(E)-(R)-12-[(3R,5R)-3,5-dihydroxy-cyclohexylidene)-2-hydroxy-2,6-dimethyl-dodec-10-ene-3-one | 432506-87-1

• 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: (E)-(R)-12-[(3R,5R)-3,5-dihydroxy-cyclohexylidene)-2-hydroxy-2,6-dimethyl-dodec-10-ene-3-one
• 英文别名: (E,6R)-12-[(3R,5R)-3,5-dihydroxycyclohexylidene]-2-hydroxy-2,6-dimethyldodec-10-en-3-one
• CAS: 432506-87-1
• 化学式: C₂₀H₃₄O₄
• 分子量: 338.488
• InChiKey: QVXJIOBXFBRYKE-IOSPQCCGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为试剂：
  描述：

  [2-[(3R,5R)-3,5-二[[(叔丁基)二甲基硅烷基]氧基]环己基亚基]乙基]二苯基氧膦 、 正丁基锂 、 、 [(S)-tetrahydro-pyran-2-yloxy]-hexanal 、 氯化铵 在 乙酸乙酯 、 Brine 、 Sodium sulfate-III 、 crude mixture 、 silica gel 、 (E)-(R)-12-[(3R,5R)-3,5-dihydroxy-cyclohexylidene)-2-hydroxy-2,6-dimethyl-dodec-10-ene-3-one 、 tert-butyl-[(1R,3R)-3-[tert-butyl(dimethyl)silyl]oxy-5-[(7R)-7-(oxan-2-yloxy)oct-2-enylidene]cyclohexyl]oxy-dimethylsilane 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 (e)-(r)-8-[(3r,5r)-3,5-Bis-(tert-butyl-dimethyl-silyloxy)-cyclohexylidene]-2-(tetrahydro-pyran-2-yloxy)-oct-6-ene
  参考文献：
  名称：

  Retiferol derivatives and their use in the treatment of skin diseases or conditions associated with photodamage

  摘要：

  本发明涉及公式（I）的视黄醇衍生物：其中X是> C═ CH2或-CH2-; Y和Z独立地是氢、氟或羟基; A是-O（CH2）3-、-（CH2）2-（1,2-C6H4）-、-CH═CH-（1,2-C6H4）-、-C═C-（1,2C6H4）-、-（CH2）2-CO-、-CH2-O-CO-、-CH2NHCO-或-CH2NHCOCH2-; R1是C1-C5烷基; R2和R3独立地是烷基或全氟烷基; R4是氢、羟基、C1-C5烷基或C1-C5烷氧基。本发明使用这些化合物治疗或预防过度增生性皮肤疾病，如银屑病、基底细胞癌、角化病和角化过程障碍;肿瘤性疾病;皮脂腺障碍，如痤疮和脂溢性皮炎;使用这些化合物逆转与光损伤相关的病症，特别是用于经过日晒损伤的皮肤的口服或局部治疗，用于皱纹、弹性过度和过早老化的影响。此外，本发明还涉及一种制备这些化合物的方法以及含有这些化合物的制药组合物。

  公开号：

  US20040077728A1

文献信息

• RETIFEROL DERIVATIVES AND THEIR USE IN THE TREATMENT OF SKIN DISEASES OR CONDITIONS ASSOCIATED WITH PHOTODAMAGE
  申请人：F.HOFFMANN-LA ROCHE AG

  公开号：EP1341745A1

  公开（公告）日：2003-09-10
• [EN] RETIFEROL DERIVATIVES AND THEIR USE IN THE TREATMENT OF SKIN DISEASES OR CONDITIONS ASSOCIATED WITH PHOTODAMAGE<br/>[FR] DERIVES DE RETIFEROL ET LEUR UTILISATION DANS LE TRAITEMENT DE MALADIES DE PEAU OU DE TROUBLES ASSOCIES A DES DOMMAGES PHOTO-INDUITS
  申请人：HOFFMANN LA ROCHE

  公开号：WO2002042247A1

  公开（公告）日：2002-05-30

  Disclosed are retiferol derivatives of formula (I): wherein X is > C=CH2 or -CH2-; Y and Z are independently of each other hydrogen, fluorine or hydroxy; A is -O(CH2)3-, -(CH2)2-(1,2-C6H4)-, -CH=CH-(1,2-C6H4)-, -C=C-(1,2-C6H4)-, -(CH2)2-CO-, -CH2-O-CO-, -CH2NHCO-, or -CH2NHCOCH2-; R1 is C1-C5-alkyl; R?2 and R3¿ are independently of each other alkyl or perfluoroalkyl; and R4 is hydrogen, hydroxy, C1-C5-alkyl or C1-C5-alkyl or C1-C5-alkoxy; the use of such compounds to treat or present hyperproliferative skin diseases such as psoriasis, basal cell carcinomas, disorders of keratinization and keratosis; neoplastic diseases; disorders of the sebaceous glands such as acne and seborrhoic dermatitis; the use of these compounds in reversing the conditions associated with photodamage, particularly for the oral or topical treatment of the skin damaged through sun exposure, the effects of wrinkling, elastosis and premature ageing, furthermore a process for the manufacture of such compounds as well as pharmaceutical compositions containing such compounds.