trans-5-cyclohexyl-2-oxooxazolidine-4-carboxylic acid | 134881-22-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: trans-5-cyclohexyl-2-oxooxazolidine-4-carboxylic acid
• 英文别名: (4S,5R)-5-cyclohexyl-2-oxo-1,3-oxazolidine-4-carboxylic acid
• CAS: 134881-22-4
• 化学式: C₁₀H₁₅NO₄
• 分子量: 213.233
• InChiKey: CLRAEBBDRPIBHM-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  trans-5-cyclohexyl-2-oxooxazolidine-4-carboxylic acid 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 8.0h， 以83%的产率得到(2RS,3SR)-2-amino-3-cyclohexyl-3-hydroxy-propionic acid
  参考文献：
  名称：

  Pd-Catalyzed Intramolecular Aminohydroxylation of Alkenes with Hydrogen Peroxide as Oxidant and Water as Nucleophile

  摘要：

  A palladium-catalyzed intramolecular aminohydroxylation of alkenes was developed, in which H2O2 was applied as the sole oxidant. A variety of related alkyl alcohols could be successfully obtained with good yields and excellent diastereoselectivities, which directly derived from oxidation cleavage of alkyl C-Pd bond by H2O2. Facile transformation of these products provided a powerful tool toward the synthesis of 2-amino-1,3-diols and 3-ol amino acids. Preliminary mechanistic studies revealed that major nucleophilic attack of water (S(N)2 type) at high-valent Pd center contributes to the final C-O(H) bond formation.

  DOI：

  10.1021/ja412023b
• 作为产物：
  描述：

  trans-4-(1-iodoethylene)-5-cyclohexyl-2-oxazolidinone 在 氢氧化钾 、 臭氧 作用下， 生成 trans-5-cyclohexyl-2-oxooxazolidine-4-carboxylic acid
  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