5,5'-(ethane-1,2-diyl)bis(dihydrofuran-2(3H)-one) | 58936-17-7

• 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: 5,5'-(ethane-1,2-diyl)bis(dihydrofuran-2(3H)-one)
• 英文别名: 1,2-bis-(5-oxo-tetrahydro-[2]furyl)-ethane；1,2-Bis-(5-oxo-tetrahydro-[2]furyl)-aethan；5,5'-(Ethane-1,2-diyl)di(oxolan-2-one)；5-[2-(5-oxooxolan-2-yl)ethyl]oxolan-2-one
• CAS: 58936-17-7
• 化学式: C₁₀H₁₄O₄
• 分子量: 198.219
• InChiKey: WXTRDPUBGCPUCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,5'-(ethane-1,2-diyl)bis(dihydrofuran-2(3H)-one) 在 1,4-二氧六环 、 copper oxide-chromium oxide 作用下， 250.0 ℃ 、11.18 MPa 条件下， 生成 2,5-Bis-(3-hydroxy-propyl)-tetrahydro-furan
  参考文献：
  名称：

  Hayashi, Kogyo Kagaku zasshi / Journal of the Society of Chemical Industry, 1957, vol. 60, p. 282,285

  摘要：

  DOI：
• 作为产物：
  描述：

  癸二酸 在 4-二甲氨基吡啶 、 acetyl hypobromite 、 四溴化碳 、 silver(I) acetate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 34.42h， 生成 5,5'-(ethane-1,2-diyl)bis(dihydrofuran-2(3H)-one)
  参考文献：
  名称：

  Synthesis of Lactones via C–H Functionalization of Nonactivated C(sp³)–H Bonds

  摘要：

  An electron-deficient amide is utilized as a directing group to functionalize nonactivated C(sp(3))-H bonds through radical 1,5-hydrogen abstraction. The gamma-bromoamides formed are subsequently converted to gamma-lactones under mild conditions. The method described is not limited to tertiary and secondary positions but also allows functionalization of primary nonactivated sp(3)-hybridized positions in a one-pot sequence. In addition, the broad functional group tolerance renders this method suitable for the late-stage introduction of gamma-lactones into complex carbon frameworks.

  DOI：

  10.1021/acs.orglett.6b03371

文献信息

• Hayashi; Iwakura, Nippon Kagaku Zasshi, 1958, vol. 79, p. 1134,1137
  作者：Hayashi、Iwakura

  DOI：——

  日期：——
• Synthesis of Lactones via C–H Functionalization of Nonactivated C(sp³)–H Bonds
  作者：Johannes Richers、Michael Heilmann、Markus Drees、Konrad Tiefenbacher

  DOI：10.1021/acs.orglett.6b03371

  日期：2016.12.16

  An electron-deficient amide is utilized as a directing group to functionalize nonactivated C(sp(3))-H bonds through radical 1,5-hydrogen abstraction. The gamma-bromoamides formed are subsequently converted to gamma-lactones under mild conditions. The method described is not limited to tertiary and secondary positions but also allows functionalization of primary nonactivated sp(3)-hybridized positions in a one-pot sequence. In addition, the broad functional group tolerance renders this method suitable for the late-stage introduction of gamma-lactones into complex carbon frameworks.
• Hayashi, Kogyo Kagaku zasshi / Journal of the Society of Chemical Industry, 1957, vol. 60, p. 282,285
  作者：Hayashi

  DOI：——

  日期：——