ethyl 1-iodopropyl-2-oxocyclopentanoate | 122898-06-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 1-iodopropyl-2-oxocyclopentanoate
• 英文别名: ethyl 1-(3-iodopropyl)-2-oxocyclopentanecarboxylate；Ethyl 1-(3-iodopropyl)-2-oxocyclopentane-1-carboxylate
• CAS: 122898-06-0
• 化学式: C₁₁H₁₇IO₃
• 分子量: 324.159
• InChiKey: KDXJAFFHTCIVMD-UHFFFAOYSA-N

物化性质

• 沸点：
  352.9±27.0 °C(Predicted)
• 密度：
  1.538±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 1-iodopropyl-2-oxocyclopentanoate 在 六甲基磷酰三胺 、 lithium aluminium tetrahydride 、 samarium diiodide 、 lithium amide 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (3aSR,6aRS)-6a-(aminomethyl)hexahydropentalen-3a(1H)-ol
  参考文献：
  名称：

  Discovery of non-zwitterionic aryl sulfonamides as Nav1.7 inhibitors with efficacy in preclinical behavioral models and translational measures of nociceptive neuron activation

  摘要：

  Since zwitterionic benzenesulfonamide Na(v)1.7 inhibitors suffer from poor membrane permeability, we sought to eliminate this characteristic by replacing the basic moiety with non-basic bicyclic acetals and monocyclic ethers. These efforts led to the discovery of the non-zwitterionic aryl sulfonamide 49 as a selective Na(v)1.7 inhibitor with improved membrane permeability. Despite its moderate cellular activity, 49 exhibited robust efficacy in mouse models of neuropathic and inflammatory pain and modulated translational electromyogram measures associated with activation of nociceptive neurons. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.08.012
• 作为产物：
  描述：

  1,3-二碘丙烷 、 2-氧代环戊羧酸乙酯 在 六甲基磷酰三胺 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以24%的产率得到ethyl 1-iodopropyl-2-oxocyclopentanoate
  参考文献：
  名称：

  新型的自由基环扩环反应

  摘要：

  描述了卤代烷基β-酮酯的新颖的自由基引发的环膨胀。用适当的二卤化物将β-酮酯烷基化后，将所得的卤化物用氢化三正丁基锡进行回流处理。平稳地重排成均相的γ-酮酯。提出了一种氧自由基中间体用于该反应。

  DOI：

  10.1016/0040-4020(89)80035-3

文献信息

• Novel free radical ring-expansion reactions
  作者：Paul Dowd、Soo-Chang Choi

  DOI：10.1016/0040-4020(89)80035-3

  日期：1989.1

  A novel free radical initiated ring expansion of haloalkyl β-keto esters is described. Following alkylation of the β-keto ester with the appropriate dihalide, the resulting halide is treated at reflux with tri-n-butyltin hydride. Rearrangement to the homologated γ-keto ester occurs smoothly. An oxy radical intermediate is proposed for the reaction.

  描述了卤代烷基β-酮酯的新颖的自由基引发的环膨胀。用适当的二卤化物将β-酮酯烷基化后，将所得的卤化物用氢化三正丁基锡进行回流处理。平稳地重排成均相的γ-酮酯。提出了一种氧自由基中间体用于该反应。
• DOWD, PAUL;CHOI, SOO-CHANG, TETRAHEDRON, 45,(1989) N, C. 77-90
  作者：DOWD, PAUL、CHOI, SOO-CHANG

  DOI：——

  日期：——
• Discovery of non-zwitterionic aryl sulfonamides as Nav1.7 inhibitors with efficacy in preclinical behavioral models and translational measures of nociceptive neuron activation
  作者：Yong-Jin Wu、Jason Guernon、Andrea McClure、Guanglin Luo、Ramkumar Rajamani、Alicia Ng、Amy Easton、Amy Newton、Clotilde Bourin、Dawn Parker、Kathleen Mosure、Omar Barnaby、Matthew G. Soars、Ronald J. Knox、Michele Matchett、Rick Pieschl、James Herrington、Ping Chen、D.V. Sivarao、Linda J. Bristow、Nicholas A. Meanwell、Joanne Bronson、Richard Olson、Lorin A. Thompson、Carolyn Dzierba

  DOI：10.1016/j.bmc.2017.08.012

  日期：2017.10

  Since zwitterionic benzenesulfonamide Na(v)1.7 inhibitors suffer from poor membrane permeability, we sought to eliminate this characteristic by replacing the basic moiety with non-basic bicyclic acetals and monocyclic ethers. These efforts led to the discovery of the non-zwitterionic aryl sulfonamide 49 as a selective Na(v)1.7 inhibitor with improved membrane permeability. Despite its moderate cellular activity, 49 exhibited robust efficacy in mouse models of neuropathic and inflammatory pain and modulated translational electromyogram measures associated with activation of nociceptive neurons. (C) 2017 Elsevier Ltd. All rights reserved.