(3aR,7aR)-1,3-dimethyl-2-[(2S)-octan-2-yl]oxy-3a,4,5,6,7,7a-hexahydrobenzo[d][1,3,2]diazaphosphole | 131897-19-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丁烷
• 英文名称: (3aR,7aR)-1,3-dimethyl-2-[(2S)-octan-2-yl]oxy-3a,4,5,6,7,7a-hexahydrobenzo[d][1,3,2]diazaphosphole
• CAS: 131897-19-3
• 化学式: C₁₆H₃₃N₂OP
• 分子量: 300.425
• InChiKey: XRYFCGNRNBEVQR-ARFHVFGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.78
• 重原子数：
  20.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  15.71
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (3aR,7aR)-1,3-dimethyl-2-[(2S)-octan-2-yl]oxy-3a,4,5,6,7,7a-hexahydrobenzo[d][1,3,2]diazaphosphole 在 sulfur 作用下， 生成 (3aR,7aR)-1,3-dimethyl-2-[(2S)-octan-2-yl]oxy-2-sulfanylidene-3a,4,5,6,7,7a-hexahydrobenzo[d][1,3,2]diazaphosphole
  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
• 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 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 132.0h， 生成 (3aR,7aR)-1,3-dimethyl-2-[(2S)-octan-2-yl]oxy-3a,4,5,6,7,7a-hexahydrobenzo[d][1,3,2]diazaphosphole
  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