diethyl (E)-1-ethoxy-3-hydroxy-5,9-dimethyl-1,8-decadien-2-ylphosphonate

• 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: diethyl (E)-1-ethoxy-3-hydroxy-5,9-dimethyl-1,8-decadien-2-ylphosphonate
• 英文别名: (1E)-2-diethoxyphosphoryl-1-ethoxy-5,9-dimethyldeca-1,8-dien-3-ol
• 化学式: C₁₈H₃₅O₅P
• 分子量: 362.447
• InChiKey: AYWWPZLQHOXXFG-NBVRZTHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl (E)-1-ethoxy-3-hydroxy-5,9-dimethyl-1,8-decadien-2-ylphosphonate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以58%的产率得到diethyl (4aS*,6S*,8aS*)-1,1,6-trimethyl-4a,5,6,7,8,8a-hexahydro-1H-2-benzopyran-4-ylphosphonate
  参考文献：
  名称：

  Synthesis and Synthetic Application of α-Formylvinylphosphonates. Facile Synthesis of Phosphono-Substituted Heterocyclic Compounds

  摘要：

  The beta-ethoxy-alpha-phosphonovinyl anion, generated from beta-(ethoxy)vinylphosphonate 1 and LDA, reacted with aldehydes and ketones or phenyl isocyanate to give the corresponding allylic alcohols 2a-m or 1,3-diphenyl-5-phosphonouracil 4 in good or moderate yields. Treatment of the alcohols 2a-d,g,h,j with trifluoroacetic acid led to alpha-formylvinylphosphonates 5a-d,g,h,j in excellent yields. Synthetic application of the alpha-formylvinylphosphonates 5a-d,g,h to phosphono-substituted heterocyclic compounds was studied.

  DOI：

  10.1021/jo000149t
• 作为产物：
  描述：

  香茅醛 、 (E)-Diethyl 2-ethoxyethenylphosphonate 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.1h， 以79%的产率得到diethyl (E)-1-ethoxy-3-hydroxy-5,9-dimethyl-1,8-decadien-2-ylphosphonate
  参考文献：
  名称：

  Synthesis and Synthetic Application of α-Formylvinylphosphonates. Facile Synthesis of Phosphono-Substituted Heterocyclic Compounds

  摘要：

  The beta-ethoxy-alpha-phosphonovinyl anion, generated from beta-(ethoxy)vinylphosphonate 1 and LDA, reacted with aldehydes and ketones or phenyl isocyanate to give the corresponding allylic alcohols 2a-m or 1,3-diphenyl-5-phosphonouracil 4 in good or moderate yields. Treatment of the alcohols 2a-d,g,h,j with trifluoroacetic acid led to alpha-formylvinylphosphonates 5a-d,g,h,j in excellent yields. Synthetic application of the alpha-formylvinylphosphonates 5a-d,g,h to phosphono-substituted heterocyclic compounds was studied.

  DOI：

  10.1021/jo000149t

文献信息

• Synthesis and Synthetic Application of α-Formylvinylphosphonates. Facile Synthesis of Phosphono-Substituted Heterocyclic Compounds
  作者：Ryoji Kouno、Terunobu Tsubota、Tatsuo Okauchi、Toru Minami

  DOI：10.1021/jo000149t

  日期：2000.7.1

  The beta-ethoxy-alpha-phosphonovinyl anion, generated from beta-(ethoxy)vinylphosphonate 1 and LDA, reacted with aldehydes and ketones or phenyl isocyanate to give the corresponding allylic alcohols 2a-m or 1,3-diphenyl-5-phosphonouracil 4 in good or moderate yields. Treatment of the alcohols 2a-d,g,h,j with trifluoroacetic acid led to alpha-formylvinylphosphonates 5a-d,g,h,j in excellent yields. Synthetic application of the alpha-formylvinylphosphonates 5a-d,g,h to phosphono-substituted heterocyclic compounds was studied.