2-(tetrachloro-phthalimido)-3-methyl-butanoic acid | 69926-17-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(tetrachloro-phthalimido)-3-methyl-butanoic acid
• 英文别名: 3-methyl-2-(4,5,6,7-tetrachloro-1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)butanoic acid；3-methyl-2-(4,5,6,7-tetrachloro-1,3-dioxoisoindol-2-yl)butanoic acid
• CAS: 69926-17-6
• 化学式: C₁₃H₉Cl₄NO₄
• 分子量: 385.031
• InChiKey: KPBIRKYPIXGNJM-UHFFFAOYSA-N

物化性质

• 沸点：
  564.4±50.0 °C(Predicted)
• 密度：
  1.670±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  74.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(tetrachloro-phthalimido)-3-methyl-butanoic acid 在 4-二甲氨基吡啶 、 acetyl hypobromite 、 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 14.0h， 生成
  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
• 作为产物：
  描述：

  苯酐 、 alkaline earth salt of/the/ methylsulfuric acid 在 cast iron 氯 作用下， 以 溶剂黄146 为溶剂， 反应 6.5h， 生成 2-(tetrachloro-phthalimido)-3-methyl-butanoic acid
  参考文献：
  名称：

  El-Naggar; Zaher; El-Basiouny, Farmaco, Edizione Scientifica, 1984, vol. 39, # 2, p. 154 - 161

  摘要：

  DOI：

文献信息

• 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.
• El-Naggar; Zaher; El-Basiouny, Farmaco, Edizione Scientifica, 1984, vol. 39, # 2, p. 154 - 161
  作者：El-Naggar、Zaher、El-Basiouny、Khalaf

  DOI：——

  日期：——