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2-methyl-3-(diethoxyphosphorylmethyl)furan | 153649-83-3

中文名称
——
中文别名
——
英文名称
2-methyl-3-(diethoxyphosphorylmethyl)furan
英文别名
3-(Diethoxyphosphorylmethyl)-2-methylfuran
2-methyl-3-(diethoxyphosphorylmethyl)furan化学式
CAS
153649-83-3
化学式
C10H17O4P
mdl
——
分子量
232.216
InChiKey
GIHMKICZRKICAL-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    1.2
  • 重原子数:
    15
  • 可旋转键数:
    6
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.6
  • 拓扑面积:
    48.7
  • 氢给体数:
    0
  • 氢受体数:
    4

SDS

SDS:32c622718902f8ffc4a994d300a57b5b
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上下游信息

  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    2-methyl-3-(diethoxyphosphorylmethyl)furan吡啶 作用下, 以 氯仿 为溶剂, 生成 2-methyl-5-bromo-3-(diethoxyphosphorylmethyl)furan
    参考文献:
    名称:
    Synthesis of isomeric bromo(diethoxyphosphorylmethyl)furans
    摘要:
    Series of the previously unknown bromo(diethoxyphosphorylmethyl)furans including four of six possible regioisomers is synthesized. The target products were obtained by bromination of the corresponding (diethoxyphosphorylmethyl)furans or by a four-step synthesis including bromination of isomeric methyl-furancarboxylates, reduction of the products formed to the corresponding alcohols, substitution of hydroxy group with halogen and phosphorylation by the Michaelis-Becker reaction. It was established for the first fime that in the course of bromination of alkyl carboxylates and phosphonates of the furan series under the typical conditions of electrophilic reaction (Br(2) + 10% molar of AlCl(3), chloroform) the substituent enters not only into the heteroring, but also into the side chain. In the case of 5-methyl-2-(diethoxyphosphorylmethyl)furan only the last reaction pathway is observed. It is shown that bromo(chloromethyl)furans react with sodium diethyl phosphite not only according to the Michaelis-Becker scheme leading to phosphonates, but also by the pathway of debromination of the furan ring. The last unexpected reaction may acquire a practical use for removing a substituent protecting the alpha-position of the furan ring under mild conditions.
    DOI:
    10.1134/s1070363209030050
  • 作为产物:
    描述:
    2-methyl-5-bromo-3-(chloromethyl)furan 、 sodium diethyl phosphite 为溶剂, 反应 16.0h, 以16%的产率得到3-(氯甲基)-2-甲基呋喃
    参考文献:
    名称:
    Synthesis of isomeric bromo(diethoxyphosphorylmethyl)furans
    摘要:
    Series of the previously unknown bromo(diethoxyphosphorylmethyl)furans including four of six possible regioisomers is synthesized. The target products were obtained by bromination of the corresponding (diethoxyphosphorylmethyl)furans or by a four-step synthesis including bromination of isomeric methyl-furancarboxylates, reduction of the products formed to the corresponding alcohols, substitution of hydroxy group with halogen and phosphorylation by the Michaelis-Becker reaction. It was established for the first fime that in the course of bromination of alkyl carboxylates and phosphonates of the furan series under the typical conditions of electrophilic reaction (Br(2) + 10% molar of AlCl(3), chloroform) the substituent enters not only into the heteroring, but also into the side chain. In the case of 5-methyl-2-(diethoxyphosphorylmethyl)furan only the last reaction pathway is observed. It is shown that bromo(chloromethyl)furans react with sodium diethyl phosphite not only according to the Michaelis-Becker scheme leading to phosphonates, but also by the pathway of debromination of the furan ring. The last unexpected reaction may acquire a practical use for removing a substituent protecting the alpha-position of the furan ring under mild conditions.
    DOI:
    10.1134/s1070363209030050
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文献信息

  • Pevzner; Ignat'ev; Ionin, Russian Journal of General Chemistry, 1997, vol. 67, # 2, p. 224 - 226
    作者:Pevzner、Ignat'ev、Ionin
    DOI:——
    日期:——
  • Aminomethylation of 2- and 3-(Diethoxyphosphorylmethyl)furans
    作者:L. M. Pevzner
    DOI:10.1023/b:rugc.0000039082.14939.56
    日期:2004.5
    Dimethyl(methylene)ammonium chloride reacts with 2- and 3-(diethoxyphosphorylmethyl)furans by the free alpha position of the furan ring to give the corresponding aminomethyl derivatives. 2,5-Disubstituted furans do not enter this reaction.
  • Pevzner, L. M.; Ignat'ev, V. M.; Ionin, B. I., Russian Journal of General Chemistry, 1993, vol. 63, # 7.2, p. 1101 - 1105
    作者:Pevzner, L. M.、Ignat'ev, V. M.、Ionin, B. I.
    DOI:——
    日期:——
  • Synthesis of isomeric bromo(diethoxyphosphorylmethyl)furans
    作者:L. M. Pevzner
    DOI:10.1134/s1070363209030050
    日期:2009.3
    Series of the previously unknown bromo(diethoxyphosphorylmethyl)furans including four of six possible regioisomers is synthesized. The target products were obtained by bromination of the corresponding (diethoxyphosphorylmethyl)furans or by a four-step synthesis including bromination of isomeric methyl-furancarboxylates, reduction of the products formed to the corresponding alcohols, substitution of hydroxy group with halogen and phosphorylation by the Michaelis-Becker reaction. It was established for the first fime that in the course of bromination of alkyl carboxylates and phosphonates of the furan series under the typical conditions of electrophilic reaction (Br(2) + 10% molar of AlCl(3), chloroform) the substituent enters not only into the heteroring, but also into the side chain. In the case of 5-methyl-2-(diethoxyphosphorylmethyl)furan only the last reaction pathway is observed. It is shown that bromo(chloromethyl)furans react with sodium diethyl phosphite not only according to the Michaelis-Becker scheme leading to phosphonates, but also by the pathway of debromination of the furan ring. The last unexpected reaction may acquire a practical use for removing a substituent protecting the alpha-position of the furan ring under mild conditions.
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