(4R)-N-crotonyl-4-phenyloxazolidin-2-one | 161970-61-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4R)-N-crotonyl-4-phenyloxazolidin-2-one
• 英文别名: (R)-3-but-2-enoyl-4-phenyl-oxazolidin-2-one；(4R)-3-but-2-enoyl-4-phenyl-1,3-oxazolidin-2-one
• CAS: 161970-61-2
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: DCVIMWRFFDRWJM-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R)-N-crotonyl-4-phenyloxazolidin-2-one 在 sodium tetrahydroborate 、 四氯化钛 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 7.0h， 生成 C₁₆H₂₁NO₃
  参考文献：
  名称：

  对映体形式全合成的碘甲烷内酯3a

  摘要：

  描述了海洋大环内酯异烟酰胺3a的正式全合成。合成的显着特征包括衍生自D -（-）-酒石酸的β-酮膦酸酯和衍生自L-谷氨酸的手性丁内酯的延伸。闭环复分解用于构建天然产物的大内酯核。

  DOI：

  10.1002/asia.201402593
• 作为产物：
  描述：

  (R)-4-苯基-2-唑烷酮 、 巴豆酰氯 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 (4R)-N-crotonyl-4-phenyloxazolidin-2-one
  参考文献：
  名称：

  Diastereoselective, large-scale synthesis of β-amino acids via asymmetric aza-Michael addition as α2δ ligands for the treatment of generalized anxiety disorder and insomnia

  摘要：

  Scalable synthetic routes to beta-amino acids 1 and 2 are presented. These two compounds, which bind to the alpha 2 delta subunit of calcium channels and have important medical applications, have been prepared on kilogram scale in our pilot plant through an improved synthesis that avoids the use of highly toxic reagents and hazardous chemistry present in the original Medicinal Chemistry route. The two chiral centers are introduced through asymmetric Michael and aza-Michael reactions with excellent diastereoselectivity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.08.119

文献信息

• [EN] IMIDAZOTRIAZINONE COMPOUNDS<br/>[FR] COMPOSÉS IMIDAZOTRIAZINONES
  申请人：ENVIVO PHARMACEUTICALS INC

  公开号：WO2012040230A1

  公开（公告）日：2012-03-29

  The present invention provides imidazotriazinone compounds which are inhibitors of phosphodiesterase 9. The present invention further provides processes, pharmaceutical compositions, pharmaceutical preparations and pharmaceutical use of the compounds in the treatment of PDE9 associated diseases or disorders in mammals, including CNS or neurodegeneration disorder.

  本发明提供了嘧啶三唑酮类化合物，这些化合物是磷酸二酯酶9的抑制剂。本发明还提供了在治疗哺乳动物中PDE9相关疾病或紊乱，包括中枢神经系统或神经退行性疾病中使用这些化合物的方法、药物组合物、药物制剂和药物用途。
• [EN] IMIDAZOTRIAZINONE COMPOUNDS<br/>[FR] COMPOSÉS D'IMIDAZOTRIAZINONE
  申请人：ENVIVO PHARMACEUTICALS INC

  公开号：WO2013142269A1

  公开（公告）日：2013-09-26

  The present invention provides imidazotriazinone compounds which are inhibitors of phosphodiesterase 9 and pharmaceutically acceptable salt thereof. The present invention further provides processes, pharmaceutical compositions, pharmaceutical preparations and pharmaceutical use of the compounds in the treatment of PDE9 associated diseases or disorders in mammals, including humans.

  本发明提供了咪唑三唑酮化合物，它们是磷酸二酯酶9的抑制剂及其药用盐。本发明还提供了用于治疗哺乳动物，包括人类，PDE9相关疾病或疾病的过程、药物组成、药物制剂和化合物的药用。
• Studies of intramolecular Diels–Alder reactions of nitroalkenes for the stereocontrolled synthesis of trans-decalin ring systems
  作者：David R. Williams、J. Cullen Klein、Nicholas S.C. Chow

  DOI：10.1016/j.tetlet.2010.11.012

  日期：2011.4

  Studies of thermal IMDA cyclizations of (1E,7E)-1-nitro-deca-1,7,9-trienes and (1E,3Z,7E)-1-nitro-deca-1,3,7,9-tetraenes have been examined. Reactions of these nitroalkenes proceed via transition states featuring characteristics of asymmetric stretch asynchronicity and result in stereoselective formation of trans-fused decalin products. Substantial rate acceleration is observed for IMDA cyclizations

  (1 E ,7 E )-1-nitro-deca-1,7,9-trienes 和 (1 E ,3 Z ,7 E )-1-nitro-deca-1,3,7的热 IMDA 环化研究,9-四烯已被检查。这些硝基烯烃的反应通过具有不对称拉伸异步特征的过渡态进行，并导致立体选择性形成反式融合十氢化萘产物。观察到 IMDA 环化的显着速率加速，以三烯14为例，这是由于束缚链中取代基的空间排斥，这促进了反式融合26 的容易立体控制的形成。
• Concise synthesis and confirmation of the absolute configurations of naturally occurring bioactive 2,7′-cyclolignans
  作者：Nannaphat Chumsri、Chutima Kuhakarn、Pawaret Leowanawat、Vichai Reutrakul、Darunee Soorukram

  DOI：10.1016/j.tetlet.2021.152827

  日期：2021.3

  A concise asymmetric synthesis of naturally occurring bioactive 2,7′-cyclolignans, namely 4,4′-dihydroxy-3′,5,5′-trimethoxy-2,7′-cyclolignan and 4,4′-dihydroxy-3,3′,5-trimethoxy-2,7′-cyclolignan, possessing the uncommon 8,8′-syn dimethyl stereochemistry and unsymmetrical C-6 units with 7′,8′-anti-orientation is described using a substrate-controlled stereoselective Friedel-Crafts cyclization as the

  天然存在的生物活性2,7'-cyclolignans的简明不对称合成，即4,4'-dihydroxy-3'，5,5'-trimethoxy-2,7'-cyclolignan和4,4'-dihydroxy-3,3使用受底物控制的立体选择性Friedel- F描述了具有罕见的8,8'-顺二甲基立体化学和具有7'，8'-反取向的不对称C-6单元的'，5-三甲氧基-2,7'-cyclolignan。工艺环化是关键步骤。以高产率获得具有高立体选择性的产物。天然4,4'-二羟基-3'，5,5'-三甲氧基-2,7'-cyclolignan和天然4,4'-二羟基-3,3'，5-三甲氧基-2的绝对构型7'-cyclolignan被指定为（7 'S，8 S，8 'S）和（7'R，8R，8'R），分别基于相应合成化合物的实验圆二色性（CD）光谱。
• Amino acids with affinity for the alpha2delta-protein
  申请人：Blazecka Garth Peter

  公开号：US20050101643A1

  公开（公告）日：2005-05-12

  Certain β-amino acids that bind to the alpha-2-delta (α2δ) subunit of a calcium channel are disclosed. These compounds and their pharmaceutically acceptable salts are useful in the treatment of a variety of psychiatric, pain and other disorders. Also disclosed are methods of making the β-amino acids.

  本发明揭示了结合到钙通道的α2δ亚基的某些β-氨基酸。这些化合物及其药学上可接受的盐在治疗各种精神疾病、疼痛和其他疾病方面非常有用。本发明还揭示了制备β-氨基酸的方法。