(1'S,6S)-6-{2'-{[dimethyl(1,1,2-trimethylpropyl)silyl]oxy}-1'-methylethyl}-3-methylcyclohex-2-en-1-one | 252289-24-0

• 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: (1'S,6S)-6-{2'-{[dimethyl(1,1,2-trimethylpropyl)silyl]oxy}-1'-methylethyl}-3-methylcyclohex-2-en-1-one
• 英文别名: (6S)-6-[(2S)-1-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxypropan-2-yl]-3-methylcyclohex-2-en-1-one
• CAS: 252289-24-0
• 化学式: C₁₈H₃₄O₂Si
• 分子量: 310.552
• InChiKey: XQEHJRFPSKWHKP-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.21
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  (1'S,6S)-6-{2'-{[dimethyl(1,1,2-trimethylpropyl)silyl]oxy}-1'-methylethyl}-3-methylcyclohex-2-en-1-one 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 、 sodium tetrahydroborate 、 cerium(III) chloride 、 lithium diethylamide 、 四丁基氟化铵 、 双氧水 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 47.0h， 生成 (1'R,2S)-2-(4'-methylenecyclohex-2'-en-1'-yl)propyl 4-nitrobenzenesulfonate
  参考文献：
  名称：

  Stereospecific Synthesis of (−)-β-Turmerone and (−)-Bisacurol

  摘要：

  The structure of (+)-beta-turmerone ((+)-1a), a constituent of the rhizomes of Curcuma longa LINN., and Curcuma xanthorriza, is established as (1'R,6S)-2-methyl-6-(4'-methylenecyclohex-2'-en-1'-yl)hept-2-en-4-one by synthesis of its enantiomer (-)-1a, and of the corresponding (1'S,6S)-diastereoisomer (+)-1b as well. In a stereospecific seventeen-step procedure, the monoterpene diols 2a and 2b of well-established configuration are convened into the target compounds (-)-1a and (+)-1b, respectively. Moreover, (-)-bisacurol (-)-3a(II), the enantiomer of another bisabolane sesquiterpene derived from Curcuma xanthorriza, is obtained as a single stereoisomer and shown to be (1'S,6R)-2-methyl-6-(4'-methylenecyclohex-2'-en-1'-yl)hept-2-en-4-ol, the relative configuration at the remaining OH-substituted chiral center C(4) still being unknown.

  DOI：

  10.1002/(sici)1522-2675(19991006)82:10<1610::aid-hlca1610>3.0.co;2-t
• 作为产物：
  描述：

  (1R,2S,5R)-2-[(S)-2-hydroxy-1-methylethyl]-5-methylcyclohexan-1-ol 在 咪唑 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 草酰氯 、 二甲基亚砜 、 三乙胺 、 二异丙胺 作用下， 以 四氢呋喃 、 2,4,6-三甲基吡啶 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 (1'S,6S)-6-{2'-{[dimethyl(1,1,2-trimethylpropyl)silyl]oxy}-1'-methylethyl}-3-methylcyclohex-2-en-1-one
  参考文献：
  名称：

  Stereospecific Synthesis of (−)-β-Turmerone and (−)-Bisacurol

  摘要：

  The structure of (+)-beta-turmerone ((+)-1a), a constituent of the rhizomes of Curcuma longa LINN., and Curcuma xanthorriza, is established as (1'R,6S)-2-methyl-6-(4'-methylenecyclohex-2'-en-1'-yl)hept-2-en-4-one by synthesis of its enantiomer (-)-1a, and of the corresponding (1'S,6S)-diastereoisomer (+)-1b as well. In a stereospecific seventeen-step procedure, the monoterpene diols 2a and 2b of well-established configuration are convened into the target compounds (-)-1a and (+)-1b, respectively. Moreover, (-)-bisacurol (-)-3a(II), the enantiomer of another bisabolane sesquiterpene derived from Curcuma xanthorriza, is obtained as a single stereoisomer and shown to be (1'S,6R)-2-methyl-6-(4'-methylenecyclohex-2'-en-1'-yl)hept-2-en-4-ol, the relative configuration at the remaining OH-substituted chiral center C(4) still being unknown.

  DOI：

  10.1002/(sici)1522-2675(19991006)82:10<1610::aid-hlca1610>3.0.co;2-t

文献信息

• Stereospecific Synthesis of (−)-β-Turmerone and (−)-Bisacurol
  作者：Wolfgang Kreiser、Ferdinand Körner

  DOI：10.1002/(sici)1522-2675(19991006)82:10<1610::aid-hlca1610>3.0.co;2-t

  日期：1999.10.6

  The structure of (+)-beta-turmerone ((+)-1a), a constituent of the rhizomes of Curcuma longa LINN., and Curcuma xanthorriza, is established as (1'R,6S)-2-methyl-6-(4'-methylenecyclohex-2'-en-1'-yl)hept-2-en-4-one by synthesis of its enantiomer (-)-1a, and of the corresponding (1'S,6S)-diastereoisomer (+)-1b as well. In a stereospecific seventeen-step procedure, the monoterpene diols 2a and 2b of well-established configuration are convened into the target compounds (-)-1a and (+)-1b, respectively. Moreover, (-)-bisacurol (-)-3a(II), the enantiomer of another bisabolane sesquiterpene derived from Curcuma xanthorriza, is obtained as a single stereoisomer and shown to be (1'S,6R)-2-methyl-6-(4'-methylenecyclohex-2'-en-1'-yl)hept-2-en-4-ol, the relative configuration at the remaining OH-substituted chiral center C(4) still being unknown.