1,10-双(重氮)癸烷-2,9-二酮 | 65243-79-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1,10-双(重氮)癸烷-2,9-二酮
• 英文名称: 1,10-bis(diazo)decane-2,9-dione
• 英文别名: 1,10-Bis-diazo-decan-2,9-dion；1,10-Didiazodecane-2,9-dione
• CAS: 65243-79-0
• 化学式: C₁₀H₁₄N₄O₂
• 分子量: 222.247
• InChiKey: VQSZBWPQNPAVDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.07
• 重原子数：
  16.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  106.94
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1,10-双(重氮)癸烷-2,9-二酮 在 氢溴酸 作用下， 以 乙醚 为溶剂， 以39.5 g的产率得到1,10-dibromodecane-2,8-dione
  参考文献：
  名称：

  A New General Route to Thiophenophanes:  Synthesis and Properties of [n](2,5)Thiophenophane-1,n-diones

  摘要：

  A series of [ n]( 2,5) thiophenophane-1, n-diones ( 5) ( n = 9, 10, 12, 14, 16, and 20) were synthesized in a simple four-step route starting from the appropriate 1,omega-oligomethylenedicarboxylic acids. The bis-( halomethylketones) ( 6), which were obtained by successive treatment of the diacids with SOCl2, diazomethane, and HBr or HCl, were cyclized by Na2S under high dilution conditions. The obtained monomeric cyclic diketosulfides ( 4) were condensed with glyoxal in MeOH by slowly adding dilute NaOMe affording 5. The thiophene-2,5-dicarbonyl moiety of 5 ( n = 9) is significantly deformed as shown by X-ray crystallography, and the effect of the strain is reflected in the C=O stretching frequencies and the pi-pi* and the n-pi* absorptions.

  DOI：

  10.1021/jo060889n
• 作为产物：
  描述：

  1,8-二辛酰氯 、 三甲基硅烷化重氮甲烷 以 四氢呋喃 、 乙醚 、 乙腈 为溶剂， 反应 4.0h， 生成 1,10-双(重氮)癸烷-2,9-二酮
  参考文献：
  名称：

  催化、不对称跨环醛醇化：(+)-Hirsutene 的全合成

  摘要：

  我们报告了一种不对称的催化跨环醛醇化反应，它提供了可用于天然产物合成的多环产物。我们发现脯氨酸衍生物以良好的产率和高对映选择性催化 1,4-环辛二酮的跨环醛醇反应生成相应的环状 β-羟基酮。我们的反应的效用已在 (+)-hirustene 的全合成中得到证明。

  DOI：

  10.1021/ja8024164

文献信息

• Alkylation of benzene with α-diazoketones via cycloheptatrienyl intermediates
  作者：M. Anthony McKervey、D. Noel Russell、M. Fiona Twohig

  DOI：10.1039/c39850000491

  日期：——

  Benzyl ketones can be synthesised efficiently from benzene and α-diazoketones with sequential catalysis by rhodium(II) trifluoroacetate and trifluoroacetic acids; the process involves cycloheptatrienyl intermediates.

  可由三氟乙酸铑（II）和三氟乙酸依次催化，由苯和α-二氮酮有效地合成苄基酮。该方法涉及环庚三烯基中间体。
• The Acid Catalyzed Decomposition of Diazo Compounds. I. Synthesis of Oxazoles in the BF₃Catalyzed Reaction of Diazo Carbonyl Compounds with Nitriles
  作者：Toshikazu Ibata、Ryohei Sato

  DOI：10.1246/bcsj.52.3597

  日期：1979.12

  The BF3-catalyzed decomposition of diazo carbonyl compounds in nitriles have afforded the corresponding oxazoles in high yields. This method is applicable to diazo carbonyl compounds such as m- and p-substituted diazoacetophenones, ethyl diazoacetate, 1,2-diphenyl-2-diazoethanone, dibenzoyldiazomethane, and dimethyl diazomalonate. Bis(diazo ketone)s such as terminal bis(diazoacetylated) alkanes (III1−4:

  BF3 催化的腈中重氮羰基化合物的分解以高产率提供了相应的恶唑。该方法适用于间位和对位取代的重氮苯乙酮、重氮乙酸乙酯、1,2-二苯基-2-重氮乙酮、二苯甲酰重氮甲烷和重氮丙二酸二甲酯等重氮羰基化合物。双（重氮酮）如末端双（重氮乙酰化）烷烃（III1-4：n=6, 8, 10, 12）和间和对双（重氮乙酰基）苯也在类似的反应中得到相应的双恶唑。该反应被解释为通过甜菜碱中间体的逐步机制，由 对重氮羰基化合物的羰基氧的攻击引发。描述了恶唑的发射光谱。
• Synthesis of macrocyclic oxo-crown ethers from αω-bis-diazo-ketones and polyethylene glycols
  作者：Sunanta Kulkowit、M. Anthony McKervey

  DOI：10.1039/c39810000616

  日期：——

  Derivatives of macrocyclic crown ethers in which two ethereal oxygen atoms have been replaced by carbonyl groups have been synthesised by the bis-(acetylacetonato) copper-catalysed cyclisation of αω-bis-diazo-ketones with polyethylene glycols; three such oxo-crown ethers complex with potassium ion in chloroform.

  其中两个醚氧原子已被取代的羰基的大环冠醚的衍生物已经由双- （乙酰丙酮）α的铜催化的环化合成ω -双重氮基酮与聚乙二醇; 三个这样的氧代冠醚与钾离子在氯仿中形成络合物。
• Fahr,E., Justus Liebigs Annalen der Chemie, 1960, vol. 638, p. 1 - 32
  作者：Fahr,E.

  DOI：——

  日期：——
• Canonica; Bacchetti, Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1951, vol. <8>10, p. 479,484
  作者：Canonica、Bacchetti

  DOI：——

  日期：——