3,3'-dinitrobibenzyl | 19829-61-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 3,3'-dinitrobibenzyl
• 英文别名: 1-Nitro-3-[2-(3-nitrophenyl)ethyl]benzene
• CAS: 19829-61-9
• 化学式: C₁₄H₁₂N₂O₄
• 分子量: 272.26
• InChiKey: PMQWUZNZVKKYNS-UHFFFAOYSA-N

物化性质

• 沸点：
  430.0±25.0 °C(Predicted)
• 密度：
  1.317±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  91.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-硝基溴苄 在 cobalt,triphenylphosphane,chloride 作用下， 以 乙酸乙酯 、 苯 为溶剂， 以50%的产率得到3,3'-dinitrobibenzyl
  参考文献：
  名称：

  Aromatic aldehydes from benzylbromides via Cobalt(I) mediated benzyl radicals in the presence of aerial oxygen: a mild oxidation reaction in neutral condition

  摘要：

  Co(PPh3)(3)Cl has been shown to be a novel mediator Tor the conversion of benzylic bromides to aromatic aldehydes under mild conditions in the presence of aerial oxygen probably via benzylic radicals. In the absence of oxygen, the carbon-carbon coupling reactions bale been utilised to afford a series of functionalised benzylic dimers. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00110-5

文献信息

• Structure and mechanism in the photo-retro-aldol type reactions of nitrobenzyl derivatives. Photochemical heterolytic cleavage of carbon-carbon bonds
  作者：Peter. Wan、S. Muralidharan

  DOI：10.1021/ja00221a038

  日期：1988.6

  Photolyse d'aryl-2 propanols-1 en phase aqueuse et en phase oxygenee; obtention de toluenes, de bibenzyles et d'hydroperoxy benzenes respectivement. Etude du mecanisme de photoretroaldolisation par un effet isotopique

  光解 d'aryl-2 propanols-1 en phase aqueuse et en phase oxygenee; 分别获得甲苯、双苄和氢过氧苯。光逆醛醇化的机械练习曲
• Photochemistry of α-aryl carbonyl compounds in aqueous solution
  作者：Peter Wan、Keith Yates

  DOI：10.1039/c39820000275

  日期：——

  Irradiation of the α-aryl carbonyl compounds (1)–(4) with u.v. light in aqueous solution gave different results from those observed in organic solvents.

  在水溶液中用紫外光照射α-芳基羰基化合物（1）–（4）得出的结果与在有机溶剂中观察到的结果不同。
• Substituent Effects on the Photocleavage of Benzyl−Sulfur Bonds. Observation of the “<i>Meta</i> Effect”
  作者：Steven A. Fleming、Anton W. Jensen

  DOI：10.1021/jo9606923

  日期：1996.1.1

  substituted benzyl phenyl sulide. The effect of oxygen on quantum yields is best observed after samples are thoroughly outgassed with consecutive freeze-pump-thaw cycles. It is shown that oxygen diminishes the substituent effect. Upon photolysis of the outgassed samples, the meta-substituted derivatives showed more significant variances than the para derivatives. The meta derivatives are most efficiently

  苄基苯基硫醚已用于研究苄基硫键的光解机理。四个实验表明反应通过自由基中间体。首先，所观察到的光产物都可以通过自由基机理得到证明。第二，自由基中间体被五己烯基系链捕获。第三，对4-NO（2）衍生物类似物的紫外分析表明没有激基复合物或电子转移途径。第四，未观察到σ值与量子产率之间因取代的苄基苯基硫化物的损失而产生的强相关性。样品在连续的冷冻-泵-解冻循环中彻底除气后，最好观察到氧气对量子产率的影响。结果表明，氧减弱了取代作用。对脱气样品进行光解后，与对位衍生物相比，间位取代衍生物表现出更大的变化。间衍生物最有效地按以下顺序裂解：3-CN> 3-NO（2）> 3-CF（3）> 3-CH（3）> 3-OCH（3）。这些发现可以通过增加3-OCH（3）衍生物的ipso基团的电子密度到形成苄基的自由基和减少3-CN衍生物的ipso基团的电子密度到形成苄基基团来证明。
• Tomioka, Hideo; Tabayashi, Kazuo; Izava, Yasuji, Journal of the Chemical Society. Chemical communications, 1985, # 13, p. 906 - 907
  作者：Tomioka, Hideo、Tabayashi, Kazuo、Izava, Yasuji

  DOI：——

  日期：——
• Photocleavage of benzyl-sulfide bonds
  作者：Steven A. Fleming、Anton W. Jensen

  DOI：10.1021/jo00077a041

  日期：1993.12

  The nucleoside transport inhihitor 6-[(4-nitrobenzyl)thio]-9-(beta-D-ribofuranosyl)purine, NBMPR, has been used successfully in photoaffinity labeling. We have studied the mechanism for photocleavage of the benzyl-sulfur bond by using substituted benzyl phenyl sulfides as analogues of NBMPR. This has enabled us to enhance the photoreactivity of the benzyl-sulfur bond. We have also performed ,,radical clock'' studies with a hexenyl side chain to trap reactive intermediates. The mechanistic interpretation from the substituent and side chain studies is that the benzyl-sulfur moiety is photocleaved via a homolytic pathway.