bicyclic (2R,5R,6R)-6-hydroxy-2-phenyl-3-oxa-1-azabicyclo<3.3.0>octan-8-one | 156045-79-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: bicyclic (2R,5R,6R)-6-hydroxy-2-phenyl-3-oxa-1-azabicyclo<3.3.0>octan-8-one
• 英文别名: (2R,5R,6S)-6-hydroxy-2-phenyl-3-oxa-1-aza-bicyclo<3.3.0>octane-8-one；(2R,5R,6S)-6-hydroxy-2-phenyl-3-oxa-1-azabicyclo<3.3.0>octane-8-one；(2R,5R,6S)-6-hydroxy-2-phenyl-3-oxa-1-azabicyclo[3.3.0]octane-8-one；Anvhfuzpeonrsh-jfgnbeqysa-；(3R,7S,7aR)-7-hydroxy-3-phenyl-3,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-5-one
• CAS: 156045-79-3
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: ANVHFUZPEONRSH-JFGNBEQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  bicyclic (2R,5R,6R)-6-hydroxy-2-phenyl-3-oxa-1-azabicyclo<3.3.0>octan-8-one 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以92%的产率得到(2R,3S)-1-benzyl-2-(hydroxymethyl)pyrrolidin-3-ol
  参考文献：
  名称：

  Chiral pool synthesis of trans-(2S3S)-3-hydroxyproline and castanodiol from S-pyroglutamic acid.

  摘要：

  The Pyroglutamic acid derivative 1 was converted through several steps into Castanodiol 9 and 2S,3S-3-Hydroxyproline 11. Key steps of the reaction sequence were the stereoselective epoxidation of 1 to 2 and the regioselective ring opening of 2 to 3. BH3.S(CH3)(2) reduction of the amide group of 3 and 4 resulted in a concomitant transformation of the acetal moiety into the N-benzyl protecting group. The air sensitive 5 and 6, were transformed to the stable N-Boc prolinol derivatives 7 and 8. Deprotection of 8 provided 9, while oxidation of 8 gave the protected proline derivative 10. Deprotection of 10 furnished enantiopure 2S,3S-3-Hydroxyproline 11.

  DOI：

  10.1016/s0957-4166(00)80492-9
• 作为产物：
  描述：

  (3R,7aS)-3-phenyl-6-(phenylselanyl)tetrahydro-3H,5H-pyrrolo[1,2-c]oxazol-5-one 在 叔丁基过氧化氢 、 aluminium amalgam 、 四丁基氟化铵 、 双氧水 、 碳酸氢钠 、 potassium carbonate 作用下， 以 四氢呋喃 、 异辛烷 、 乙醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 4.67h， 生成 bicyclic (2R,5R,6R)-6-hydroxy-2-phenyl-3-oxa-1-azabicyclo<3.3.0>octan-8-one
  参考文献：
  名称：

  Chiral pool synthesis of trans-(2S3S)-3-hydroxyproline and castanodiol from S-pyroglutamic acid.

  摘要：

  The Pyroglutamic acid derivative 1 was converted through several steps into Castanodiol 9 and 2S,3S-3-Hydroxyproline 11. Key steps of the reaction sequence were the stereoselective epoxidation of 1 to 2 and the regioselective ring opening of 2 to 3. BH3.S(CH3)(2) reduction of the amide group of 3 and 4 resulted in a concomitant transformation of the acetal moiety into the N-benzyl protecting group. The air sensitive 5 and 6, were transformed to the stable N-Boc prolinol derivatives 7 and 8. Deprotection of 8 provided 9, while oxidation of 8 gave the protected proline derivative 10. Deprotection of 10 furnished enantiopure 2S,3S-3-Hydroxyproline 11.

