3,3-二甲基环丙烷-1,1,2,2-四甲腈 | 13017-67-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 3,3-二甲基环丙烷-1,1,2,2-四甲腈
• 英文名称: 3,3-dimethylcyclopropane-1,1,2,2-tetracarbonitrile
• 英文别名: 1,1,2,2-Cyclopropanetetracarbonitrile, 3,3-dimethyl-
• CAS: 13017-67-9
• 化学式: C₉H₆N₄
• 分子量: 170.173
• InChiKey: JIEYOKFTSKQLLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  95.2
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  3,3-二甲基环丙烷-1,1,2,2-四甲腈 在 alkaline aqueous KOBr 作用下， 生成 6,6-dimethyl-2,4-dioxo-3-aza-bicyclo[3.1.0]hexane-1,5-dicarbonitrile
  参考文献：
  名称：

  Ramberg; Wideqvist, Arkiv foer Kemi, 1941, vol. 14 B, # 37, p. 4,11, 12

  摘要：

  DOI：
• 作为产物：
  描述：

  2-溴丙二腈 在 丙酮 、 potassium iodide 作用下， 生成 3,3-二甲基环丙烷-1,1,2,2-四甲腈
  参考文献：
  名称：

  Paramagnetic contribution of serum iron to the spin-spin relaxation rate (1/T 2) measured by MRI

  摘要：

  Spin-spin relaxation time T-2 values of serum with and without iron were measured by magnetic resonance imaging (MRI) to find the proton relaxivity of Fe(III) in serum. T-2 values in serum containing definite amounts of added iron were also measured before and after addition of ascorbic acid. The difference in the 1/T-2 of serum with and without ascorbic acid was used for recalculation of the added iron values, Recalculated iron values confirm that the difference in healthy serum is caused by iron only. In addition, in order to find the paramagnetic contribution of serum iron, T-2 values of iron-deficient, healthy and iron-overloaded serum were measured before and after addition of ascorbic acid. The difference in the 1/T-2 values was then applied to the calculation of the serum iron values. The consistency of iron values determined from the difference to those by autoanalyzer suggests that the differences in diseased serum also represent the paramagnetic contribution of serum iron. The data imply that serum iron content in healthy, iron-deficient and iron-overloaded serum may be assessed by MRI.

  DOI：

  10.1007/bf03170519

文献信息

• Electrochemical Transformation of Malononitrile and Carbonyl Compounds into Functionally Substituted Cyclopropanes: Electrocatalytic Variant of the Wideqvist Reaction
  作者：Michail N. Elinson、Sergey K. Feducovich、Tatiana L. Lizunova、Gennady I. Nikishin

  DOI：10.1016/s0040-4020(00)00195-2

  日期：2000.5

  Electrolysis of malononitrile and carbonyl compounds in the presence of alkali metal halides in an undivided cell results in the formation of substituted 1,1,2,2-tetracyanocyclopropanes in 60–90% yield. This electrocatalytic variant of the Wideqvist reaction using malononitrile instead of bromomalonitrile was successfully performed. Electrocatalytic transformation of substituted 1,1,2,2-tetracyanocyclopropanes

  在不分开的电解槽中，在碱金属卤化物存在下，丙二腈和羰基化合物的电解导致取代的1,1,2,2-四氰基环丙烷的形成，产率为60-90％。使用丙二腈代替溴丙二腈成功进行了Wideqvist反应的这种电催化变体。在未分开的电池中，甲醇或乙醇中取代的1,1,2,2-四氰基环丙烷的电催化转化导致取代的2-氨基-4,4-二烷氧基-1,5-二氰基-3-氮杂双环[3.1.0] hex-通过0.05-0.10 F / mol的电量后，二烯的产率为70-95％。
• One-pot cascade assembling of 3-substituted tetracyanocyclopropanes from alkylidenemalononitriles and malononitrile by the only bromine direct action
  作者：Anatolii N. Vereshchagin、Michail N. Elinson、Nikita O. Stepanov、Gennady I. Nikishin

  DOI：10.1016/j.mencom.2009.11.010

  日期：2009.11

  The new cascade reaction was found: the formation of cyclopropanes from alkylidenemalononitriles and malononitrile by the only bromine direct action; the action of aqueous bromine on the equal amounts of alkylidenemalononitriles and malononitrile in EtOH–H 2 O solutions results in the formation of 3-substituted 1,1,2,2-tetracyanocyclopropanes in 55–98% yields.

