(2Z,8E,10E)-1-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-dodeca-2,8,10-trien-4-ol | 192774-53-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2Z,8E,10E)-1-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-dodeca-2,8,10-trien-4-ol
• 英文别名: (2Z,8E,10E)-1-[tert-butyl(dimethyl)silyl]oxy-6-methyldodeca-2,8,10-trien-4-ol
• CAS: 192774-53-1
• 化学式: C₁₉H₃₆O₂Si
• 分子量: 324.579
• InChiKey: YCJTVCUCXCSFOY-UGQUYLDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.47
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2Z,8E,10E)-1-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-dodeca-2,8,10-trien-4-ol 在 草酰氯 、 sodium methylate 、 二氯乙基铝 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (3S,4aS,7R,8R,8aR)-8-(tert-Butyl-dimethyl-silanyloxymethyl)-3,7-dimethyl-3,4,4a,7,8,8a-hexahydro-2H-naphthalen-1-one
  参考文献：
  名称：

  Enantioselective Total Synthesis of (+)-6-epi-Mevinolin and Its Analogs. Efficient Construction of the Hexahydronaphthalene Moiety by High Pressure-Promoted Intramolecular Diels−Alder Reaction of (R,2Z,8E,10E)-1-[(tert-Butyldimethylsilyl)oxy]-6-methyl-2,8,10-dodecatrien-4-one

  摘要：

  3-Hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase inhibitors, (+)-6-epi-mevinolin (2a) and (+)-6-epi-4a,5-dihydromevinolin (2b), were prepared by combining two nonracemic units, phosphonate 3 and decalin 4, which were prepared from enantiopure 3-substituted pentanedioic acid monoesters 5a and 5b, respectively. Each acid was synthesized from cyclic anhydrides 7a and 7b by diastereoselective ring opening by means of (S)-benzyl mandelate as a common chiral auxiliary. The construction of decalin moiety 4 was accomplished by asymmetric intramolecular Diels-Alder (IMDA) reaction of nonracemic trienone 6 bearing a methyl group as a chiral controller. The IMDA diastereoselectivity of trienone 6 is discussed in terms of the configuration of(E)- and (Z)-dienophiles which are activated by an endogenous carbonyl group. The IMDA reaction of(R)-(Z)-6 under high pressure is highly selective and gives cis-decalins exclusively with preferential formation of 4 over 16. The inhibitory activity of (+)-6-epi-mevinolin (2a) and several analogs against HMG-CoA reductase was compared with mevinolin (1b). (+)-6-epi-Mevinolin (2a) was shown to be half as potent as mevinolin (1b) while (+)-6-epi-4a,5-dihydromevinolin (2b) was as potent as mevinolin.

  DOI：

  10.1021/jo970444m
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 咪唑 、 正丁基锂 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 (2Z,8E,10E)-1-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-dodeca-2,8,10-trien-4-ol
  参考文献：
  名称：

  Enantioselective Total Synthesis of (+)-6-epi-Mevinolin and Its Analogs. Efficient Construction of the Hexahydronaphthalene Moiety by High Pressure-Promoted Intramolecular Diels−Alder Reaction of (R,2Z,8E,10E)-1-[(tert-Butyldimethylsilyl)oxy]-6-methyl-2,8,10-dodecatrien-4-one

  摘要：

  3-Hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase inhibitors, (+)-6-epi-mevinolin (2a) and (+)-6-epi-4a,5-dihydromevinolin (2b), were prepared by combining two nonracemic units, phosphonate 3 and decalin 4, which were prepared from enantiopure 3-substituted pentanedioic acid monoesters 5a and 5b, respectively. Each acid was synthesized from cyclic anhydrides 7a and 7b by diastereoselective ring opening by means of (S)-benzyl mandelate as a common chiral auxiliary. The construction of decalin moiety 4 was accomplished by asymmetric intramolecular Diels-Alder (IMDA) reaction of nonracemic trienone 6 bearing a methyl group as a chiral controller. The IMDA diastereoselectivity of trienone 6 is discussed in terms of the configuration of(E)- and (Z)-dienophiles which are activated by an endogenous carbonyl group. The IMDA reaction of(R)-(Z)-6 under high pressure is highly selective and gives cis-decalins exclusively with preferential formation of 4 over 16. The inhibitory activity of (+)-6-epi-mevinolin (2a) and several analogs against HMG-CoA reductase was compared with mevinolin (1b). (+)-6-epi-Mevinolin (2a) was shown to be half as potent as mevinolin (1b) while (+)-6-epi-4a,5-dihydromevinolin (2b) was as potent as mevinolin.

  DOI：

  10.1021/jo970444m