  DOI：

  10.1016/s0957-4166(00)80492-9

文献信息

• [EN] IMPROVED AMINOHYDROXYLATION OF ALKENES<br/>[FR] AMINOHYDROXYLATION AMÉLIORÉE D'ALCÈNES
  申请人：IND RES LTD

  公开号：WO2011159177A1

  公开（公告）日：2011-12-22

  The invention relates to a process for the aminohydroxylation of alkenes using N-oxycarbamate reagents, e.g. N-acyloxycarbamate, N-alkyloxycarbonyloxycarbamate and N-aralkoxycarbonyloxycarbamate reagents. The invention particularly relates to an intermolecular aminohydroxylation reaction that can be carried out in the absence of added base. The invention also relates to novel N-oxycarbamate reagents that are stable crystalline materials. The process of the invention is useful in the synthesis of compounds having a vicinal amino alcohol moiety, such as biologically active compounds.

  该发明涉及一种使用N-氧羰酸酯试剂（例如N-酰氧羰酸酯、N-烷氧羰酸酯和N-芳基氧羰酸酯试剂）对烯烃进行氨羟基化的方法。该发明特别涉及一种可以在无需添加碱的情况下进行的分子间氨羟基化反应。该发明还涉及新颖的N-氧羰酸酯试剂，这些试剂是稳定的结晶材料。该发明的方法在合成具有邻位氨基醇基团的化合物方面非常有用，例如具有生物活性的化合物。
• Intramolecular Mitsunobu reaction in the regio- and stereoselective synthesis of cis-4,5-disubstituted piperidin-2-ones
  作者：Nicole Langlois、Olivier Calvez

  DOI：10.1016/s0040-4039(00)01461-1

  日期：2000.10

  Enantiopure cis-4,5-disubstituted piperidin-2-ones were synthesized through the cyclization of O-benzyl hydroxamates under Mitsunobu conditions, followed by samarium diiodide reduction.

  通过在Mitsunobu条件下将O-苄基异羟肟酸酯环化，然后还原二碘化sa，合成了对映体纯的顺式-4,5-二取代的哌啶-2-酮。
• An Efficient Straightforward Synthesis of (-)-Bulgecinine
  作者：Sharad K. Panday、Nicole Langlois

  DOI：10.1080/00397919708006067

  日期：1997.4

  (-)-Bulgecinine 1, a component of the antibiotic bulgecins, was efficiently synthesized from (S)-pyroglutaminol 2.

  (−)-Bulgecinine 1，作为抗生素bulgecins的一种成分，已成功地从(S)-吡咯谷氨酰酒石酸盐2中高效合成。
• Diastereoselective Synthesis of (2S,3S,4S)-3-Hydroxy-4-methylproline, a Common Constituent of Several Antifungal Cyclopeptides
  作者：Nicole Langlois、Felaniaina Rakotondradany

  DOI：10.1016/s0040-4020(00)00117-4

  日期：2000.4

  (2S,3S,4S)-3-Hydroxy-4-methylproline 2 was synthesized from unsaturated gamma-lactams 4 and 5 derived from (S)-pyroglutaminol. Starting from 5, haplophilic effect in the hydrogenation of a 4-exo-methylenic intermediate improved the diastereoselectivity of the synthesis, which was achieved in 19% yield. (C) 2000 Elsevier Science Ltd. All rights reserved.

  (2S,3S,4S)-3-羟基-4-甲基脯氨酸2是从(S)-吡咯谷氨醇衍生而来的不饱和γ-内酰胺4和5合成的。从5开始，氢化过程中4-exo-甲基中间体的haplophilic效应提高了合成的对映选择性，收率为19%。© 2000 Elsevier Science Ltd. 保留所有权利。
• A Stereocontrolled Formal Asymmetric Synthesis of Pseudodistomin C
  作者：Ken-ichi Tanaka、Takuya Maesoba、Hiroyuki Sawanishi

  DOI：10.3987/com-05-10586

  日期：——

  An efficient and stereocontrolled formal asymmetric synthesis of pseudodistomin C has been achieved by employing intramolecular transamidation reaction, exo-methylenation, and highly stercoselective hydroboration. The resulting 2-hydroxymethylpiperidine derivative (15) was further converted into the key intermediate (2) for the synthesis of pseudodistomin C.

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