4-ethoxy-4-[3-(2,4-dinitrophenyldisulfanyl)phenyl]spiro(1,2-dioxetane-3,2'-tricyclo[3.3.1.1^3,7]decane)

• 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: 4-ethoxy-4-[3-(2,4-dinitrophenyldisulfanyl)phenyl]spiro(1,2-dioxetane-3,2'-tricyclo[3.3.1.1^3,7]decane)
• 英文别名: 3'-[3-[(2,4-Dinitrophenyl)disulfanyl]phenyl]-3'-ethoxyspiro[adamantane-2,4'-dioxetane]
• 化学式: C₂₅H₂₆N₂O₇S₂
• 分子量: 530.623
• InChiKey: FIDINSOFPKYGRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  170
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  金刚烷酮 在 亚磷酸三苯酯 、 lithium aluminium tetrahydride 、 titanium(III) chloride 、 臭氧 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 4-ethoxy-4-[3-(2,4-dinitrophenyldisulfanyl)phenyl]spiro(1,2-dioxetane-3,2'-tricyclo[3.3.1.1^3,7]decane)
  参考文献：
  名称：

  酯和酮之间的麦克默里分子间交叉偶联：范围和局限性

  摘要：

  在关于合成用于检测硫醇的带有二氧杂环丁烷的化学发光探针的研究过程中，我们面临着位阻苄基烯醇醚的合成。通过使用酯和酮之间的分子间McMurry交叉偶联解决了这个问题。在本文中，连同化学发光探针的合成，讨论了这种低价钛基碳碳双键形成的范围和局限性。

  DOI：

  10.1016/s0040-4039(02)00617-2

文献信息

• McMurry intermolecular cross-coupling between an ester and a ketone: scope and limitations
  作者：Stéphane Sabelle、Jérôme Hydrio、Eric Leclerc、Charles Mioskowski、Pierre-Yves Renard

  DOI：10.1016/s0040-4039(02)00617-2

  日期：2002.5

  were faced with the synthesis of sterically hindered benzylic enol ethers. This issue was solved via the use of an intermolecular McMurry cross-coupling between an ester and a ketone. In this article, together with the synthesis of the chemiluminescent probe, the scope and limitations of this low valent titanium based carboncarbon double bond formation are discussed.

  在关于合成用于检测硫醇的带有二氧杂环丁烷的化学发光探针的研究过程中，我们面临着位阻苄基烯醇醚的合成。通过使用酯和酮之间的分子间McMurry交叉偶联解决了这个问题。在本文中，连同化学发光探针的合成，讨论了这种低价钛基碳碳双键形成的范围和局限性。
• Design and Synthesis of Chemiluminescent Probes for the Detection of Cholinesterase Activity
  作者：Stéphane Sabelle、Pierre-Yves Renard、Karine Pecorella、Sophie de Suzzoni-Dézard、Christophe Créminon、Jacques Grassi、Charles Mioskowski

  DOI：10.1021/ja0171299

  日期：2002.5.1

  Acetylcholinesterase is one of the most widely used and studied enzymes. Not only does this enzyme regulate neurotransmission (and thus play a key role in neurodegenerative processes) but it is also a prime target for pest control agents and warfare agents. Above all, due to its particularly high turnover rate, acetylcholinesterase is among the most efficient reporter enzymes yet described (for use as enzymatic tracer in immunoassays, for instance), However, its activity is detected through a colorimetric reagent, the Ellman reagent, which displays low detection limits and is often subject to background perturbations. In the course of our search for a more sensitive detection assay, we describe here a first-generation 1,2-dioxetane chemiluminescent probe, based on chemically induced electron exchange luminescence, which has an approximately 10 times lower detection limit than the Ellman colorimetric assay (2.5 x 10(-19) mol for Electrophorus electricus AChE in its tetrameric form).