(3aR,7aR)-2-butan-2-yloxy-1,3-dimethyl-3a,4,5,6,7,7a-hexahydrobenzo[d][1,3,2]diazaphosphole 2-oxide | 137943-83-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: (3aR,7aR)-2-butan-2-yloxy-1,3-dimethyl-3a,4,5,6,7,7a-hexahydrobenzo[d][1,3,2]diazaphosphole 2-oxide
• CAS: 137943-83-0；138051-25-9
• 化学式: C₁₂H₂₅N₂O₂P
• 分子量: 260.316
• InChiKey: RKLWORVWNBZOMH-PQDIPPBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.78
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  1,4,5,6-四氯-3,3-二羟基-7-(2,4-二氯苯基)-二环[2.2.2]辛-5,7-二烯-2-酮 在 lithium aluminium tetrahydride 、 sodium hydride 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 42.5h， 生成 (3aR,7aR)-2-butan-2-yloxy-1,3-dimethyl-3a,4,5,6,7,7a-hexahydrobenzo[d][1,3,2]diazaphosphole 2-oxide
  参考文献：
  名称：

  A new reagent for the determination of the optical purity of primary, secondary, and tertiary chiral alcohols and of thiols

  摘要：

  A new reagent is described for the determination of the enantiomeric excess of chiral alcohols. This derivatizing agent (22) is a diazaphospholidine, easily prepared from hexamethylphosphorous triamide (HMPT) and a chiral diamine having a C2 axis of symmetry: (R,R)-N,N'-dimethylcyclohexane-1,2-diamine. A large array of primary, secondary, and tertiary alcohols, functionalized or not, as well as thiols were successfully tested. The derivatization is fast at room temperature, proceeds without kinetic discrimination, does not need any added cosolvent or coreagent, and may be run directly in an NMR tube. This new reagent allows an accurate analysis by P-31 NMR spectroscopy, and after conversion of the trivalent phosphorus derivative to the corresponding P-sulfide in the NMR tube, a new P-31 NMR spectrum may be recorded. In addition, most of the P-sulfide derivatives when submitted to GC or HPLC analyses exhibit base line separation.

  DOI：

  10.1021/jo00030a034

文献信息

• A new reagent for a very simple and efficient determination of enantiomeric purity of alcohols by 31P NMR
  作者：Alexandre Alexakis、Stephane Mutti、Jean F. Normant、Pierre Mangeney

  DOI：10.1016/s0957-4166(00)86347-8

  日期：1990.1

  A new reagent is described for the determination of enantiomeric excess of chiral alcohols. This derivatizing agent allows an accurate analysis by 31P NMR. A large array of primary, secondary, and tertiary alcohols, functionalized or not, were successfully tested. Reagent 7 is easy to prepare and reacts alone with the chiral alcohol, at room temperature, eventually directly in the NMR tube.

  描述了一种用于测定手性醇对映体过量的新试剂。该衍生剂可以通过31 P NMR进行准确的分析。成功地测试了各种伯醇，仲醇和叔醇，无论它们是否官能化。试剂7易于制备，可与手性醇在室温下单独反应，最终直接在NMR管中进行反应。