2-<2-(Tetrahydropyranyloxy)phenyl>propanol | 153623-49-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-<2-(Tetrahydropyranyloxy)phenyl>propanol
• 英文别名: 2-[2-(Oxan-2-yloxy)phenyl]propan-1-ol
• CAS: 153623-49-5
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: VFGYLTRUUCEQRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-<2-(Tetrahydropyranyloxy)phenyl>propanol 在 对甲苯磺酸 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 2-(2-hydroxyphenyl)propionaldehyde
  参考文献：
  名称：

  Asymmetric induction reactions. V. The palladium-catalyzed asymmetric .alpha.-allylation of carbonyl compounds with chiral allyl esters via enamines and imines

  摘要：

  A novel and excellent method for asymmetric alpha-allylation of carbonyl compounds via their chiral enamines or imines bearing allyl eaters has been developed. Readily available chiral allyl eaters having chirality at the alpha-position of the eater carbonyl group, such as (S)-proline and other (S)-alpha-amino acid allyl esters, have been found to serve as good asymmetric allylating reagents in palladium-catalyzed reactions of the chiral enamines and imines derived from them. The use of (S)-proline or (S)-valine allyl esters as the amino parts in the enamines or imines provided the highest optical yields of the corresponding alpha-allyl carbonyl compounds. A mechanism for asymmetric induction is proposed based on the stereochemical results obtained.

  DOI：

  10.1021/jo00080a033
• 作为产物：
  描述：

  2-羟基苯乙酸甲酯 在 lithium aluminium tetrahydride 、 lithium diisopropyl amide 、 三氯氧磷 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 29.5h， 生成 2-<2-(Tetrahydropyranyloxy)phenyl>propanol
  参考文献：
  名称：

  Asymmetric induction reactions. V. The palladium-catalyzed asymmetric .alpha.-allylation of carbonyl compounds with chiral allyl esters via enamines and imines

  摘要：

  A novel and excellent method for asymmetric alpha-allylation of carbonyl compounds via their chiral enamines or imines bearing allyl eaters has been developed. Readily available chiral allyl eaters having chirality at the alpha-position of the eater carbonyl group, such as (S)-proline and other (S)-alpha-amino acid allyl esters, have been found to serve as good asymmetric allylating reagents in palladium-catalyzed reactions of the chiral enamines and imines derived from them. The use of (S)-proline or (S)-valine allyl esters as the amino parts in the enamines or imines provided the highest optical yields of the corresponding alpha-allyl carbonyl compounds. A mechanism for asymmetric induction is proposed based on the stereochemical results obtained.

  DOI：

  10.1021/jo00080a033

文献信息

• Asymmetric induction reactions. V. The palladium-catalyzed asymmetric .alpha.-allylation of carbonyl compounds with chiral allyl esters via enamines and imines
  作者：Kunio Hiroi、Jun Abe、Kyoko Suya、Shuko Sato、Toshihiro Koyama

  DOI：10.1021/jo00080a033

  日期：1994.1

  A novel and excellent method for asymmetric alpha-allylation of carbonyl compounds via their chiral enamines or imines bearing allyl eaters has been developed. Readily available chiral allyl eaters having chirality at the alpha-position of the eater carbonyl group, such as (S)-proline and other (S)-alpha-amino acid allyl esters, have been found to serve as good asymmetric allylating reagents in palladium-catalyzed reactions of the chiral enamines and imines derived from them. The use of (S)-proline or (S)-valine allyl esters as the amino parts in the enamines or imines provided the highest optical yields of the corresponding alpha-allyl carbonyl compounds. A mechanism for asymmetric induction is proposed based on the stereochemical results obtained.