(R)-1-acetyl-5-isopropoxy-3-pyrrolin-2-one | 138259-70-8

• 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: (R)-1-acetyl-5-isopropoxy-3-pyrrolin-2-one
• 英文别名: 1-acetyl-5-isopropoxy-3-pyrrolin-2-one；(2R)-1-acetyl-2-propan-2-yloxy-2H-pyrrol-5-one
• CAS: 138259-70-8
• 化学式: C₉H₁₃NO₃
• 分子量: 183.207
• InChiKey: FNDNSXCVGOVFQD-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  (R)-1-acetyl-5-isopropoxy-3-pyrrolin-2-one 在 sodium hydride 、 三乙胺 、 lithium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 dimethyl 2-[(2R,3R)-1-acetyl-5-oxo-2-propan-2-yloxypyrrolidin-3-yl]-2-(3-methylbut-2-enyl)propanedioate
  参考文献：
  名称：

  Michael Additions to (R)-1-Acetyl-5-isopropoxy-3-pyrrolin-2-one and Subsequent N-Acyliminium Ion Generation:  Synthesis of Enantiopure 1-Azabicycles and Preparation of an Intermediate for a Projected Synthesis of Roseophilin

  摘要：

  DOI：

  10.1021/jo971854d
• 作为产物：
  描述：

  1-乙酰基-5-氧代-2,5-二氢-1H-吡咯-2-基乙酸酯 在 双(乙腈)氯化钯(II) 、 lipase B of Candida antarctica 作用下， 以 正己烷 、 二氯甲烷 、 叔丁醇 为溶剂， 反应 86.0h， 生成 (R)-1-acetyl-5-isopropoxy-3-pyrrolin-2-one
  参考文献：
  名称：

  Kinetic Resolutions and Enantioselective Transformations of 5-(Acyloxy)pyrrolinones Using Candida antarctica Lipase B:  Synthetic and Structural Aspects

  摘要：

  Various 5-(acyloxy)pyrrolinones have been prepared in enantiomerically pure form by means of an enzymatic resolution or an asymmetric transformation. Either enantiomer is obtained using the same enzyme, Candida antarctica lipase B, by modification of the procedure from transesterification to esterification. N-Acyl-5-(acyloxy)pyrrolinones 1 (R-2 = acyl) are synthesized by applying this method with 100% yield and >99% ee. To rationalize the observed enantioselectivity and the substituent effects of these reactions both empirical models and molecular modeling studies have been used, and a qualitative agreement was found between the results from these studies and the experimental results.

  DOI：

  10.1021/jo991062e

文献信息

• Enantioselective Rhodium-Catalyzed Isomerization of 4-Iminocrotonates: Asymmetric Synthesis of a Unique Chiral Synthon
  作者：Wen-Zhen Zhang、John C. K. Chu、Kevin M. Oberg、Tomislav Rovis

  DOI：10.1021/ja510348p

  日期：2015.1.21

  4-iminocrotonates catalyzed by a rhodium(I)/phosphoramidite complex is described. This reaction uses widely available amines to couple with 4-oxocrotonate to provide a convenient access to a central chiral building block in good yield and high enantioselectivity. Although the mechanism of this new transformation remains unclear, both Rh and the phosphoramidite play a central role.

  描述了由铑 (I)/亚磷酰胺复合物催化的 4-亚氨基巴豆酸酯的对映选择性异构化。该反应使用广泛可用的胺与 4-氧代巴豆酸酯偶联，从而以良好的收率和高对映选择性方便地获得中心手性结构单元。尽管这种新转变的机制尚不清楚，但 Rh 和亚磷酰胺都起着核心作用。
• Enantioselective palladium catalyzed allylic substitution of acyloxypyrrolinones by alcohols
  作者：Agnes D. Cuiper、Richard M. Kellogg

  DOI：10.1039/a800444g

  日期：——

  Chiral non-racemic acyloxypyrrolinones are converted into alkoxypyrrolinones with retention of configuration by a palladium catalyzed allylic substitution; this comprises a key step in a short chemo-enzymatic route to acyliminium ion precursors.

