2-<(methoxycarbonyl)methyl>-γ-butyrolactone | 54405-62-8

• 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: 2-<(methoxycarbonyl)methyl>-γ-butyrolactone
• 英文别名: γ-butyrolactone 2-acetic acid methyl ester；2-(methoxycarbonylmethyl)-4-butanolide；methyl 2-oxotetrahydrofuran-3-acetate；3-Furanacetic acid, tetrahydro-2-oxo-, methyl ester；methyl 2-(2-oxooxolan-3-yl)acetate
• CAS: 54405-62-8
• 化学式: C₇H₁₀O₄
• 分子量: 158.154
• InChiKey: ULOWAAFIHMAPLX-UHFFFAOYSA-N

物化性质

• 沸点：
  276.2±13.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  11
• 可旋转键数：
  3
• 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：

  (+/-)-2-methoxyhexahydrofuro[2,3-b]furan 在 三氟化硼乙醚 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以87%的产率得到2-<(methoxycarbonyl)methyl>-γ-butyrolactone
  参考文献：
  名称：

  Malanga, Corrado; Mannucci, Serena; Lardicci, Luciano, Journal of Chemical Research - Part S, 2001, # 3, p. 97 - 99

  摘要：

  DOI：

文献信息

• Selective Mono- and Bis(alkoxycarbonylation)s of Olefins Catalyzed by Palladium in the Presence of Cu(I) or Cu(II) Chloride under Remarkably Mild Conditions. Application to the Synthesis of γ-Butyrolactone Derivatives
  作者：Shiho Toda、Masanori Miyamoto、Hideki Kinoshita、Katsuhiko Inomata

  DOI：10.1246/bcsj.64.3600

  日期：1991.12

  Palladium-catalyzed mono- and bis(alkoxycarbonylation)s of olefins were controlled by the use of copper(II) and copper(1) chloride, respectively, in alcohol under normal pressure of carbon monoxide and oxygen at room temperature without any other additives. 3-Buten-1-ols gave the corresponding γ-butyrolactones and 2-oxotetrahydrofuran-3-acetic acid esters, respectively, in high yields.

  在室温下、正常压力的二氧化碳和氧气环境下，使用铜(II)和铜(I)氯化物分别控制钯催化的单和双(烷氧基羰基化)反应，无需其他添加剂即可使烯烃产生反应。3-丁烯-1-醇则分别高效地生成相应的γ-丁酰内酯和2-氧杂四氢呋喃-3-乙酸酯。
• Development of Thiourea-Based Ligands for the Palladium-Catalyzed Bis(methoxycarbonylation) of Terminal Olefins
  作者：Mingji Dai、Cuihua Wang、Guangbin Dong、Jing Xiang、Tuoping Luo、Bo Liang、Jiahua Chen、Zhen Yang

  DOI：10.1002/ejoc.200300543

  日期：2003.11

  Thiourea-based ligands were evaluated for the palladium-catalyzed bis(methoxycarbonylation) of terminal olefins. The usefulness of these ligands for this reaction is demonstrated by their stability to oxidizing agents, and their superiority in preventing palladium precipitation and double-bond isomerization. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

  对基于硫脲的配体进行钯催化的末端烯烃双（甲氧基羰基化）的评价。这些配体对氧化剂的稳定性以及在防止钯沉淀和双键异构化方面的优越性证明了这些配体在该反应中的有用性。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• Palladium(II)-catalyzed carbonylation of 3-buten-1-ols and 3-butyn-1-ols: an efficient synthesis of .gamma.-butyrolactones
  作者：Yoshinao Tamaru、Makoto Hojo、Zenichi Yoshida

  DOI：10.1021/jo00003a036

  日期：1991.2

  Palladium(II)-catalyzed dicarbonylation of 3-buten-1-ols (1) in the presence of propylene oxide and ethyl orthoacetate in methanol-dichloromethane under carbon monoxide at atmospheric pressure afforded alpha-[(methoxycarbonyl)methyl]-gamma-butyrolactones (2) in good yields. This dicarbonylation reaction occurs via stereospecific cis addition. Under similar conditions, 4-(trimethylsilyl)-3-butyn-1-ols (4a and 4b) undergo dicarbonylation to provide cis-dicarbonylated alpha-methylene-gamma-butyrolactones (5a and 5b, respectively). 4-Alkyl-and 4-aryl-3-butyn-1-ols (4c-g), on the other hand, undergo trans alkoxycarbonylation across the triple bond and selectively furnish E tetrasubstituted alpha-methylene-gamma-butyrolactones (6).
• Inter- and intramolecular di-alkoxycarbonylation of 3-butenols catalyzed by palladium(II)
  作者：Yoshinao Tamaru、Makoto Hojo、Zen-ichi Yoshida

  DOI：10.1016/s0040-4039(00)95719-8

  日期：——
• TAMARU, YOSHINAO;HOJO, MAKOTO;YOSHIDA, ZEN-ICHI, J. ORG. CHEM., 56,(1991) N, C. 1099-1105
  作者：TAMARU, YOSHINAO、HOJO, MAKOTO、YOSHIDA, ZEN-ICHI

  DOI：——

  日期：——