3-methyl-2-oxo-tetrahydro-furan-3-carbaldehyde | 55341-13-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 3-methyl-2-oxo-tetrahydro-furan-3-carbaldehyde
• 英文别名: rac-3-methyl-2-oxo-3,4,5-trihydrofuran-3-carbaldehyde；3-methyldihydro-2(3H)-furanon-3-ylcarboxaldehyde；3-Methyl-3-formyl-γ-butyrolacton；3-Methyl-2-oxooxolane-3-carbaldehyde
• CAS: 55341-13-4
• 化学式: C₆H₈O₃
• 分子量: 128.128
• InChiKey: YDXSEFRDFYVFSA-UHFFFAOYSA-N

物化性质

• 沸点：
  261.9±33.0 °C(Predicted)
• 密度：
  1.1610 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methyl-2-oxo-tetrahydro-furan-3-carbaldehyde 在 zinc(II) tetrahydroborate 、 柠檬酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以50%的产率得到3-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  Internally Masked Neopentyl Sulfonyl Ester Cyclization Release Prodrugs of Acamprosate, Compositions Thereof, and Methods of Use

  摘要：

  内部掩盖的新戊基磺酰酯前药，包含这种前药的药物组合物，以及使用这种前药和组合物治疗疾病的方法被披露。具体来说，披露了展现增强口服生物利用度的阿卡姆普罗酸前药以及使用阿卡姆普罗酸前药治疗神经退行性疾病、精神障碍、情绪障碍、焦虑障碍、躯体形式障碍、运动障碍、物质滥用障碍、暴饮暴食障碍、皮层扩散性抑郁相关障碍、耳鸣、睡眠障碍、多发性硬化症和疼痛的方法。

  公开号：

  US20090099253A1
• 作为产物：
  描述：

  2-甲烯基丁内酯 、 一氧化碳 在 η⁶-C6H6BPh3^-Rh(COD)⁺ 、 1,4-双(二苯基膦)丁烷 氢气 作用下， 以 二氯甲烷 为溶剂， 130.0 ℃ 、4.14 MPa 条件下， 反应 24.0h， 以56%的产率得到3-methyl-2-oxo-tetrahydro-furan-3-carbaldehyde
  参考文献：
  名称：

  Excellent regiochemical control in the hydroformylation of .alpha.,.beta.-unsaturated esters catalyzed by zwitterionic rhodium complexes and 1,4-bis(diphenylphosphino)butane

  摘要：

  DOI：

  10.1021/jo00039a042

文献信息

• Influence of 1,4-Bis(diphenylphosphino)butane on the Hydroformylation of .alpha.,.beta.-Unsaturated Esters Catalyzed by Zwitterionic, Cationic, and Neutral Rhodium(I) Complexes. The Asymmetric Hydroformylation of .alpha.-Methylene-.gamma.-Butyrolactone
  作者：Chul Woo Lee、Howard Alper

  DOI：10.1021/jo00108a007

  日期：1995.2

  An investigation was made of the effect of 1,4-bis(diphenylphosphino)butane (dppb) on the regioselectivity of the hydroformylation of alpha,beta>-unsaturated esters with synthesis gas, catalyzed by rhodium(I) complexes. Excellent regioselectivity was obtained when dppb was added as a ligand for the reaction of methyl acrylate and alpha-methylene-gamma-butyrolactone with synthesis gas. However, it inhibits the reaction when methyl methacrylate is used as the substrate. The asymmetric hydroformylation of alpha-methylene-gamma-butyrolactone using [Rh(1,5-hd)(phen)]Cl-+(-) as the catalyst and (R)-BINAP as the chiral ligand (6:1 ratio of(R)-BINAP/Rh) gave an aldehydic lactone, containing a quaternary chiral center, in up to 37% ee.
• GRANDBERG I. I.; TOKMAKOV G. P., XIMIYA GETEROTSIKL. SOEDIN. <KGSS-AQ>, 1975, HO 2, 207-10
  作者：GRANDBERG I. I.、 TOKMAKOV G. P.