  通过钯催化的烯丙基取代作用，手性非气相酰氧基吡咯烷酮被转化为保留构型的烷氧基吡咯烷酮；这是酰亚胺离子前体的简短化学酶途径中的一个关键步骤。
• Stereochemistry of allylic alkylation of the tetracarbonyliron complexes of (R)-1-acetyl-5-isopropoxy-3-pyrrolin-2-one
  作者：Wim-Jan Koot、Henk Hiemstra、W. Nico Speckamp

  DOI：10.1039/c39930000156

  日期：——

  The two diastereoisomeric title complexes react with allyltrimethylsilane in the presence of BF3·Et2O to give nucleophilic substitution at C-5 to the corresponding 5-allyl derivatives; the reaction of the cis-complex proceeds slowly and with predominant inversion, whereas the trans-complex reacts quickly and with complete retention of configuration at C-5.

  在BF 3 ·Et 2 O的存在下，两种非对映异构体的标题配合物与烯丙基三甲基硅烷反应，在C-5处将亲核取代成相应的5-烯丙基衍生物；顺式-复合物的反应进行缓慢且具有明显的反转性，而反式-复合物反应迅速并且在C-5处完全保留构型。
• Alpha 2 Delta Ligands For Fibromyalgia and Other Disorders
  申请人：Dooley David James

  公开号：US20080207755A1

  公开（公告）日：2008-08-28

  This invention relates to a method of treating certain disorders by administering a compound of the formula 1 or a pharmaceutically acceptable salt thereof, wherein: R 1 is hydrogen, straight or branched alkyl of from 1 to 6 carbon atoms or phenyl; and R 2 is straight or branched alkyl of from 4 to 8 carbon atoms, straight or branched alkenyl of from 2 to 8 carbon atoms, cycloalkyl of from 3 to 7 carbon atoms, alkoxy of from 1 to 6 carbon atoms, -alkylcycloalkyl, -alkylalkoxy, -alkyl OH, -alkylphenyl, -alkylphenoxy, or -substituted phenyl. The invention also relates to a method of treating the above disorders by administering the compound (3S, 5R)-3-aminomethyl-5-methyl-octanoic acid.

  本发明涉及一种通过给予公式1化合物或其药学上可接受的盐来治疗某些疾病的方法，其中：R1是氢、1至6个碳原子的直链或支链烷基或苯基；R2是4至8个碳原子的直链或支链烷基、2至8个碳原子的直链或支链烯基、3至7个碳原子的环烷基、1至6个碳原子的烷氧基、-烷基环烷基、-烷基烷氧基、-烷基羟基、-烷基苯基、-烷基苯氧基或-取代苯基。本发明还涉及一种通过给予化合物(3S, 5R)-3-氨甲基-5-甲基-辛酸来治疗上述疾病的方法。
• ALPHA 2 DELTA LIGANDS FOR FIBROMYALGIA AND OTHER DISORDERS
  申请人：Dooley James David

  公开号：US20070027212A1

  公开（公告）日：2007-02-01

  This invention relates to a method of treating a disorder selected from OCD, agoraphobia, agoraphobia without history of panic disorder, specific phobia, social phobia, PTSD, restless legs syndrome, premenstrual dysphoric disorder, hot flashes, and fibromyalgia by administering a compound of the formula 1 or a pharmaceutically acceptable salt thereof, wherein: R 1 is hydrogen, straight or branched alkyl of from 1 to 6 carbon atoms or phenyl; and R 2 is straight or branched alkyl of from 4 to 8 carbon atoms, straight or branched alkenyl of from 2 to 8 carbon atoms, cycloalkyl of from 3 to 7 carbon atoms, alkoxy of from 1 to 6 carbon atoms, -alkylcycloalkyl, -alkylalkoxy, -alkyl OH, -alkylphenyl, -alkylphenoxy, or -substituted phenyl. The invention also relates to a method of treating the above disorders by administering the compound (3S,5R)-3-Aminomethyl-5-methyl-octanoic acid.

  本发明涉及通过给予式1化合物或其药学上可接受的盐治疗选自强迫症、广场恐惧症、无惊恐障碍史的广场恐惧症、特定恐惧症、社交恐惧症、创伤后应激障碍、不宁腿综合症、月经前期失调症、潮热和纤维肌痛的方法，其中：R1是氢、1至6个碳原子的直链或支链烷基或苯基；R2是4至8个碳原子的直链或支链烷基、2至8个碳原子的直链或支链烯基、3至7个碳原子的环烷基、1至6个碳原子的烷氧基、-烷基环烷基、-烷基烷氧基、-烷基-OH、-烷基苯基、-烷基苯氧基或-取代苯基。本发明还涉及通过给予化合物(3S,5R)-3-氨甲基-5-甲基-辛酸治疗上述疾病的方法。