  发现了新的级联反应：仅通过溴的直接作用，由亚烷基丙二腈和丙二腈形成环丙烷。在EtOH–H 2 O溶液中溴水溶液对等量的亚烷基丙二腈和丙二腈的作用导致形成3–取代的1,1,2,2-四氰基环丙烷，产率为55–98％。
• Observations of tetrel bonding between sp³-carbon and THF
  作者：Victoria L. Heywood、Thomas P. J. Alford、Julius J. Roeleveld、Siebe J. Lekanne Deprez、Abraham Verhoofstad、Jarl Ivar van der Vlugt、Sérgio R. Domingos、Melanie Schnell、Anthony P. Davis、Tiddo J. Mooibroek

  DOI：10.1039/d0sc01559h

  日期：——

  report the direct observation of tetrel bonding interactions between sp3-carbons of the supramolecular synthon 3,3-dimethyl-tetracyanocyclopropane (1) and tetrahydrofuran in the gas and crystalline phase. The intermolecular contact is established via σ-holes and is driven mainly by electrostatic forces. The complex manifests distinct binding geometries when captured in the crystalline phase and in the

  我们报告了在气相和结晶相中超分子合成子3,3-二甲基-四氰基环丙烷（1）的sp 3-碳与四氢呋喃之间的锡特尔键相互作用的直接观察。分子间接触是通过σ孔建立的，并且主要由静电力驱动。当在结晶相和气相中捕获时，该复合物表现出独特的结合几何形状。我们使用互补气相量子化学计算阐明了这些结合趋势，发现加合物的总结合能为-11.2 kcal mol -1。我们的观察为超分子化学中以sp 3 -C为中心的非共价键结合方案的新策略铺平了道路。
• Cycloadditions of `Thiocarbonyl Ylides' with Tetracyanoethylene (=Ethenetetracarbonitrile): Interception of Intermediates
  作者：Rolf Huisgen、Grzegorz Mloston、Elke Langhals

  DOI：10.1002/1522-2675(20010613)84:6<1805::aid-hlca1805>3.0.co;2-t

  日期：2001.6.13

  Thiocarbonyl ylides (=sulfonium ylides) belong to the most nucleophilic 1,3-dipoles (high HO energy). In their reactions with tetracyanoethylene (TCNE=ethenetetracarbonitrile; low LU energy), a borderline crossing from the concerted mechanism to a two-step pathway via a 1,5-zwitterion was observed. Steric hindrance at one or both termini of the 1,3-dipole is an additional requirement. The ylides 3

  硫代羰基叶立德（=锍叶立德）属于最亲核的 1,3-偶极子（高 H2O 能量）。在它们与四氰基乙烯（TCNE=乙烯四甲腈；低 LU 能量）的反应中，观察到从协同机制到通过 1,5-两性离子的两步途径的边界交叉。1,3-偶极子的一个或两个末端的空间位阻是附加要求。叶立德 3 和 13 通过 N2 消除二氢-1,3,4-噻二唑而释放，经历电环化或 1,4-H 位移。叶立德 3 和 13 是碱基并提供不同区域化学的 MeOH 加合物。而 3 和 TCNE 在 abs。45° 的 THF 提供了 (3+2) 环加合物 20，THF 中 0.5 – 5 vol-% 的 MeOH 含量以 65:35 的比例产生了七元内酰胺醚 22 和硫杂环戊烷 20（方案 4）。水 (0. 5 – 1 vol-%) 在 THF 中以相同的比例生成内酰胺 24 和加合物 20。假定为第一个中间体的两性离子 26 进入竞争反应：对硫杂环戊烷
• Reactions of a Tetrasubstituted Thiocarbonyl Ylide; New Evidence for Two-Step Cycloadditions
  作者：Rolf Huisgen、Grzegorz Mloston

  DOI：10.3987/com-89-s40

  日期：——