(S)-4-((S)-2-Methoxy-pent-4-ynyl)-2,2-dimethyl-[1,3]dioxolane | 290343-10-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-4-((S)-2-Methoxy-pent-4-ynyl)-2,2-dimethyl-[1,3]dioxolane
• CAS: 290343-10-1
• 化学式: C₁₁H₁₈O₃
• 分子量: 198.262
• InChiKey: ODBZAWOLERPGLD-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.57
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-4-((S)-2-Methoxy-pent-4-ynyl)-2,2-dimethyl-[1,3]dioxolane 在 双(乙腈)氯化钯(II) 4-甲基苯磺酸吡啶 、 对苯醌 作用下， 以 甲醇 为溶剂， 生成 methyl 2-[(1S,3R,5S)-3-methoxy-6,8-dioxabicyclo[3.2.1]octan-5-yl]acetate
  参考文献：
  名称：

  Stereoselective synthesis of substituted ketopyranose subunits of polyketide natural products by intramolecular alkoxycarbonylation of δ-alkynyl alcohols

  摘要：

  Upon treatment with 5 mol% Pd(MeCN)(2)Cl-2 in methanol containing 1.1-1.5 equiv. of p-benzoquinone under 1 atm of CO, delta-hydroxy alkynes are converted to methyl ketopyranosides with excellent stereoselectivity. The reaction proceeds by sequential intramolecular alkoxypalladation of the alkyne followed by CO insertion and methanolysis, then an ensuing Pd+2-catalyzed 1,4-addition of methanol to the intermediate conjugated ester. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00705-x
• 作为产物：
  描述：

  (4S)-2,2-二甲基-1,3-二氧戊环-4-乙醛 在 15-冠醚-5 、 sodium hydride 作用下， 生成 (S)-4-((S)-2-Methoxy-pent-4-ynyl)-2,2-dimethyl-[1,3]dioxolane
  参考文献：
  名称：

  Stereoselective synthesis of substituted ketopyranose subunits of polyketide natural products by intramolecular alkoxycarbonylation of δ-alkynyl alcohols

  摘要：

  Upon treatment with 5 mol% Pd(MeCN)(2)Cl-2 in methanol containing 1.1-1.5 equiv. of p-benzoquinone under 1 atm of CO, delta-hydroxy alkynes are converted to methyl ketopyranosides with excellent stereoselectivity. The reaction proceeds by sequential intramolecular alkoxypalladation of the alkyne followed by CO insertion and methanolysis, then an ensuing Pd+2-catalyzed 1,4-addition of methanol to the intermediate conjugated ester. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00705-x