2-[(R)-(1S,2R,3S,4R)-3-(2,2-Dimethyl-propoxy)-4,7,7-trimethyl-bicyclo[2.2.1]heptane-2-sulfinyl]-acrylic acid methyl ester | 174321-83-6

• 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: 2-[(R)-(1S,2R,3S,4R)-3-(2,2-Dimethyl-propoxy)-4,7,7-trimethyl-bicyclo[2.2.1]heptane-2-sulfinyl]-acrylic acid methyl ester
• CAS: 174321-83-6
• 化学式: C₁₉H₃₂O₄S
• 分子量: 356.527
• InChiKey: UEGAWCFSSSWXJO-TWFBQZAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.68
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  环戊二烯 、 2-[(R)-(1S,2R,3S,4R)-3-(2,2-Dimethyl-propoxy)-4,7,7-trimethyl-bicyclo[2.2.1]heptane-2-sulfinyl]-acrylic acid methyl ester 以 二氯甲烷 为溶剂， 生成 (1S,2S,4S)-2-[(R)-(1S,2R,3S,4R)-3-(2,2-Dimethyl-propoxy)-4,7,7-trimethyl-bicyclo[2.2.1]heptane-2-sulfinyl]-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester 、 (1R,2S,4R)-2-[(R)-(1S,2R,3S,4R)-3-(2,2-Dimethyl-propoxy)-4,7,7-trimethyl-bicyclo[2.2.1]heptane-2-sulfinyl]-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Asymmetric Diels-Alder reaction of α-sulfinylacrylate derived from (1R, 2S, 3R)-3-mercaptocamphan-2-ol

  摘要：

  The Diels-Alder reaction of cyclopentadiene with a new chiral alpha-sulfinylacrylate, which was prepared from MerCO[(1R, 2S, 3R)-3-mercaptocamphan-2-ol] at -78 degrees C in the presence of ZnCl2 produced an endo-cycloadduct with 99.4% d.e. in 84% yield.

  DOI：

  10.1016/0957-4166(95)00420-3
• 作为产物：
  描述：

  2-[(1S,2R,3S,4R)-3-(2,2-Dimethyl-propoxy)-4,7,7-trimethyl-bicyclo[2.2.1]hept-2-ylsulfanyl]-propionic acid methyl ester 在 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 2-[(R)-(1S,2R,3S,4R)-3-(2,2-Dimethyl-propoxy)-4,7,7-trimethyl-bicyclo[2.2.1]heptane-2-sulfinyl]-acrylic acid methyl ester
  参考文献：
  名称：

  Asymmetric Diels-Alder reaction of α-sulfinylacrylate derived from (1R, 2S, 3R)-3-mercaptocamphan-2-ol

  摘要：

  The Diels-Alder reaction of cyclopentadiene with a new chiral alpha-sulfinylacrylate, which was prepared from MerCO[(1R, 2S, 3R)-3-mercaptocamphan-2-ol] at -78 degrees C in the presence of ZnCl2 produced an endo-cycloadduct with 99.4% d.e. in 84% yield.

  DOI：

  10.1016/0957-4166(95)00420-3