(2-methoxyphenyl)diazomethane | 82988-73-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2-methoxyphenyl)diazomethane
• 英文别名: 1-(Diazomethyl)-2-methoxybenzene
• CAS: 82988-73-6
• 化学式: C₈H₈N₂O
• 分子量: 148.164
• InChiKey: WEALKZRBSKLLCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  11.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2-methoxyphenyl)diazomethane 以 二氯甲烷 、 正戊烷 为溶剂， 生成 Cl2Ru(=CH-o-OMeC6H4)(PCy3)
  参考文献：
  名称：

  A Recyclable Ru-Based Metathesis Catalyst

  摘要：

  A Ru carbene (8, Scheme 2) that contains an internal metal-oxygen chelate is an active metathesis catalyst and is readily obtained by the sequential treatment of Cl2Ru(PPh3)(3) with (2-isopropoxyphenyl)-diazomethane and PCy3. This Ru-carbene complex offers excellent stability to air and moisture and can be recycled in high yield by silica gel column chromatography. The structures of this and related complexes have been unambiguously established by NMR and single-crystal X-ray diffraction studies.

  DOI：

  10.1021/ja983222u
• 作为产物：
  描述：

  2-methoxybenzaldehyde tosylhydrazone 在 四甲基胍 作用下， 反应 0.5h， 以58%的产率得到(2-methoxyphenyl)diazomethane
  参考文献：
  名称：

  A Recyclable Ru-Based Metathesis Catalyst

  摘要：

  A Ru carbene (8, Scheme 2) that contains an internal metal-oxygen chelate is an active metathesis catalyst and is readily obtained by the sequential treatment of Cl2Ru(PPh3)(3) with (2-isopropoxyphenyl)-diazomethane and PCy3. This Ru-carbene complex offers excellent stability to air and moisture and can be recycled in high yield by silica gel column chromatography. The structures of this and related complexes have been unambiguously established by NMR and single-crystal X-ray diffraction studies.

  DOI：

  10.1021/ja983222u

文献信息

• Rhodium ion catalyzed decomposition of aryldiazoalkanes
  作者：B.K.Ravi Shankar、Harold Shechter

  DOI：10.1016/s0040-4039(00)87320-7

  日期：1982.1

  Aryldiazomethanes are converted by rhodium(II) acetate and iodorhodium(III) tetraphenylporphyrin to cis- rather than trans-1,2-diarylethylenes. Secondary aryldiazoalkanes react with rhodirum(II) acetate to give azines.

  芳族重氮甲烷被乙酸铑（II）和异碘鎓（III）四苯基卟啉转化为顺式而不是反式1，2-二芳基乙烯。仲芳基重氮烷与乙酸Rhodirum（II）反应生成杂志。
• Cyclopropanation using flow-generated diazo compounds
  作者：Nuria M. Roda、Duc N. Tran、Claudio Battilocchio、Ricardo Labes、Richard J. Ingham、Joel M. Hawkins、Steven V. Ley

  DOI：10.1039/c5ob00019j

  日期：——

  A practical and mild protocol for the cyclopropanation of unstabilised diazo compounds is reported.

  一种实用且温和的方法用于环丙烷化不稳定的重氮化合物。
• N−N Bond Cleavage in Diazoalkanes by a Bis(imino)pyridine Iron Complex
  作者：Sarah K. Russell、Emil Lobkovsky、Paul J. Chirik

  DOI：10.1021/ja8075132

  日期：2009.1.14

  Addition of monosubstituted diazoalkanes, N(2)CHR (R = Ph, p-Tolyl, (t)Bu, Cy), to the bis(imino)pyridine iron dinitrogen complex, ((iPr)PDI)Fe(N(2))(2), at 23 degrees C in benzene-d(6) resulted in rapid cleavage of the N-N bond to yield the iron nitrile and imine complexes, ((iPr)PDI)FeNCR and ((iPr)PDI)FeHNCHR, respectively. Aryl azines were also cleaved with ((iPr)PDI)Fe(N(2))(2) and yielded the

  将单取代重氮烷烃 N(2)CHR (R = Ph, p-Tolyl, (t)Bu, Cy) 添加到双 (亚氨基) 吡啶铁二氮络合物 ((iPr)PDI)Fe(N(2) )(2)，在 23 摄氏度的苯-d(6) 中导致 NN 键快速裂解，分别产生铁腈和亚胺配合物 ((iPr)PDI)FeNCR 和 ((iPr)PDI)FeHNCHR . 芳基吖嗪也被 ((iPr)PDI)Fe(N(2))(2) 裂解并产生相同的产物。机理研究支持这样一种途径，即首先形成亚烷基亚铁，然后与另一当量的重氮烷快速 [4pi + 2pi] 环加成。随后确定速率的 1,3-氢迁移，然后是逆环加成产生观察到的产物。
• An Enantioselective Synthesis of 2-Aryl Cycloalkanones by Sc-Catalyzed Carbon Insertion
  作者：Victor L. Rendina、David C. Moebius、Jason S. Kingsbury

  DOI：10.1021/ol200402m

  日期：2011.4.15

  Current methods for asymmetric alpha-arylation require blocking groups to prevent reaction at the alpha'-carbon, basic conditions that promote racemization, or multistep synthesis. This work records the first catalytic enantioselective examples of the diazoalkane-carbonyl homologation reaction. Medium ring 2-aryl ketones are prepared in one step in up to 98:2 er and 99% yield from the unsubstituted lower homologue by Sc-catalyzed aryldiazomethyl insertion with simple bis- and tris(oxazoline) ligands.
• Mohammed; Gohar; Abdel-Latif, Pharmazie, 1985, vol. 40, # 5, p. 312 - 314
  作者：Mohammed、Gohar、Abdel-Latif、Badr

  DOI：——

  日期：——