(Z)-2-[Hydroxy-(2-methyl-[1,3]dithian-2-yl)-methyl]-tetradeca-2,13-dienoic acid ethyl ester | 637756-05-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (Z)-2-[Hydroxy-(2-methyl-[1,3]dithian-2-yl)-methyl]-tetradeca-2,13-dienoic acid ethyl ester
• 英文别名: ethyl (2Z)-2-[hydroxy-(2-methyl-1,3-dithian-2-yl)methyl]tetradeca-2,13-dienoate
• CAS: 637756-05-9
• 化学式: C₂₂H₃₈O₃S₂
• 分子量: 414.674
• InChiKey: FOFPHAPQLLRDNB-MNDPQUGUSA-N

物化性质

• 沸点：
  525.9±45.0 °C(predicted)
• 密度：
  1.045±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  27
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  97.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-2-[Hydroxy-(2-methyl-[1,3]dithian-2-yl)-methyl]-tetradeca-2,13-dienoic acid ethyl ester 在 N-氯代丁二酰亚胺 、 silver nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.08h， 以82%的产率得到ethyl (2Z)-2-(1-hydroxy-2-oxopropyl)-tetradeca-2,13-dienoate
  参考文献：
  名称：

  Vinylalumination for the Synthesis of Functionalized Allyl Alcohols, Vinylepoxides, and α-Alkylidene-β-hydroxy-γ-lactones

  摘要：

  A modified hydroalumination protocol for the preparation of [alpha-(ethoxycarbonyl)vinyl]diisobutyl-aluminum and its beta-methyl or -phenyl analogues was developed. These vinylaluminum reagents react with aldehydes and ketones to provide the corresponding functionalized allyl alcohols in good to excellent yields. Perfluoroalkyl and -aryl carbonyl compounds, alpha-keto esters, alpha-acyl cyanides, and alpha-acetylenic ketones provide the corresponding alpha-hydroxyalkenes in high yields. The allyl alcohol product ratios from the vinylalumination of unsymmetrical alpha-diketones with [alpha-(ethoxycarbonyl)vinyl] diisobutylaluminum and its beta-methyl or -phenyl analogues depend on the steric and electronic environments of the ketones as well as the reagents. The products from the vinylalumination of alpha-bromoaldehydes and -ketones were cyclized With K2CO3 or KF under nonaqueous conditions to provide functionalized vinylepoxides in high yields. Vinylaluminations of keto-protected pyruvaldehyde provided the products, which were converted to alpha-alkylidene-beta-hydroxy-gamma-lactones.

  DOI：

  10.1021/jo034954u
• 作为产物：
  描述：

  2-甲基-1,3-二噻烷 在 正丁基锂 、 二异丁基氢化铝 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 15.5h， 生成 (Z)-2-[Hydroxy-(2-methyl-[1,3]dithian-2-yl)-methyl]-tetradeca-2,13-dienoic acid ethyl ester
  参考文献：
  名称：

  Vinylalumination for the Synthesis of Functionalized Allyl Alcohols, Vinylepoxides, and α-Alkylidene-β-hydroxy-γ-lactones

  摘要：

  A modified hydroalumination protocol for the preparation of [alpha-(ethoxycarbonyl)vinyl]diisobutyl-aluminum and its beta-methyl or -phenyl analogues was developed. These vinylaluminum reagents react with aldehydes and ketones to provide the corresponding functionalized allyl alcohols in good to excellent yields. Perfluoroalkyl and -aryl carbonyl compounds, alpha-keto esters, alpha-acyl cyanides, and alpha-acetylenic ketones provide the corresponding alpha-hydroxyalkenes in high yields. The allyl alcohol product ratios from the vinylalumination of unsymmetrical alpha-diketones with [alpha-(ethoxycarbonyl)vinyl] diisobutylaluminum and its beta-methyl or -phenyl analogues depend on the steric and electronic environments of the ketones as well as the reagents. The products from the vinylalumination of alpha-bromoaldehydes and -ketones were cyclized With K2CO3 or KF under nonaqueous conditions to provide functionalized vinylepoxides in high yields. Vinylaluminations of keto-protected pyruvaldehyde provided the products, which were converted to alpha-alkylidene-beta-hydroxy-gamma-lactones.

  DOI：

  10.1021/jo034954u

文献信息

• Vinylalumination for the Synthesis of Functionalized Allyl Alcohols, Vinylepoxides, and α-Alkylidene-β-hydroxy-γ-lactones
  作者：P. Veeraraghavan Ramachandran、Michael T. Rudd、Thomas E. Burghardt、M. Venkat Ram Reddy

  DOI：10.1021/jo034954u

  日期：2003.11.1

  A modified hydroalumination protocol for the preparation of [alpha-(ethoxycarbonyl)vinyl]diisobutyl-aluminum and its beta-methyl or -phenyl analogues was developed. These vinylaluminum reagents react with aldehydes and ketones to provide the corresponding functionalized allyl alcohols in good to excellent yields. Perfluoroalkyl and -aryl carbonyl compounds, alpha-keto esters, alpha-acyl cyanides, and alpha-acetylenic ketones provide the corresponding alpha-hydroxyalkenes in high yields. The allyl alcohol product ratios from the vinylalumination of unsymmetrical alpha-diketones with [alpha-(ethoxycarbonyl)vinyl] diisobutylaluminum and its beta-methyl or -phenyl analogues depend on the steric and electronic environments of the ketones as well as the reagents. The products from the vinylalumination of alpha-bromoaldehydes and -ketones were cyclized With K2CO3 or KF under nonaqueous conditions to provide functionalized vinylepoxides in high yields. Vinylaluminations of keto-protected pyruvaldehyde provided the products, which were converted to alpha-alkylidene-beta-hydroxy-gamma-lactones.