3-重氮基-2,2-二甲基丁烷 | 65496-01-7

• 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
• 中文名称: 3-重氮基-2,2-二甲基丁烷
• 英文名称: 2-Diazo-3,3-dimethylbutan
• 英文别名: 2-Diazo-3,3-dimethylbutane；Butane, 2-diazo-3,3-dimethyl-；3-diazo-2,2-dimethylbutane
• CAS: 65496-01-7
• 化学式: C₆H₁₂N₂
• 分子量: 112.175
• InChiKey: VDGWFEICMSBRRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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-重氮基-2,2-二甲基丁烷 生成 3,3-Dimethylbutan-2-ylidene(oxido)oxidanium
  参考文献：
  名称：

  ADAM, W.;DUERR, H.;HAAS, W.;LOHRAY, B., ANGEW. CHEM., 1986, 98 ///)/HEM., N 1, 85-87

  摘要：

  DOI：
• 作为产物：
  描述：

  pinacolone hydrazone 在 mercury(II) oxide 作用下， 生成 3-重氮基-2,2-二甲基丁烷
  参考文献：
  名称：

  立体电子效应在非对映体形成的富勒烯中。

  摘要：

  研究了取代基对C（60）与各种不对称重氮烷烃反应中富勒烯非对映选择性形成的影响。对立体化学反应过程的空间需求主导了带有脂肪族和单取代pi-共振基团的重氮烷烃的非对映选择性，而同时存在的pi-共振芳族基和环丙基基团的立体电子效应在自由基中间体的闭环中起着至关重要的作用。 ，取代空间需求。

  DOI：

  10.1021/ol701789u

文献信息

• Conversions of hydrazones to diazo compounds by n-butyllithium and azidotris(diethylamino)phosphonium bromide
  作者：Mark McGuiness、Harold Shechter

  DOI：10.1016/s0040-4039(02)01443-0

  日期：2002.11

  Lithium hydrazonides, prepared by reactions of hydrazones with n-BuLi/hexane in THF at −78°C, are converted by azidotris(diethylamino)phosphonium bromide in THF at ∼0°C efficiently, rapidly, and safely to their corresponding diazo compounds along with tris(diethylamino)phosphorimine, nitrogen, and lithium bromide.

  由与正丁基锂/己烷在-78°C下于THF反应制得的酰肼锂在约0°C下于THF中由叠氮基（二乙基氨基）efficiently有效，快速，安全地转化为相应的重氮化合物与三（二乙氨基）磷亚胺，氮和溴化锂。
• Thile, Bjoern; Peatzold, Peter; Englert, Ulli, Chemische Berichte, 1992, vol. 125, p. 2681 - 2686
  作者：Thile, Bjoern、Peatzold, Peter、Englert, Ulli

  DOI：——

  日期：——
• Quast, Helmut; Kees, Frieder, Chemische Berichte, 1981, vol. 114, # 2, p. 774 - 786
  作者：Quast, Helmut、Kees, Frieder

  DOI：——

  日期：——
• Studies of thermal rearrangements of methyl 3-alkyl-3-methyl-3H-pyrazole-5-carboxylates. Concerted, stepwise, and unclassified mechanisms
  作者：Elizabeth A. Jefferson、John Warkentin

  DOI：10.1021/jo00081a028

  日期：1994.1

  Studies of the thermal rearrangements of five 3H-pyrazoles are described, in which the migrating groups were methoxymethyl, tert-butyl, 1-adamantyl, p-methoxybenzyl, and benzyl. On the basis of reaction products, rearrangement of the (methoxymethyl)pyrazole in benzene, dichloromethane, and methanol at room temperature occurs by a stepwise mechanism, involving discrete ion-pair intermediates. Observed first-order rate constants, for the rearrangement of four of the 3H-pyrazoles in benzene-d(6) and acetone-d(6) at higher temperatures, were determined The tert-butyl compound also rearranges by a stepwise mechanism in benzene d(6), acetone-d(6), and methanol-d(4) based on the fact that isobutene and tert-butyl methyl ether (in methanol) are coproducts of rearrangement. The mechanism of rearrangement of the adamantyl and methoxybenzyl systems, in both benzene d(6) and acetone-d(6) solvents, is ambiguous, the distinction between stepwise, with tight ion-pair intermediates, and concerted, with some charge separation, being unclear. However, both afforded a methyl ether in low yield during rearrangement in methanol solvent, which suggests a stepwise, ion-pair mechanism for rearrangement in that medium. No methanolysis product could be detected from the rearrangement of the benzyl compound in methanol, which suggests concerted rearrangement. Additional evidence that it rearranges by a concerted mechanism is the fact that it affords only one pyrazole product, whereas the others afford two or more.
• 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.