膜疾病和前癌病变等。我需要使用正确的医学术语来确保翻译的准确性，例如将“Psoriasis”翻译为“银屑病”，“Eczema”翻译为“湿疹”，“Vitiligo”翻译为“vitiligo（皮肤白色 patches orvt重度的皮肤疾病）。此外，”Iatrogen“和”UV-Licht-Einwirkung“翻译为“手术或光照引起”，以反映这些皮肤损害是由人类行为或环境因素引起的。 原文还提到了风湿性疾病和骨关节炎，我需要将其翻译为“风湿性疾病”和“骨关节炎”，确保医疗术语的准确性。例如，”Rheumatische Erkrankungen“翻译为“风湿性疾病”，而“Arthritische Erkrankungen”则翻译为“骨关节炎”。 在确保译文的科学严谨性和专业性的同时，我还要注意保持句子的流畅性和易于理解的特性。由于原文使用了被动语态，我需要检查译文是否同样保持这种方式，以保持文章的专业性。此外，我需要确保任何占位符（如”(I)“）的位置在最终译文中得到正确保留。 最终，我希望通过这一翻译过程，能够准确传达原文中的科学知识和专业内容，同时让读者能够清晰理解六烯三键衍生物在医药和护肤品中的应用及其在治疗多种皮肤病中的用途。
• VERWENDUNG VON HEXATRIENDERIVATEN ZUR HERSTELLUNG VON MITTELN GEGEN AKNE, PSORIASIS UND LICHTSCHÄDEN DER HAUT
  申请人：BASF Aktiengesellschaft

  公开号：EP0413692A1

  公开（公告）日：1991-02-27
• US4804670A
  申请人：——

  公开号：US4804670A

  公开（公告）日：1989-02-14
• Conformationally restricted retinoids
  作者：Marcia I. Dawson、Peter D. Hobbs、Krzysztof Derdzinski、Rebecca L. S. Chan、John Gruber、Wanru Chao、Saundra Smith、Richard W. Thies、Leonard J. Schiff

  DOI：10.1021/jm00377a022

  日期：1984.11

  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.
• J. Med. Chem. 1984, 27, 1516-1531
  作者：

  DOI：——

  日期：——