| 131141-48-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 131141-48-5
• 化学式: C₁₆H₂₁NO₄S
• 分子量: 323.413
• InChiKey: MYZUXMNNKMEAIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  84.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  在 碘 作用下， 生成
  参考文献：
  名称：

  A highly stereoselective conversion of α-allenic alcohols to syn-1,2-diol derivatives

  摘要：

  Alpha-Allenic alcohols 4 are converted with high diastereoselectivity via an iodocyclization process into the syn-1,2-diol derivatives 10.

  DOI：

  10.1016/s0040-4039(00)91949-x
• 作为产物：
  描述：

  异戊醛 生成
  参考文献：
  名称：

  A highly stereoselective conversion of α-allenic alcohols to 1,2-syn amino alcohol derivatives via iodocarbamation

  摘要：

  DOI：

  10.1016/s0040-4039(00)97592-0

文献信息

• 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
  作者：Richard W. Friesen、Aleksandra E. Kolaczewska

  DOI：10.1021/jo00016a016

  日期：1991.8

  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.
• FRIESEN, RICHARD W., TETRAHEDRON LETT., 31,(1990) N0, C. 4249-4250
  作者：FRIESEN, RICHARD W.

  DOI：——

  日期：——