Methyl 2-<2-(tetrahydropyranyloxy)phenyl>propionate | 153623-47-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: Methyl 2-<2-(tetrahydropyranyloxy)phenyl>propionate
• 英文别名: Methyl 2-methyl-2-(2-tetrahydropyran-2-yloxyphenyl)acetate；methyl 2-[2-(oxan-2-yloxy)phenyl]propanoate
• CAS: 153623-47-3
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: DQBACQPOHCRGTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl 2-<2-(tetrahydropyranyloxy)phenyl>propionate 在 lithium aluminium tetrahydride 、 对甲苯磺酸 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 35.0h， 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 diisopropyl amide 、 三氯氧磷 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 13.5h， 生成 Methyl 2-<2-(tetrahydropyranyloxy)phenyl>propionate
  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

• .beta.-Adrenergic blocking agents in the 1,2,3-thiadiazole series
  申请人：Syntex (U.S.A.) Inc.

  公开号：US03940407A1

  公开（公告）日：1976-02-24

  Novel 4-[2,3 or 4(3-amino-2-hydroxypropoxy) phenyl]- and 5-[2,3 or 4(3-amino-2-hydroxypropoxy) phenyl]-1,2,3-thiadiazole derivatives which may be further substituted at the C-5 or C-4 position of the thiadiazole ring, respectively, by a lower alkyl, phenyl, trifluoromethyl, carboxy, alkoxycarbonyl, cyano or an aminocarbonyl group, and the pharmaceutically acceptable acid addition salts thereof and processes for the production of such compounds; 4-[4(3-t-butylamino-2-hydroxypropoxy)phenyl]-1,2,3-thiadiazole and 5-[4(3-t-butylamino-2-hydroxypropoxy)phenyl]-1,2,3-thiadiazole are representative of the class. These compounds possess cardiovascular activity and are useful for the treatment of abnormal heart conditions in mammals.

  这是一种新型的衍生物，名称为4-[2,3或4-(3-氨基-2-羟基丙氧基)苯基]-和5-[2,3或4-(3-氨基-2-羟基丙氧基)苯基]-1,2,3-噻二唑，它们可以在噻二唑环的C-5或C-4位置进一步取代，分别为较低的烷基、苯基、三氟甲基、羧基、烷氧基羰基、氰基或氨基羰基基团，以及它们的药用可接受的酸盐和制备这些化合物的过程；4-[4-(3-t-丁基氨基-2-羟基丙氧基)苯基]-1,2,3-噻二唑和5-[4-(3-t-丁基氨基-2-羟基丙氧基)苯基]-1,2,3-噻二唑是该类化合物的代表。这些化合物具有心血管活性，可用于治疗哺乳动物的异常心脏病状。
• US3940407A
  申请人：——

  公开号：US3940407A

  公开（公告）日：1976-02-24
• 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.