(5S)-1-(4-methoxybenzyl)-5,6-dihydroxypiperidin-2-one | 1029421-38-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (5S)-1-(4-methoxybenzyl)-5,6-dihydroxypiperidin-2-one
• 英文别名: (5S)-5,6-dihydroxy-1-[(4-methoxyphenyl)methyl]piperidin-2-one
• CAS: 1029421-38-2
• 化学式: C₁₃H₁₇NO₄
• 分子量: 251.282
• InChiKey: JBIJGGDFGCKFMT-AMGKYWFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  70
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  异丁腈 、 (5S)-1-(4-methoxybenzyl)-5,6-dihydroxypiperidin-2-one 在 三氟化硼乙醚 作用下， 以91%的产率得到(+/-)-(3aR,7aS)-4-(4-methoxybenzyl)-3a,4,7,7a-tetrahydro-2-isopropyloxazolo[b]pyridin-5(6H)-one
  参考文献：
  名称：

  Diastereoselective Ritter Reactions of Chiral Cyclic N-Acyliminium Ions:  Synthesis of Pyrido- and Pyrrolo[2,3-d]oxazoles and 4-Hydroxy-5-N-acylaminopyrrolidines and 5-Hydroxy-6-N-acylaminopiperidines

  摘要：

  Pyrido- and pyrrolo[2,3-d]oxazoles can be conveniently prepared in high yield from the Ritter reaction of nitriles and in situ generated chiral cyclic N-acyliminium ions. cis-4-Hydroxy-5-acylaminopyrrolidines and cis-5-hydroxy-6-acylaminopiperidines can be readily obtained by acid hydrolysis of these bicyclic heterocyclic compounds, respectively.

  DOI：

  10.1021/jo800007g
• 作为产物：
  描述：

  (S)-3-hydroxy-1-(4-methoxybenzyl)-2,6-piperidinedione 在 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.67h， 以48%的产率得到(5S)-1-(4-methoxybenzyl)-5,6-dihydroxypiperidin-2-one
  参考文献：
  名称：

  对环N-酰基亚胺离子的非对映选择性硼诺-曼尼希反应

  摘要：

  已将硼酸加至五元和六元环N-酰基亚胺离子上以非对映选择性方式分别制备5-和6-取代的4-羟基吡咯烷酮-2-酮和5-羟基哌啶-2-酮。 。

  DOI：

  10.1016/j.tet.2007.11.046

文献信息

• Metal-Catalyzed Cycloisomerization Reactions of <i>cis</i>-4-Hydroxy-5-alkynylpyrrolidinones and <i>cis</i>-5-Hydroxy-6-alkynylpiperidinones: Synthesis of Furo[3,2-<i>b</i>]pyrroles and Furo[3,2-<i>b</i>]pyridines
  作者：Jasmine C. Jury、Nalivela Kumara Swamy、Arife Yazici、Anthony C. Willis、Stephen G. Pyne

  DOI：10.1021/jo9007942

  日期：2009.8.7

  Furo[3,2-b]pyrroles and furo[3,2-b]pyridines can be conveniently prepared in good yields from the cycloisomerization reactions of cis-4-hydroxy-5-alkynylpyrrolidinones and cis-5-hydroxy-6-alkynylpiperidinones, respectively, using Ag(I), Pd(II)/Cu(I), or Au(I) catalysis. In one case, the cycloisomerization product was unstable and produced a furan derivative by a ring-opening reaction.

  顺式-4-羟基-5-炔基吡咯烷酮与顺式-5-羟基-6-炔基哌啶子酮的环异构化反应可方便地以高收率制备呋喃并[3,2- b ]吡咯和呋喃[3,2- b ]吡啶分别使用Ag（I），Pd（II）/ Cu（I）或Au（I）催化。在一种情况下，环异构化产物不稳定并且通过开环反应产生呋喃衍生物。
• Diastereoselective Ritter Reactions of Chiral Cyclic <i>N</i>-Acyliminium Ions:  Synthesis of Pyrido- and Pyrrolo[2,3-<i>d</i>]oxazoles and 4-Hydroxy-5-<i>N</i>-acylaminopyrrolidines and 5-Hydroxy-6-<i>N</i>-acylaminopiperidines
  作者：Ian R. Morgan、Arife Yazici、Stephen G. Pyne、Brian W. Skelton

  DOI：10.1021/jo800007g

  日期：2008.4.1

  Pyrido- and pyrrolo[2,3-d]oxazoles can be conveniently prepared in high yield from the Ritter reaction of nitriles and in situ generated chiral cyclic N-acyliminium ions. cis-4-Hydroxy-5-acylaminopyrrolidines and cis-5-hydroxy-6-acylaminopiperidines can be readily obtained by acid hydrolysis of these bicyclic heterocyclic compounds, respectively.
• Diastereoselective borono-Mannich reactions on cyclic N-acyliminium ions
  作者：Ian R. Morgan、Arife Yazici、Stephen G. Pyne

  DOI：10.1016/j.tet.2007.11.046

  日期：2008.2

  The addition of boronic acids to five- and six-membered ring N-acyliminium ions has been employed to prepare 5- and 6-substituted 4-hydroxypyrrolidin-2-ones and 5-hydroxypiperidin-2-ones, respectively, in a diastereoselective fashion.

  已将硼酸加至五元和六元环N-酰基亚胺离子上以非对映选择性方式分别制备5-和6-取代的4-羟基吡咯烷酮-2-酮和5-羟基哌啶-2-酮。 。