(E)-(1-(13)C)1-bromo-4-phenyl-but-3-en-2-one | 1005481-98-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-(1-(13)C)1-bromo-4-phenyl-but-3-en-2-one
• CAS: 1005481-98-0
• 化学式: C₁₀H₉BrO
• 分子量: 226.074
• InChiKey: LDEBGMOZLPUFEE-JTIUWLFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.66
• 重原子数：
  12.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (E)-(1-(13)C)1-bromo-4-phenyl-but-3-en-2-one 在 silver carbonate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 0.33h， 生成
  参考文献：
  名称：

  Synthesis of 13C-Dehydrocoelenterazine and NMR Studies on the Bioluminescence of a Symplectoteuthis Model

  摘要：

  The bioluminescence of luminous squid (Symplectoteuthis oualaniensis) is presumed to be initiated by the addition of the sulfhydryl residue of a photoprotein to dehydrocoelenterazine (DCL). To clarify this step, a novel synthetic route was established to label DCL with C-13. Dithiothreitol (DTT) and glutathione (GSH) were used as photoprotein models. The addition of DTT and GSH to C-13-labeled DCL gave luminous chromophores. Its structures were confirmed by NMR and MS spectrometry. The DTT adduct emitted light under alkaline condition to produce an oxidized compound. Thus we succeeded in modeling the bioluminescence of a photoprotein with DTT. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00163-0
• 作为产物：
  描述：

  (E)-4-phenyl-2-(trimethylsiloxy)but-3-enenitrile 在 硫酸 、 水 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 生成 (E)-(1-(13)C)1-bromo-4-phenyl-but-3-en-2-one
  参考文献：
  名称：

  Synthesis of 13C-Dehydrocoelenterazine and NMR Studies on the Bioluminescence of a Symplectoteuthis Model

  摘要：

  The bioluminescence of luminous squid (Symplectoteuthis oualaniensis) is presumed to be initiated by the addition of the sulfhydryl residue of a photoprotein to dehydrocoelenterazine (DCL). To clarify this step, a novel synthetic route was established to label DCL with C-13. Dithiothreitol (DTT) and glutathione (GSH) were used as photoprotein models. The addition of DTT and GSH to C-13-labeled DCL gave luminous chromophores. Its structures were confirmed by NMR and MS spectrometry. The DTT adduct emitted light under alkaline condition to produce an oxidized compound. Thus we succeeded in modeling the bioluminescence of a photoprotein with DTT. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00163-0

文献信息

• Efficient Control of π-Alkyne and Vinylidene Complex Pathways for the W(CO)₅(L)-Catalyzed Synthesis of Two Types of Nitrogen-Containing Bicyclic Compounds
  作者：Yuji Onizawa、Hiroyuki Kusama、Nobuharu Iwasawa

  DOI：10.1021/ja0782605

  日期：2008.1.1

  2-azabicyclo[3.3.0]octanes were obtained in good yield via pi-alkyne complexes. On the other hand, treatment of the same substrates with a catalytic amount of W(CO)6 in the presence of n-Bu3N under the same reaction conditions gave 3-azabicyclo[3.3.0]octanes in good yield exclusively via vinylidene complexes. Thus, the pi-alkyne and vinylidene complex pathways are easily controlled by using a catalytic amount

  当在系链中含有 NMs 部分的 omega-炔二烯醇甲硅烷基醚在光照射下用催化量的 W(CO)6 处理​​时，2-氮杂双环 [3.3.0] 辛烷通过 pi-炔配合物以良好的产率获得。另一方面，在相同反应条件下，在 n-Bu3N 存在下用催化量的 W(CO)6 处理​​相同的底物，仅通过亚乙烯基配合物以良好的产率得到 3-氮杂双环 [3.3.0] 辛烷。因此，通过使用催化量的 W(CO)5(L) 和胺，可以轻松控制 pi-炔烃和亚乙烯基络合物途径。
• Synthesis of 13C-dehydrocoelenterazine and model studies on Symplectoteuthis squid bioluminescence
  作者：Minoru Isobe、Masaki Kuse、Yoshio Yasuda、Hiroyuki Takahashi

  DOI：10.1016/s0960-894x(98)00525-3

  日期：1998.10

  to its apoprotein. To prove this mechanism, we have established new synthetic route to ca. 100%-13C incorporated dehydrocoelenterazine and coelenterazine at the neighboring carbon of the 2-position of 2,3-dihydroimidazo-[1,2a]-pyrazinone skeleton. This 13C enriched dehydrocoelenterazine readily converted in equilibrium between its adduct forms as a diastereomixture with glutathione (GSH) or dithiothreitol

  在冲绳乌贼Symplectoteuthis oualaniensis L的鱿鱼生物发光的光蛋白中，脱氢腔肠素已被指定为其脱辅基蛋白的发色前体。为了证明这种机制，我们建立了新的合成途径。100％-13C在2，3-二氢咪唑基-[1,2a]-吡嗪酮骨架的2-位的相邻碳上结合了脱氢腔肠素和腔肠素。这种富含13C的脱氢腔肠素很容易在其加合物形式之间平衡转化为与具有巯基的谷胱甘肽（GSH）或二硫苏糖醇（DTT）化合物的非对映混合物。这类加合物的结构在酸性条件下固定，然后通过NMR光谱以及吸光度和荧光光谱进行讨论。