α-Methoxycarbonyl-α-methyl-γ-butyrolacton | 41255-44-1

• 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: α-Methoxycarbonyl-α-methyl-γ-butyrolacton
• 英文别名: 3-methyl-2-oxo-tetrahydro-furan-3-carboxylic acid methyl ester；Methyl 3-methyl-2-oxooxolane-3-carboxylate
• CAS: 41255-44-1
• 化学式: C₇H₁₀O₄
• 分子量: 158.154
• InChiKey: HQSGNHUICRTCEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2S,3R)-3-Methyl-2-tributylstannanyl-tetrahydro-furan-3-carboxylic acid methyl ester 在 吡啶 、 chromium(VI) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 以26%的产率得到α-Methoxycarbonyl-α-methyl-γ-butyrolacton
  参考文献：
  名称：

  α-Alkoxystannyl ethers in organic synthesis: Synthesis of functionalised γ-butyrolactones

  摘要：

  Ozonolysis of a variety of (tetraydrofuran-2-yl)tri-n-butylstannanes affords the corresponding gamma-butyrolactones in good to excellent yields, This reaction is tolerant to a range of other functional groups and provides access to substituted gamma-butyrolactones not available from aldol reactions of the parent lactone. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4039(96)02100-4

文献信息

• Process for the preparation of alkyl 1-methylcyclopropanecarboxylate
  申请人：——

  公开号：US20020016493A1

  公开（公告）日：2002-02-07

  Disclosed is a 4-step process for the preparation of alkyl esters of 1-methylcyclopropanecarboxylic acid which comprises the steps of (1) converting &ggr;-butyrolactone to &agr;-methyl-&ggr;-butyrolactone; (2) converting the &agr;-methyl-&ggr;-butyrolactone from step (1) to an alkyl 4-halo-2-methylbutyrate; (3) producing a xylene solution of the alkyl 4-halo-2-methylbutyrate; and (4) contacting the xylene solution of an alkyl 4-halo-2-methylbutyrate from step (3) with an alkali metal alkoxide under conditions of temperature and pressure which causes vaporization of (i) an alkanol as it is formed and (ii) an alkyl 1-methylcyclopropanecarboxylate as it is formed from the alkyl 4-halo-2-methylbutyrate. Also disclosed are processes whereby the alkyl 1-methylcyclopropanecarboxylate, prepared as described above, is converted to 1-methylcyclopropylamine.

  揭示了一种制备1-甲基环丙烷羧酸烷基酯的4步过程，包括以下步骤：(1) 将γ-丁内酯转化为α-甲基-γ-丁内酯；(2) 将步骤(1)中的α-甲基-γ-丁内酯转化为烷基4-卤代-2-甲基丁酸酯；(3) 生成烷基4-卤代-2-甲基丁酸酯的二甲苯溶液；以及(4) 将步骤(3)中的烷基4-卤代-2-甲基丁酸酯的二甲苯溶液与一种碱金属烷氧化物接触，在温度和压力条件下造成（i）烷醇的汽化，因为它形成，以及（ii）从烷基4-卤代-2-甲基丁酸酯形成的烷基1-甲基环丙烷羧酸酯的汽化。还揭示了一种过程，其中根据上述描述制备的烷基1-甲基环丙烷羧酸酯被转化为1-甲基环丙基胺。
• A stereospecific total synthesis of (.+-.)-methylenomycin A and its epimer, (.+-.)-epimethylenomycin A
  作者：Robert M. Scarborough、Bruce H. Toder、Amos B. Smith

  DOI：10.1021/ja00531a037

  日期：1980.5
• PROCESS FOR THE PREPARATION OF ALKYL 1-METHYLCYCLOPROPANECARBOXYLATE
  申请人：EASTMAN CHEMICAL COMPANY

  公开号：EP1305277A2

  公开（公告）日：2003-05-02
• US6552217B2
  申请人：——

  公开号：US6552217B2

  公开（公告）日：2003-04-22
• [EN] PROCESS FOR THE PREPARATION OF ALKYL 1-METHYLCYCLOPROPANECARBOXYLATE<br/>[FR] PROCEDE DE PREPARATION DE L'ALKYL 1-METHYLCYCLOPROPANECARBOXLATE
  申请人：EASTMAN CHEM CO

  公开号：WO2002010116A2

  公开（公告）日：2002-02-07

  Disclosed is a 4-step process for the preparation of alkyl esters of 1-methylcyclopropanecarboxylic acid which comprises the steps of (1) converting η-butyrolactone to α-methyl-η-butyrolactone; (2) converting the α-methyl-η-butyrolactone from step (1) to an alkyl 4-halo-2-methyl-butyrate; (3) producing a xylene solution of the alkyl 4-halo-2-methyl-butyrate; and (4) contacting the xylene solution of the alkyl 4-halo-2-methylbutyrate from step (3) with an alkali metal alkoxide under conditions to temperature and pressure which causes vaporization of (i) an alkanol as it is fomred and (ii) an alkyl 1-methylcyclopropanecarboxylate as it si formed from the alkyl 4-halo-2-methylbutyrate. Also disclosed are processes whereby the alkyl 1-methylcyclopropanecarboxylate, prepared as described above, is converted to 1-methylcyclopropylamine.