7,11-dimethyl-3-oxo-dodeca-6ξ,10-dienoic acid ethyl ester | 56523-11-6

• 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: 7,11-dimethyl-3-oxo-dodeca-6ξ,10-dienoic acid ethyl ester
• 英文别名: 7,11-Dimethyl-3-oxo-dodeca-6ξ,10-diensaeure-aethylester；Ethyl 7,11-dimethyl-3-oxododeca-6,10-dienoate
• CAS: 56523-11-6
• 化学式: C₁₆H₂₆O₃
• 分子量: 266.381
• InChiKey: NNGNVDPEUNRSJJ-UHFFFAOYSA-N

物化性质

• 沸点：
  373.5±30.0 °C(Predicted)
• 密度：
  0.951±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-苯基双(三氟甲烷磺酰)亚胺 、 7,11-dimethyl-3-oxo-dodeca-6ξ,10-dienoic acid ethyl ester 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 以58%的产率得到Ethyl 7,11-dimethyl-3-(trifluoromethylsulfonyloxy)dodeca-2,6,10-trienoate
  参考文献：
  名称：

  Elucidation of the mechanism producing menaquinone-4 in osteoblastic cells

  摘要：

  Vitamin K is an essential nutrient and a cofactor for the carboxylation of specific glutamyl residues of proteins to gamma-glutamyl residues, which activates osteocalcin related to bone formation. Among vitamin K homologues, menaquinone-4 (MK-4) is the most active biologically, up-regulating the gene expression of bone markers, and thus has been clinically used in the treatment of osteoporosis in Japan. Recently, we confirmed that MK-4 was converted from dietary phylloquinone (PK), and then accumulated in various tissues at high concentrations. This system should play an important role in biological functions including bone formation, however, the pathway by which MK- 4 is converted remains unclear. In this study, we studied the mechanism of MK-4's conversion with chemical techniques using deuterated analogues. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.01.021
• 作为产物：
  描述：

  1,3-丙酮二羧酸二乙酯 、 alkaline earth salt of/the/ methylsulfuric acid 在 aluminum isopropoxide 作用下， 生成 7,11-dimethyl-3-oxo-dodeca-6ξ,10-dienoic acid ethyl ester
  参考文献：
  名称：

  Teisseire et al., Recherches, 1956, # 6, p. 30,35

  摘要：

  DOI：

文献信息

• Novel prenyl transferase inhibitors
  申请人：——

  公开号：US20040121985A1

  公开（公告）日：2004-06-24

  Farnesyl diphosphate analogs, specifically the 3-substituted alcohol precursors of the diphosphate analogs, 3-allylfarnesol and 3-vinylfarnesol, are potent inhibitors of mammalian protein fanesyltransferase (FTase). 3-allylgeranylgeraniol is a highly specific cellular inhibitor of protein geranylgeranylation (GGTase I). Furthermore, these compounds are able to efficiently block the anchorage-dependent growth of ras transformed cells. While 3-allylfarnesol inhibits protein farnesylation in situ, 3-vinylfarnesol instead leads to the abnormal prenylation of proteins with the 3-vinylfarnesyl group. In a similar manner, treatment with 3-allylgeranylgeraniol inhibits protein geranylgeranylation while 3-vinylgeranylgeraniol restores protein geranylgeranylation in cells.

  法尼基二磷酸类似物，特别是3-取代醇前体的二磷酸类似物，3-烯丙基法尼醇和3-乙烯基法尼醇，是哺乳动物蛋白质法尼基转移酶（FTase）的强效抑制剂。3-烯丙基戊二醇是蛋白质戊二烯基化（GGTase I）的高度特异性细胞抑制剂。此外，这些化合物能够有效地阻止ras转化细胞的附着依赖性生长。虽然3-烯丙基法尼醇在原位抑制蛋白质法尼基化，但3-乙烯基法尼醇却导致蛋白质异常前醇化，其中含有3-乙烯基法尼基基团。以类似的方式，使用3-烯丙基戊二醇处理可以抑制蛋白质戊二烯基化，而3-乙烯基戊二醇可以恢复细胞中蛋白质的戊二烯基化。
• Novel .beta.-ketone compounds
  申请人：Roussel-UCLAF

  公开号：US04028386A1

  公开（公告）日：1977-06-07

  Novel .beta.-ketone compounds of the formula ##STR1## wherein R is a linear or branched alkyl of 4 to 10 carbon atoms optionally containing a double bond or an epoxy and optionally substituted with a branched or linear alkoxy of 1 to 3 carbon atoms, Z is selected from the group consisting of --CH=CH--, --CHOH--CH=CH--, ##STR2## and --OCH.sub.2 --, X is selected from the group consisting of hydrogen and methyl, Y is selected from the group consisting of linear and branched alkoxy of 1 to 5 carbon atoms and ##STR3## and R' and R" are linear or branched alkyl of 1 to 4 carbon atoms which are insecticides and their preparation.

  化合物的式子为 ##STR1## 其中 R 是4到10个碳原子的线性或支链烷基，可选含有双键或环氧基，并且可选用1到3个碳原子的支链或线性烷氧基取代，Z从以下组中选择：--CH=CH--, --CHOH--CH=CH--, ##STR2## 和 --OCH.sub.2 --，X从以下组中选择：氢和甲基，Y从以下组中选择：1到5个碳原子的线性和支链烷氧基以及 ##STR3##，R'和R"是1到4个碳原子的线性或支链烷基，它们是杀虫剂，并且它们的制备方法。
• Prenyl transferase inhibitors
  申请人：Wayne State University

  公开号：US06586461B1

  公开（公告）日：2003-07-01

  Farnesyl diphosphate analogs, specifically the 3-substituted alcohol precursors of the diphosphate analogs, 3-allylfarnesol and 3-vinylfarnesol, are potent inhibitors of mammalian protein fanesyltransferase (FTase). 3-allylgeranylgeraniol is a highly specific cellular inhibitor of protein geranylgeranylation (GGTase I). Furthermore, these compounds are able to efficiently block the anchorage-dependent growth of ras transformed cells. While 3-allylfarnesol inhibits protein farnesylation in situ, 3-vinylfarnesol instead leads to the abnormal prenylation of proteins with the 3-vinylfarnesyl group. In a similar manner, treatment with 3-allylgeranylgeraniol inhibits protein geranylgeranylation while 3-vinylgeranylgeraniol restores protein geranylgeranylation in cells.

  法尼醇二磷酸盐类似物，特别是3-取代醇前体的二磷酸盐类似物，3-烯丙基法尼醇和3-乙烯基法尼醇，是哺乳动物蛋白质法尼基转移酶（FTase）的有效抑制剂。3-烯丙基戊二醇是蛋白质戊二烯基化（GGTase I）的高度特异性细胞抑制剂。此外，这些化合物能够有效地阻止ras转化细胞的附着依赖性生长。虽然3-烯丙基法尼醇在原位抑制蛋白质法尼基化，但3-乙烯基法尼醇则会导致蛋白质以3-乙烯基法尼基团异常戊二烯基化。类似地，使用3-烯丙基戊二醇处理可以抑制蛋白质戊二烯基化，而3-乙烯基戊二醇则可以恢复细胞中的蛋白质戊二烯基化。