3-Diazopentane | 61111-70-4

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 炔丙基型1，3-偶极有机化合物
• 英文名称: 3-Diazopentane
• 英文别名: diethyldiazomethane
• CAS: 61111-70-4
• 化学式: C₅H₁₀N₂
• 分子量: 98.1478
• InChiKey: DPNQVRUILKQZTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-Diazopentane 、 3,4-dichlorocyclobut-1-ene 以45%的产率得到
  参考文献：
  名称：

  ELIBRACHT P.; DAHLER P., LIEBIGS ANN. CHEM., 1979, NO 11, 1890-1907

  摘要：

  DOI：
• 作为产物：
  描述：

  diethylketone hydrazone 在 lead(IV) acetate 、 1,1,2,3-四甲基胍 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以77%的产率得到3-Diazopentane
  参考文献：
  名称：

  Advantageous Syntheses of Diazo Compounds by Oxidation of Hydrazones with Lead Tetraacetate in Basic Environments

  摘要：

  Varied sensitive diazo compounds 3 are produced efficiently and safely in 3-6 g quantities by oxidation (eq 1) of hydrazones 1 at -78 degrees C with lead tetraacetate (2) in triethylamine/chloroform, N-methylmorpholine/dimethylformamide, tetramethylguanidine (8)/dimethylformamide, and tetramethylguanidine/methylene chloride, respectively, upon use of appropriate workup and handling techniques. New and improved nonhazardous procedures have been developed for preparing and handling hydrazones 1 from aldehydes and ketones in reactions with excess hydrazine.

  DOI：

  10.1021/jo00120a013

文献信息

• Amino-Substituted Butatrienes: Unusual η¹ Ligands Formed by an Unusual Reaction
  作者：Bernhard Reichmann、Matthias Drexler、Bernhard Weibert、Normen Szesni、Tobias Strittmatter、Helmut Fischer

  DOI：10.1021/om101163j

  日期：2011.3.14

  ═C═C(R′)2}], are isolated from the reaction of diazoalkanes (R′)2C−N2 (R′ = Me, Et, nPr) with alkoxy(amino)allenylidene complexes [(CO)5M═C═C═C(NMe2)OR] (M = Cr, W; R = Me, Et, (−)-menthyl) or with the (alkylthio)(amino)allenylidene complex [(CO)5W═C═C═C(NMe2)SnPr]. These new η1-butatriene complexes are related to Cα phosphine adducts of allenylidene complexes such as [(CO)5WC(PMe3)═C═C(NMe2)Ph}]

  双反应（氨基）allenylidene配合物[（CO）5 W═C═C═C（NME 2）2 ]与diethyldiazomethane产生两个产品，环状卡宾络合物（2）由1,2-加成的Et 2 C-N 2到C α -C β的allenylidene配体和η的键1 -butatriene配合物[（CO）5 W C [C（NME 2）2 ]═C═CEt 2 }]（3）。复数2会慢慢消除N 2并重新排列为3。相比之下，只有η 1-重氮三烯配合物[（CO）5 M C [C（C（NMe 2）XR]═C═C（R'）2 }]从重氮烷烃（R'）2 C-N 2（R '= ME等，ñ PR）与烷氧基（氨基）allenylidene配合物[（CO）5 M═C═C═C（NME 2）OR]（M =铬，W; R =甲基，乙基，（ - ） -薄荷基）或与（烷硫基）（氨基）allenylidene配合物[（CO）5 W═C═C═C（NME
• Addition of diazoalkanes to alkyne(pentacarbonyl)–chromium and –tungsten—formation of 3H-pyrazole complexes
  作者：Mokhles M. Abd-Elzaher、Bernhard Weibert、Helmut Fischer

  DOI：10.1016/s0022-328x(02)02163-0

  日期：2003.3

  Photolysis of [M(CO)6] (M=Cr, W) in CH2Cl2 at −78 °C generates [(CO)5M(CH2Cl2)]. Subsequent sequential reaction of [(CO)5M(CH2Cl2)] with terminal alkynes, HCCR (R=COOMe, Ph, p-Tol), and diazoalkanes, R1(R2)CN2 (R1=Me, Et, Ph; R2=Me, Et) affords 3H-pyrazole complexes, [(CO)5M–(R1)(R2)]. These complexes are derived from addition of diazoalkanes to alkyne complex intermediates, [(CO)5M(HCCR)]. Their

  在-78°C下在CH 2 Cl 2中对[M（CO）6 ]（M = Cr，W）进行光解会生成[（CO）5 M（CH 2 Cl 2）]。[[CO）5 M（CH 2 Cl 2）]与末端炔烃HCCR（R = COOMe，Ph，p- Tol）和重氮烷烃R 1（R 2）CN 2（R 1）的后续顺序反应= Me，Et，Ph; R 2 = Me，Et）得到3 H-吡唑配合物，[（CO）5 M– （R 1）（R 2）]。这些配合物是通过将重氮烷烃添加到炔烃配合物中间体[（CO）5 M（HCCR）]中获得的。其互变异构体亚乙烯基，[（CO）5 MCC（R）H]，存在于与该炔络合物平衡溶液，不发生反应。同样地，二取代的可分离的亚乙烯基络合物，[（CO）5 MCC（R“）R *]，不添加重氮烷。
• Advantageous Syntheses of Diazo Compounds by Oxidation of Hydrazones with Lead Tetraacetate in Basic Environments
  作者：Terrence L. Holton、Harold Schechter

  DOI：10.1021/jo00120a013

  日期：1995.7

  Varied sensitive diazo compounds 3 are produced efficiently and safely in 3-6 g quantities by oxidation (eq 1) of hydrazones 1 at -78 degrees C with lead tetraacetate (2) in triethylamine/chloroform, N-methylmorpholine/dimethylformamide, tetramethylguanidine (8)/dimethylformamide, and tetramethylguanidine/methylene chloride, respectively, upon use of appropriate workup and handling techniques. New and improved nonhazardous procedures have been developed for preparing and handling hydrazones 1 from aldehydes and ketones in reactions with excess hydrazine.
• ELIBRACHT P.; DAHLER P., LIEBIGS ANN. CHEM., 1979, NO 11, 1890-1907
  作者：ELIBRACHT P.、 DAHLER P.

  DOI：——

  日期：——