(5S,3E)-5-benzyloxy-6-hydroxy-hex-3-en-2-one | 153186-37-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (5S,3E)-5-benzyloxy-6-hydroxy-hex-3-en-2-one
• 英文别名: (E,5S)-6-hydroxy-5-phenylmethoxyhex-3-en-2-one
• CAS: 153186-37-9
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: BYUARGYMWNPZQA-GWJCSSMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5S,3E)-5-benzyloxy-6-hydroxy-hex-3-en-2-one 在 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.25h， 生成 Acrylic acid (E)-(S)-2-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hexa-3,5-dienyl ester
  参考文献：
  名称：

  Chiral dienes from enantiomerically pure enones. Highly stereoselective intramolecular Diels–Alder reaction involving ethenesulfonates

  摘要：

  Chiral dienes 2, easily prepared from alpha,beta-unsaturated gamma-alkoxy ketones, are subjected to inter- and intramolecular Diels-Alder reactions, Intermolecular cycloadditions of dienes 2 with 4-phenyl-1,2,4-triazole-3,5(2H)-dione 3 are found to be diastereoselective, Thermal or high pressure-induced intramolecular cycloadditions of trienes 8, featuring a sulfonate moiety connecting a diene and a dienophile, are found to proceed with high diastereoselectivity to give sultones 11 and 12. An interesting domino process is observed when enone 5 is reacted with sodium hydride. In this reaction sequence, the decahydropyrano [2,3,4-de]chromene derivative 15 was formed, NMR spectroscopic studies allowed the assignments of the configurations of the bi- and tri-cyclic products.

  DOI：

  10.1039/p19960002297
• 作为产物：
  描述：

  (R)-2-benzyloxy-3-hydroxy-propionaldehyde 、 1-三苯基膦-2-丙酮 以 Petroleum ether 、 苯 为溶剂， 反应 24.0h， 以82%的产率得到(5S,3E)-5-benzyloxy-6-hydroxy-hex-3-en-2-one
  参考文献：
  名称：

  重氮化合物与烯酮的环加成的非对面选择性

  摘要：

  手性α，β不饱和γ -烷氧基或γ氨基酮（烯酮）1用在以立体选择性方式重氮化合物，得到偶联反应Δ 2 -pyrazolines 5和6。在所有情况下SYN -选择性环加成进行了观察。在较低的温度下，非对映异构体比例有所提高，但是没有观察到高压的显着影响。用相同的烯酮1的（E）和（Z）衍生物进行该反应，得到相同的产物。

  DOI：

  10.1016/0040-4020(94)01049-6

文献信息

• Synthesis of enantiomerically pure pyrrolidines by stereospecific cycloaddition of azomethine ylides with enones
  作者：M. Pätzel、G. Galley、P.G. Jones、A. Chrapkowsky

  DOI：10.1016/s0040-4039(00)73839-1

  日期：1993.9

  alkoxy or amino substituent in γ-position react with azomethine ylides 3 (obtained from glycine imines) in the presence of DBU/AgOAc giving enantiomerically pure pyrrolidine derivatives 4 in a stereospecific manner.

  在DBU / AgOAc的存在下，几种在γ位带有手性烷氧基或氨基取代基的（E）-α，β-不饱和酮（烯酮）2与偶氮甲亚胺3（由甘氨酸亚胺获得）反应，得到对映体纯的吡咯烷衍生物4以立体定向的方式。
• Polyfunctionalized Pyrrolidines by Stereoselective 1,3-Dipolar Cycloaddition of Azomethine Ylides to Chiral Enones
  作者：Guido Galley、Juergen Liebscher、Michael Paetzel

  DOI：10.1021/jo00121a019

  日期：1995.8

  The cycloaddition reactions of chiral alpha,beta-unsaturated ketones substituted by alkoxy or amino groups in the gamma-position to azomethine ylides (obtained from glycine imines) were investigated in the presence of a base, LiBr and AgOAc. High regioselectivities were observed in most cases, resulting in the formation of a single diastereomer, particularly if a DBU/AgOAc catalyst system was employed. The influence of reaction conditions and olefin structure on the stereoselectivity of the reaction was investigated, and models rationalizing stereocontrol are proposed. In addition, an interesting deconjugation reaction of acetals derived from gamma,delta-dihydroxy alpha,beta-unsaturated enones or esters is described.
• Diastereofacial selectivity of the cycloaddition of diazo compounds to enones
  作者：G Galley、M Pätzel、P.G Jones

  DOI：10.1016/0040-4020(94)01049-6

  日期：1995.2

  Chiral α,β-unsaturated γ-alkoxy- or γ-amino-ketones (enones) 1 react with diazo compounds in a stereoselective manner affording conjugated Δ2-pyrazolines 5 and 6. In all cases syn-selectivity for the cycloaddition was observed. The diastereomeric ratio is improved at lower temperatures, but no significant influence of high pressure is observed. Carrying out this reaction with (E) and (Z) derivatives

  手性α，β不饱和γ -烷氧基或γ氨基酮（烯酮）1用在以立体选择性方式重氮化合物，得到偶联反应Δ 2 -pyrazolines 5和6。在所有情况下SYN -选择性环加成进行了观察。在较低的温度下，非对映异构体比例有所提高，但是没有观察到高压的显着影响。用相同的烯酮1的（E）和（Z）衍生物进行该反应，得到相同的产物。
• Chiral dienes from enantiomerically pure enones. Highly stereoselective intramolecular Diels–Alder reaction involving ethenesulfonates
  作者：Guido Galley、Michael Pätzel

  DOI：10.1039/p19960002297

  日期：——

  Chiral dienes 2, easily prepared from alpha,beta-unsaturated gamma-alkoxy ketones, are subjected to inter- and intramolecular Diels-Alder reactions, Intermolecular cycloadditions of dienes 2 with 4-phenyl-1,2,4-triazole-3,5(2H)-dione 3 are found to be diastereoselective, Thermal or high pressure-induced intramolecular cycloadditions of trienes 8, featuring a sulfonate moiety connecting a diene and a dienophile, are found to proceed with high diastereoselectivity to give sultones 11 and 12. An interesting domino process is observed when enone 5 is reacted with sodium hydride. In this reaction sequence, the decahydropyrano [2,3,4-de]chromene derivative 15 was formed, NMR spectroscopic studies allowed the assignments of the configurations of the bi- and tri-cyclic products.