3-(methoxycarbonylmethyl)-1-oxaspiro<4.5>decan-2-one | 110811-05-7

• 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-(methoxycarbonylmethyl)-1-oxaspiro<4.5>decan-2-one
• 英文别名: 2-<(methoxycarbonyl)methyl>-4,4-pentamethylene-γ-butyrolactone；Methyl (2-oxo-1-oxaspiro[4.5]dec-3-yl)acetate；methyl 2-(2-oxo-1-oxaspiro[4.5]decan-3-yl)acetate
• CAS: 110811-05-7
• 化学式: C₁₂H₁₈O₄
• 分子量: 226.273
• InChiKey: WRVSBOGDHMCLCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  环己酮 在 palladium dichloride ethyl orthoacetate 、 一氧化碳 、 sodium acetate 、 copper dichloride 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 49.0h， 生成 3-(methoxycarbonylmethyl)-1-oxaspiro<4.5>decan-2-one
  参考文献：
  名称：

  Palladium(II)-catalyzed carbonylation of 3-buten-1-ols and 3-butyn-1-ols: an efficient synthesis of .gamma.-butyrolactones

  摘要：

  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).

  DOI：

  10.1021/jo00003a036

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。
• 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：——
• TAMARU YOSHINAO; HOJO MAKOTO; YOSHIDA ZEN-ICHI, TETRAHEDROM. LETT., 28,(1987) N 3, 325-328
  作者：TAMARU YOSHINAO、 HOJO MAKOTO、 YOSHIDA ZEN-ICHI

  DOI：——

  日期：——
• 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).