Tert-butyl bis(2-cyanoethyl) phosphite | 217939-46-3

• 分子结构分类: 有机化合物 - 有机磷化合物 - 亚磷酸三烷基酯
• 英文名称: Tert-butyl bis(2-cyanoethyl) phosphite
• CAS: 217939-46-3
• 化学式: C₁₀H₁₇N₂O₃P
• 分子量: 244.23
• InChiKey: OWDCFOHPHKGRDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  75.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Tert-butyl bis(2-cyanoethyl) phosphite 在 碘 作用下， 生成 tetra-(2-cyanoethyl)pyrophosphate
  参考文献：
  名称：

  Phosphoramidites derived from tertiary alcohols. Why do they sometimes couple with low efficiency?

  摘要：

  tert-Alkyl phosphoramidites are somewhat sterically hindered, but give phosphites in good yields with tetrazole catalysis when the coupling time with alcohols is prolonged. Low yields of phosphotriesters are caused by elimination of the tertiary alkyl group during the subsequent oxidation of the phosphite with iodine/water/pyridine, and can be avoided by the use of tert-butyl hydroperoxide as the oxidant. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01844-9
• 作为产物：
  描述：

  3-羟基丙腈 、 O-tert-butyl-O'-β-cyanoethyl-N,N-diisopropylphosphoramidite 在 四氮唑 作用下， 以 乙腈 为溶剂， 反应 0.03h， 生成 Tert-butyl bis(2-cyanoethyl) phosphite
  参考文献：
  名称：

  Phosphoramidites derived from tertiary alcohols. Why do they sometimes couple with low efficiency?

  摘要：

  tert-Alkyl phosphoramidites are somewhat sterically hindered, but give phosphites in good yields with tetrazole catalysis when the coupling time with alcohols is prolonged. Low yields of phosphotriesters are caused by elimination of the tertiary alkyl group during the subsequent oxidation of the phosphite with iodine/water/pyridine, and can be avoided by the use of tert-butyl hydroperoxide as the oxidant. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01844-9

文献信息

• Phosphoramidites derived from tertiary alcohols. Why do they sometimes couple with low efficiency?
  作者：Claus Scheuer-Larsen、Britta M. Dahl、Jesper Wengel、Otto Dahl

  DOI：10.1016/s0040-4039(98)01844-9

  日期：1998.11

  tert-Alkyl phosphoramidites are somewhat sterically hindered, but give phosphites in good yields with tetrazole catalysis when the coupling time with alcohols is prolonged. Low yields of phosphotriesters are caused by elimination of the tertiary alkyl group during the subsequent oxidation of the phosphite with iodine/water/pyridine, and can be avoided by the use of tert-butyl hydroperoxide as the oxidant. (C) 1998 Elsevier Science Ltd. All rights reserved.