| 185805-22-5

• 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
• CAS: 185805-22-5
• 化学式: C₃₀H₃₀N₂O₆Si
• 分子量: 542.663
• InChiKey: GLYCTPNTXFGKJD-XDZXDJIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.63
• 重原子数：
  39.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  85.38
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  在 盐酸 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 methyl (1R,5S,6R)-3-[(1R)-2-(methoxymethoxy)-1-phenylethyl]-8-methyl-2,4-dioxo-3,8-diazabicyclo[3.2.1]octane-6-carboxylate
  参考文献：
  名称：

  Use of Silicon-Based Tethers to Control Diastereofacial Selectivity in Azomethine Ylide Cycloadditions¹

  摘要：

  A novel approach to controlling the diastereofacial selectivity of intramolecular dipolar cycloadditions of azomethine ylides (cf. 9 --> 8) by varying the structure a silicon-based tether is described. A correlation is found between the length of the tether dipolarophile conjugate (TDC) and the observed sense of diastereocontrol. Azomethine ylides incorporating longer [OSiPh(2)OCH(2)CH(2)OCOCH=CH2], [OSi(i-Pr)(2)OSi(i-Pr)(2)OCH2CH=CH2], and [OSiPh(2)OCH(2)CH=CH2] TDCs favor endo-si attack (14 --> 16, 19 --> 20, and 21 --> 22) while the shorter TDC [OSiR(2)CH(2)CH=CH2] leads to a reversal in selectivity favoring the endo-re product (23a,b --> 24a,b). Structures of the cycloadducts have been assigned on the basis of selected X-ray diffraction data in combination with chemical/spectral correlation experiments. The work described herein represents a conceptually new approach to stereocontrol and extends the use of silicon-based tethers in asymmetric synthesis.

  DOI：

  10.1021/jo9609034
• 作为产物：
  描述：

  3-[(1R)-2-hydroxy-1-phenylethyl]-6-methyl-3,6-diazabicyclo[3.1.0]hexane-2,4-dione 在 三乙胺 、 天然橡胶 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Use of Silicon-Based Tethers to Control Diastereofacial Selectivity in Azomethine Ylide Cycloadditions¹

  摘要：

  A novel approach to controlling the diastereofacial selectivity of intramolecular dipolar cycloadditions of azomethine ylides (cf. 9 --> 8) by varying the structure a silicon-based tether is described. A correlation is found between the length of the tether dipolarophile conjugate (TDC) and the observed sense of diastereocontrol. Azomethine ylides incorporating longer [OSiPh(2)OCH(2)CH(2)OCOCH=CH2], [OSi(i-Pr)(2)OSi(i-Pr)(2)OCH2CH=CH2], and [OSiPh(2)OCH(2)CH=CH2] TDCs favor endo-si attack (14 --> 16, 19 --> 20, and 21 --> 22) while the shorter TDC [OSiR(2)CH(2)CH=CH2] leads to a reversal in selectivity favoring the endo-re product (23a,b --> 24a,b). Structures of the cycloadducts have been assigned on the basis of selected X-ray diffraction data in combination with chemical/spectral correlation experiments. The work described herein represents a conceptually new approach to stereocontrol and extends the use of silicon-based tethers in asymmetric synthesis.

  DOI：

  10.1021/jo9609034