Acetic acid (1S,2R)-2,3-diacetoxy-1-((1S,6S)-6-formyl-3,4-dimethyl-cyclohex-3-enyl)-propyl ester | 149117-05-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Acetic acid (1S,2R)-2,3-diacetoxy-1-((1S,6S)-6-formyl-3,4-dimethyl-cyclohex-3-enyl)-propyl ester
• 英文别名: [(2R,3S)-2,3-diacetyloxy-3-[(1S,6S)-6-formyl-3,4-dimethylcyclohex-3-en-1-yl]propyl] acetate
• CAS: 149117-05-5
• 化学式: C₁₈H₂₆O₇
• 分子量: 354.4
• InChiKey: OVILBFJWKJZTDP-XDNAFOTISA-N

物化性质

• 沸点：
  411.0±45.0 °C(predicted)
• 密度：
  1.164±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  96
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Acetic acid (1S,2R)-2,3-diacetoxy-1-((1S,6S)-6-formyl-3,4-dimethyl-cyclohex-3-enyl)-propyl ester 在 盐酸 、 sodium tetrahydroborate 作用下， 生成 Acetic acid (R)-2-acetoxy-1-((1S,2S,4S,5R,7S)-2-acetoxymethyl-4,5-dimethyl-6-oxa-bicyclo[3.2.1]oct-7-yl)-ethyl ester
  参考文献：
  名称：

  Diels-Alder reactions with an α,β-unsaturated aldehydo-sugar. A route to 6-oxabicyclo[3.2.1]octanes

  摘要：

  Thermal and catalytic Diels-Alder reactions of 1 with 2,3-dimethyl-1,3-butadiene gave 4-formyl-5-glycocyclohexenes 2 and 3. Absolute configurations at the new chiral centers in the addutcs are based on polarimetric correlation with known compounds. On reduction and acid treatment, the adducts 2 and 3 were converted into 6-oxabicyclo[3.2.1]octanes 13 and 15.

  DOI：

  10.1016/s0040-4039(00)60786-4
• 作为产物：
  描述：

  (2E)-4,5,6-tri-O-acetyl-2,3-dideoxy-aldehydo-D-erythro-hex-2-enose 、 2,3-二甲基-1,3-丁二烯 在 三氯化铝 作用下， 以 甲苯 为溶剂， 反应 96.0h， 生成 Acetic acid (1S,2R)-2,3-diacetoxy-1-((1R,6R)-6-formyl-3,4-dimethyl-cyclohex-3-enyl)-propyl ester 、 Acetic acid (1S,2R)-2,3-diacetoxy-1-((1S,6S)-6-formyl-3,4-dimethyl-cyclohex-3-enyl)-propyl ester
  参考文献：
  名称：

  Diels-Alder reactions with an α,β-unsaturated aldehydo-sugar. A route to 6-oxabicyclo[3.2.1]octanes

  摘要：

  Thermal and catalytic Diels-Alder reactions of 1 with 2,3-dimethyl-1,3-butadiene gave 4-formyl-5-glycocyclohexenes 2 and 3. Absolute configurations at the new chiral centers in the addutcs are based on polarimetric correlation with known compounds. On reduction and acid treatment, the adducts 2 and 3 were converted into 6-oxabicyclo[3.2.1]octanes 13 and 15.

  DOI：

  10.1016/s0040-4039(00)60786-4