3-[(1R)-2-[diphenyl(prop-2-enyl)silyl]oxy-1-phenylethyl]-6-methyl-3,6-diazabicyclo[3.1.0]hexane-2,4-dione | 185805-28-1

• 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: 3-[(1R)-2-[diphenyl(prop-2-enyl)silyl]oxy-1-phenylethyl]-6-methyl-3,6-diazabicyclo[3.1.0]hexane-2,4-dione
• CAS: 185805-28-1
• 化学式: C₂₈H₂₈N₂O₃Si
• 分子量: 468.627
• InChiKey: YQZOIYKVFLFPMQ-VIIRMWRASA-N

物化性质

• 沸点：
  590.5±50.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.74
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  49.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[(1R)-2-[diphenyl(prop-2-enyl)silyl]oxy-1-phenylethyl]-6-methyl-3,6-diazabicyclo[3.1.0]hexane-2,4-dione 在 天然橡胶 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Tether-Mediated Stereocontrol in Intramolecular Azomethine Ylide Cycloadditions

  摘要：

  The computationally guided design of a silicon-based tether system for stereoselective intramolecular azomethine ylide cycloadditions is described.

  DOI：

  10.1021/jo00101a005
• 作为产物：
  描述：

  allylchlorodiphenylsilane 、 3-[(1R)-2-hydroxy-1-phenylethyl]-6-methyl-3,6-diazabicyclo[3.1.0]hexane-2,4-dione 在 三乙胺 作用下， 以78%的产率得到3-[(1R)-2-[diphenyl(prop-2-enyl)silyl]oxy-1-phenylethyl]-6-methyl-3,6-diazabicyclo[3.1.0]hexane-2,4-dione
  参考文献：
  名称：

  Tether-Mediated Stereocontrol in Intramolecular Azomethine Ylide Cycloadditions

  摘要：

  The computationally guided design of a silicon-based tether system for stereoselective intramolecular azomethine ylide cycloadditions is described.

  DOI：

  10.1021/jo00101a005

文献信息

• Use of Silicon-Based Tethers to Control Diastereofacial Selectivity in Azomethine Ylide Cycloadditions¹
  作者：Philip Garner、Philip B. Cox、James T. Anderson、John Protasiewicz、Rebecca Zaniewski

  DOI：10.1021/jo9609034

  日期：1997.2.1

  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.
• Tether-Mediated Stereocontrol in Intramolecular Azomethine Ylide Cycloadditions
  作者：Philip P. Garner、Philip B. Cox、Stephen J. Klippenstein、Wiley J. Youngs、David B. McConville

  DOI：10.1021/jo00101a005

  日期：1994.11

  The computationally guided design of a silicon-based tether system for stereoselective intramolecular azomethine ylide cycloadditions is described.