(4R,5S)-5-(1-naphthyl)-4-[(S)-2-octyloxycarbonyl]-2-phenyl-4,5-dihydrooxazole | 945656-30-4

• 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: (4R,5S)-5-(1-naphthyl)-4-[(S)-2-octyloxycarbonyl]-2-phenyl-4,5-dihydrooxazole
• 英文别名: [(2S)-octan-2-yl] (4R,5S)-5-naphthalen-1-yl-2-phenyl-4,5-dihydro-1,3-oxazole-4-carboxylate
• CAS: 945656-30-4
• 化学式: C₂₈H₃₁NO₃
• 分子量: 429.559
• InChiKey: GBFJUOPRGNWPOD-LZYPDUGYSA-N

物化性质

• 沸点：
  584.0±50.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (Z)-2-phenyl-4-(1-naphthylmethylene)-5(4H)-oxazolone 在 4-二甲氨基吡啶 、 二乙氨基乙醇 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 生成 (S)-2-octyl (Z)-2-benzoylamino-3-(1-naphthyl)-2-propenoate 、 (4R,5R)-5-(1-naphthyl)-4-[(S)-2-octyloxycarbonyl]-2-phenyl-4,5-dihydrooxazole 、 (4S,5R)-5-(1-naphthyl)-4-[(S)-2-octyloxycarbonyl]-2-phenyl-4,5-dihydrooxazole 、 (4R,5S)-5-(1-naphthyl)-4-[(S)-2-octyloxycarbonyl]-2-phenyl-4,5-dihydrooxazole 、 (4S,5S)-5-(1-naphthyl)-4-[(S)-2-octyloxycarbonyl]-2-phenyl-4,5-dihydrooxazole
  参考文献：
  名称：

  Asymmetric Cyclization Reactions of N-Benzoyl-α-dehydroarylalanine Alkyl Esters via Photoinduced Electron Transfer from Achiral and Chiral Amines

  摘要：

  Irradiation of the title compounds [(Z)-1] having (S)-(+)-sec-butyl, (-)-menthyl, and related chiral auxiliaries in methanol and 1,2-dichloroethane containing 2-(diethylamino)ethanol afforded chiral auxiliary-substituted (4S,5S)-, (4R,5R)-, (4R,5S)-, and (4S,5R)-4,5-dihydrooxazole derivatives (2) along with (E)-1. It was found that the photoinduced electron transfer-initiated cyclization of (Z)-1 gives either of the two diastereomers for cis-2 and trans-2 in diastereomeric excess whose value varies from 8 to 81% depending on the property of solvent as well as on the steric bulkiness of chiral auxiliary. On the other hand, the asymmetric photocyclization of chiral auxiliary-unsubstituted (Z)-1 in 1,2-dichloroethane proceeded cleanly in the presence of the chiral amine, (S)-(-)-1-methylpyrrolidine-2-methanol, to give (4R,5R)-2 and (4R,5S)-2 in enantiomeric excess of 17-38% and 20-33%, respectively, depending on the steric bulkiness of the aryl substituent. A mechanistic consideration of these diastereoselective and enantioselective photocyclization reactions enabled us to propose major factors controlling the extent of asymmetric photoinduction.

  DOI：

  10.3987/com-11-12193

文献信息

• Asymmetric Cyclization Reactions of N-Benzoyl-α-dehydroarylalanine Alkyl Esters via Photoinduced Electron Transfer from Achiral and Chiral Amines
  作者：Tadamitsu Sakurai、Haruo Watanabe、Tetsutaro Igarashi、Yuji Sasaki

  DOI：10.3987/com-11-12193

  日期：——

  Irradiation of the title compounds [(Z)-1] having (S)-(+)-sec-butyl, (-)-menthyl, and related chiral auxiliaries in methanol and 1,2-dichloroethane containing 2-(diethylamino)ethanol afforded chiral auxiliary-substituted (4S,5S)-, (4R,5R)-, (4R,5S)-, and (4S,5R)-4,5-dihydrooxazole derivatives (2) along with (E)-1. It was found that the photoinduced electron transfer-initiated cyclization of (Z)-1 gives either of the two diastereomers for cis-2 and trans-2 in diastereomeric excess whose value varies from 8 to 81% depending on the property of solvent as well as on the steric bulkiness of chiral auxiliary. On the other hand, the asymmetric photocyclization of chiral auxiliary-unsubstituted (Z)-1 in 1,2-dichloroethane proceeded cleanly in the presence of the chiral amine, (S)-(-)-1-methylpyrrolidine-2-methanol, to give (4R,5R)-2 and (4R,5S)-2 in enantiomeric excess of 17-38% and 20-33%, respectively, depending on the steric bulkiness of the aryl substituent. A mechanistic consideration of these diastereoselective and enantioselective photocyclization reactions enabled us to propose major factors controlling the extent of asymmetric photoinduction.