<1S-<1α,3α,7β,8β(2S^*,4S^*)8aβ>>-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-<2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl>-1-naphthalenyl benzeneacetate | 79902-50-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: <1S-<1α,3α,7β,8β(2S^*,4S^*)8aβ>>-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-<2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl>-1-naphthalenyl benzeneacetate
• 英文别名: [1S-(1α,3α,7β,8β(2S^*,4S^*)8aβ)]-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1-naphthalenyl benzeneacetate；Phenyl-acetic acid 8-[2-(4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester；[(1S,3R,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] 2-phenylacetate
• CAS: 79902-50-4
• 化学式: C₂₇H₃₄O₅
• 分子量: 438.564
• InChiKey: QXEJOEBXRQAVIM-KQGSDPMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-(叔丁基二甲基甲硅烷氧基)-6-[2-(8-羟基-2,6-二甲基-1,2,6,7,8,8a-六氢萘)-乙基]-四氢吡喃-2-酮 在 四丁基氟化铵 、 4-吡咯烷基吡啶 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 93.0h， 生成 <1S-<1α,3α,7β,8β(2S^*,4S^*)8aβ>>-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-<2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl>-1-naphthalenyl benzeneacetate
  参考文献：
  名称：

  3-Hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors. 4. Side-chain ester derivatives of mevinolin

  摘要：

  Modification of the 2(S)-methylbutyryl moiety of mevinolin led to a series of side chain ester derivatives. A systematic exploration of the structure-activity relationships showed that the introduction of an additional aliphatic group on the carbon alpha to the carbonyl group increased potency. This observation led to the synthesis of compound 16, which has about 2.5 times the intrinsic inhibitory activity of mevinolin.

  DOI：

  10.1021/jm00155a040