  DOI：——

  日期：——
• [EN] HYDROFORMYLATION PROCESS
  申请人：UNIVERSITE D'OTTAWA/UNIVERSITY OF OTTAWA

  公开号：WO1993014057A1

  公开（公告）日：1993-07-22

  (EN) A process for the production of an aldehyde from an olefin (e.g. a functionalised olefin) is provided. The process comprises reacting the olefin with carbon monoxide and hydrogen and/or a reducing agent in the liquid phase in the presence of a soluble catalyst comprising a Zwitterionic rhodium complex and a bidentate phosphine ligand. The process is suitably carried out on an elevated temperature in the range 70 to 120 °C.(FR) Un procédé pour la production d'un aldéhyde à partir d'une oléfine (par exemple une oléfine fonctionnalisée) est décrit. Le procédé comprend la réaction de l'oléfine avec le monoxyde de carbone et l'hydrogène et/ou un agent réducteur, en phase liquide, en présence d'un catalyseur soluble comprenant un complexe zwitterionique de rhodium et un ligand phosphine bidentate. Le procédé s'effectue de manière adéquate à une température élevée, de l'ordre de 70 à 120 °C.
• [EN] INTERNALLY MASKED NEOPENTYL SULFONYL ESTER CYCLIZATION RELEASE PRODRUGS OF ACAMPROSATE, COMPOSITIONS THEREOF, AND METHODS OF USE<br/>[FR] PROMÉDICAMENTS DE L'ACAMPROSATE À LIBÉRATION PAR CYCLISATION DE NÉOPENTYLSULFONYLESTER À MASQUAGE INTERNE, LEURS COMPOSITIONS ET PROCÉDÉS D'UTILISATION
  申请人：XENOPORT INC

  公开号：WO2009052191A1

  公开（公告）日：2009-04-23

  Internally masked neopentyl sulfonyl ester prodrugs of acamprosate, pharmaceutical compositions comprising such prodrugs, and methods of using such prodrugs and compositions thereof for treating diseases are disclosed. In particular, acamprosate prodrugs exhibiting enhanced oral bioavailability and methods of using acamprosate prodrugs to treat neurodegenerative disorders, psychotic disorders, mood disorders, anxiety disorders, somatoform disorders, movement disorders, substance abuse disorders, binge eating disorder, cortical spreading depression related disorders, tinnitus, sleeping disorders, multiple sclerosis, and pain are disclosed.
• Internally Masked Neopentyl Sulfonyl Ester Cyclization Release Prodrugs of Acamprosate, Compositions Thereof, and Methods of Use
  申请人：Li Yunxiao

  公开号：US20090099253A1

  公开（公告）日：2009-04-16

  Internally masked neopentyl sulfonyl ester prodrugs of acamprosate, pharmaceutical compositions comprising such prodrugs, and methods of using such prodrugs and compositions thereof for treating diseases are disclosed. In particular, acamprosate prodrugs exhibiting enhanced oral bioavailability and methods of using acamprosate prodrugs to treat neurodegenerative disorders, psychotic disorders, mood disorders, anxiety disorders, somatoform disorders, movement disorders, substance abuse disorders, binge eating disorder, cortical spreading depression related disorders, tinnitus, sleeping disorders, multiple sclerosis, and pain are disclosed.

  内部掩盖的新戊基磺酰酯前药，包含这种前药的药物组合物，以及使用这种前药和组合物治疗疾病的方法被披露。具体来说，披露了展现增强口服生物利用度的阿卡姆普罗酸前药以及使用阿卡姆普罗酸前药治疗神经退行性疾病、精神障碍、情绪障碍、焦虑障碍、躯体形式障碍、运动障碍、物质滥用障碍、暴饮暴食障碍、皮层扩散性抑郁相关障碍、耳鸣、睡眠障碍、多发性硬化症和疼痛的方法。