Carbamic acid 1-((E)-2,3-diiodo-propenyl)-octyl ester | 134881-19-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: Carbamic acid 1-((E)-2,3-diiodo-propenyl)-octyl ester
• 英文别名: [(E)-1,2-diiodoundec-2-en-4-yl] carbamate
• CAS: 134881-19-9
• 化学式: C₁₂H₂₁I₂NO₂
• 分子量: 465.113
• InChiKey: UVTADKPXNZHIQD-CSKARUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.56
• 重原子数：
  17.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  52.32
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  在 碘 、 碳酸氢钠 、 potassium carbonate 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 反应 3.5h， 生成 Carbamic acid 1-((E)-2,3-diiodo-propenyl)-octyl ester
  参考文献：
  名称：

  Iodocyclization of the (tolylsulfonyl)- and (trichloroacetyl)carbamates of secondary .alpha.-allenic alcohols. Highly diastereoselective synthesis of syn-1,2-amino alcohols and trans-5-alkyl-1-oxo-2-oxazolidine-4-carboxylic acids

  摘要：

  The iodocyclization of tosyl- and (trichloroacetyl)carbamates 9 and 10, respectively, of secondary alpha-allenic alcohols is described. The cyclofunctionalization reactions are highly diastereoselective, providing trans-5-alkyl-4-(1-iodoethylene)-2-oxazolidinones 11 and 12 as the major diastereomers in ratios of 6.3:1 to > 99: < 1. The mechanism of cyclization involves the initial formation of diiodides resulting from the addition of I2 to the terminal olefin of the allene moiety, followed by a kinetically controlled intramolecular SN2' displacement of iodide. Hydrolysis and acetylation of the N-tosyloxazolidinones 11 provide syn-1,2-amino alcohol derivatives 15. Alternatively, ozonolysis of the vinyl iodides derived from the cyclization of the (trichloroacetyl)carbamates 12 provides a novel, efficient, and highly diastereoselective route to trans-5-alkyl-2-oxazolidinone-4-carboxylic acids 25 and esters 26.

  DOI：

  10.1021/jo00016a016