α-<(R)-2-tetrahydropyranyloxy-2-phenylethyl>-α'-<(S)-2-tetrahydropyranyloxy-2-phenylethyl>-o-xylenedioxide | 167355-62-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: α-<(R)-2-tetrahydropyranyloxy-2-phenylethyl>-α'-<(S)-2-tetrahydropyranyloxy-2-phenylethyl>-o-xylenedioxide
• 英文别名: α-((R)-2-tetrahydropyranyloxy-2-phenylethyl)-α'-((S)-2-tetrahydropyranyloxy-2-phenylethyl)-o-xylenedioxide
• CAS: 167355-62-6
• 化学式: C₃₄H₄₂O₆
• 分子量: 546.704
• InChiKey: AUDMPEJHYMXCSI-GEZOHIFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.29
• 重原子数：
  40.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  α-<(R)-2-tetrahydropyranyloxy-2-phenylethyl>-α'-<(S)-2-tetrahydropyranyloxy-2-phenylethyl>-o-xylenedioxide 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 0.67h， 生成 α-<(R)-2-hydroxy-2-phenylethyl>-α'-<(S)-2-hydroxy-2-phenylethyl>-o-xylenedioxide
  参考文献：
  名称：

  Enantioselective protonation of samarium enolates by a C2-symmetric chiral diol

  摘要：

  High enantioselectivity (up to 97%ee) have been achieved in the protonation of samarium enolates which were generated by SmI2-mediated cross-coupling reaction between unsymmtrical dialkylketene and allyl iodide, using a C-2-symmetric chiral diol as a proton source. The stereochemistry of enolate formation and of the enantioselective protonation is discussed.

  DOI：

  10.1016/0957-4166(94)80086-3
• 作为产物：
  描述：

  (R)-Phenyl-[(tetrahydro-pyran-2-yloxy)]-acetic acid methyl ester 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 α-<(R)-2-tetrahydropyranyloxy-2-phenylethyl>-α'-<(S)-2-tetrahydropyranyloxy-2-phenylethyl>-o-xylenedioxide
  参考文献：
  名称：

  Enantioselective protonation of samarium enolates by a C2-symmetric chiral diol

  摘要：

  High enantioselectivity (up to 97%ee) have been achieved in the protonation of samarium enolates which were generated by SmI2-mediated cross-coupling reaction between unsymmtrical dialkylketene and allyl iodide, using a C-2-symmetric chiral diol as a proton source. The stereochemistry of enolate formation and of the enantioselective protonation is discussed.

  DOI：

  10.1016/0957-4166(94)80086-3