2-(3-methyl-2,5-dioxopyrrolidin-1-yl)benzoic acid | 114911-16-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(3-methyl-2,5-dioxopyrrolidin-1-yl)benzoic acid
• CAS: 114911-16-9
• 化学式: C₁₂H₁₁NO₄
• 分子量: 233.224
• InChiKey: OMRMFMYVQMSRLZ-UHFFFAOYSA-N

物化性质

• 熔点：
  150-154 °C(Solv: acetone (67-64-1); hexane (110-54-3))
• 沸点：
  507.0±33.0 °C(Predicted)
• 密度：
  1.376±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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-(3-methyl-2,5-dioxopyrrolidin-1-yl)benzoic acid 、 pyridin-3-ylmethyl methanesulfonate 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 Pyridin-3-ylmethyl 2-(3-methyl-2,5-dioxopyrrolidin-1-yl)benzoate
  参考文献：
  名称：

  A direct connection of a tricyclic analog of methyllycaconitine with 2-methylsuccinimidobenzoic acid

  摘要：

  An efficient procedure for attaching the methylsuccinimidobenzoate ester unit to an ABE ring segment of methyllycaconitine is described. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00239-1
• 作为产物：
  描述：

  2-(3-methyl-2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)benzoic acid 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以98%的产率得到2-(3-methyl-2,5-dioxopyrrolidin-1-yl)benzoic acid
  参考文献：
  名称：

  Barker, David; Brimble, Margaret A.; McLeod, Malcolm D., Synthesis, 2003, # 5, p. 656 - 658

  摘要：

  DOI：

文献信息

• The synthesis of 5-substituted ring E analogs of methyllycaconitine via the Suzuki–Miyaura cross-coupling reaction
  作者：Junfeng Huang、Crina M. Orac、Susan McKay、Dennis B. McKay、Stephen C. Bergmeier

  DOI：10.1016/j.bmc.2008.01.050

  日期：2008.4.1

  analogs of methyllycaconitine were prepared and evaluated in nicotinic acetylcholine receptor binding assays. The desired analogs were prepared through the Suzuki-Miyaura cross-coupling reaction of methyl 5-bromo-nicotinate. The Suzuki-Miyaura cross-coupling reactions of pyridines with electron withdrawing substituents have not been extensively described previously.

  制备了新的3，5-二取代的甲基lycaconitine E环类似物，并在烟碱乙酰胆碱受体结合试验中进行了评估。通过5-溴烟酸甲酯的Suzuki-Miyaura交叉偶联反应制备所需的类似物。吡啶与吸电子取代基的Suzuki-Miyaura交叉偶联反应以前没有被广泛描述。
• Baillie, Lynn C.; Bearder, John R.; Li, Wang-Shi, Journal of the Chemical Society. Perkin transactions I, 1998, # 24, p. 4047 - 4055
  作者：Baillie, Lynn C.、Bearder, John R.、Li, Wang-Shi、Sherringham, John A.、Whiting, Donald A.

  DOI：——

  日期：——
• Ring E analogs of methyllycaconitine (MLA) as novel nicotinic antagonists
  作者：Stephen C. Bergmeier、David J. Lapinsky、R.Benjamin Free、Dennis B McKay

  DOI：10.1016/s0960-894x(99)00378-9

  日期：1999.8

  We have prepared ring E analogs of the diterpenoid alkaloid methyllycaconitine. These compounds have been assayed for nicotinic activity and were found to act as functional antagonists on adrenal nicotinic receptors. (C) 1999 Elsevier Science Ltd. All rights reserved.