N,N-dimethylhydroxylamine | 5725-96-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N-dimethylhydroxylamine
• CAS: 5725-96-2
• 化学式: C₂H₇NO
• mdl: MFCD06654504
• 分子量: 61.0837
• InChiKey: VMESOKCXSYNAKD-UHFFFAOYSA-N

物化性质

• 熔点：
  98-101 °C
• 沸点：
  97.91°C (rough estimate)
• 密度：
  0.8904 (rough estimate)
• 蒸汽压力：
  21.17 mmHg

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  4
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-dimethylhydroxylamine 在 正丁基锂 、 二氯硅烷 作用下， 生成 (N,N-dimethylhydroxylamino)chlorosilane
  参考文献：
  名称：

  β-Donor Interactions of Exceptional Strength in N,N-Dimethylhydroxylaminochlorosilane, ClH₂SiONMe₂

  摘要：

  The compounds ClH2SiONMe2 and ClH2SiONEt2 have been prepared by the reaction of the corresponding O-lithiated hydroxylamines and dichlorosilane. Their identity has been proved by gas-phase IR and solution NMR (H-1, C-13, N-15, O-17, and Si-29) spectroscopy. In contrast to CM2SiONMe2, ClH2SiONEt2 is unstable at ambient temperature and decomposes to give H2SiCl2 and H2Si(ONEt2)(2). ClH2SiONEt2 shows dynamic behavior in the solution as shown by low-temperature NMR. In the crystal ClH2SiONMe2 (low-temperature crystallography) is present as anti-conformer (torsional angle Cl-Si-O-N 180 degrees) and shows an exceptionally small Si-O-N angle of 79.7(1)degrees and a Si ... N distance of 2.028(1) Angstrom, corresponding to a relatively strong Si-N-beta-donor interaction. Ab initio calculations predict a wider Si-O-N angle of 91.6 degrees (MP2/6-311G**). A gas-phase structure determination by electron diffraction shows the presence of two conformers (anti and gauche), which are equal in potential energy. The Si-O-N angle in the anti-conformer is 87.1(9)degrees and that in the gauche-conformer 104.7(11)degrees [Cl-Si-O-N torsion angle: 72.9(28)degrees]. Calculations (MP2/6-31G*) have shown the angle Si-O-N and the energy of the system to be largely dependent on the torsion angle Cl-Si-O-N, with a variation of the angle Si-O-N over a range of 30 degrees during a full rotation of Cl-Si-O-N. Analysis of the calculated charges on the Si and N atoms show the beta-donor interaction not to be simply caused by electrostatic interaction. Natural bond orbital analysis describes a Ip-N --> sigma(Si-X)* type negative hyperconjugation as an important contribution to beta-donor bonding. The silicon substituent in anti position to nitrogen exerts the major effect on the strength of the beta-donor bond. Simultaneous analysis of negative hyperconjugation Ip-O --> sigma(Si-X)* shows the Si-O-N compounds to have similar contributions to this interaction as H3SiOCH3 and questions negative hyperconjugation to be quoted in isolation for the rationalization of the wide bond angles in silyl ethers.

  DOI：

  10.1021/ja980933j
• 作为产物：
  描述：

  N,N-二甲基环己胺 生成 N,N-dimethylhydroxylamine
  参考文献：
  名称：

  1260.氨基酸和肽。第二十四部分。1-羟基哌啶的酯和其他NN-二烷基羟胺的酯在肽合成中的用途以及作为选择性酰化剂的用途

  摘要：

  DOI：

  10.1039/jr9650006814
• 作为试剂：
  描述：

  zinc(II) nitrate hexahydrate 、 4-[(phosphonomethylamino)-methyl]benzoic acid 在 N,N-dimethylhydroxylamine 作用下， 以 水 为溶剂， 反应 72.0h， 以68%的产率得到Zn(4-[(phosphonomethylamino)-methyl]benzoic acid (-2H))
  参考文献：
  名称：

  呈弱铁磁性的配体几何定向极性钴（II）膦酸酯

  摘要：

  4-[（膦酰基甲基氨基）甲基]苯甲酸（H 3 L）与M（NO 3）2（M = Co，Zn）的水热反应提供了两种金属膦酸酯，即Co（HL）和Zn（HL）。它们都显示3D极性柱状分层结构。磁测量结果证实Co（HL）在约2 K处表现出倾斜的反铁磁有序。在低温下，弱的铁磁成分归因于极性非中心对称晶体结构引起的Dzyaloshinskii-Moriya（DM）相互作用。Zn II化合物的二次谐波产生（SHG）响应约为磷酸二氢钾（KDP）的0.2倍。

  DOI：

  10.1021/cg301542n

文献信息

• Plant Growth Regulator Daminozide Is a Selective Inhibitor of Human KDM2/7 Histone Demethylases
  作者：Nathan R. Rose、Esther C. Y. Woon、Anthony Tumber、Louise J. Walport、Rasheduzzaman Chowdhury、Xuan Shirley Li、Oliver N. F. King、Clarisse Lejeune、Stanley S. Ng、Tobias Krojer、Mun Chiang Chan、Anna M. Rydzik、Richard J. Hopkinson、Ka Hing Che、Michelle Daniel、Claire Strain-Damerell、Carina Gileadi、Grazyna Kochan、Ivanhoe K. H. Leung、James Dunford、Kar Kheng Yeoh、Peter J. Ratcliffe、Nicola Burgess-Brown、Frank von Delft、Susanne Muller、Brian Marsden、Paul E. Brennan、Michael A. McDonough、Udo Oppermann、Robert J. Klose、Christopher J. Schofield、Akane Kawamura

  DOI：10.1021/jm300677j

  日期：2012.7.26

  N-demethylation of Nε-methyl lysine residues in histones and are current therapeutic targets. A set of human 2-oxoglutarate analogues were screened using a unified assay platform for JmjC demethylases and related oxygenases. Results led to the finding that daminozide (N-(dimethylamino)succinamic acid, 160 Da), a plant growth regulator, selectively inhibits the KDM2/7 JmjC subfamily. Kinetic and crystallographic

  的JmjC结构氧酶催化Ñ的-demethylation Ñ ε -甲基赖氨酸残基在组蛋白和是当前治疗靶标。使用 JmjC 脱甲基酶和相关加氧酶的统一检测平台筛选了一组人 2-酮戊二酸类似物。结果导致发现 daminozide（N-（二甲氨基）琥珀酸，160 Da），一种植物生长调节剂，选择性抑制 KDM2/7 JmjC 亚家族。动力学和晶体学研究表明，daminozide 通过其酰肼羰基和二甲氨基与活性位点金属螯合。
• Different modes of aggregation in organoaluminium and -gallium hydroxylamides
  作者：Norbert W. Mitzel、Christian Lustig、Markus Woski

  DOI：10.1039/b311781b

  日期：——

  The organoaluminium and -gallium hydroxylamides (Me2GaONMe2)2, (tBu2AlONMe2)2, (tBu2GaONMe2)2 and (Me2AlONiPr2)2 have been prepared by the reaction of the hydroxylamines Me2NOH and iPr2NOH with the trialkylmetal compounds trimethylgallium, tri-tbutylaluminium and tri-tbutylgallium, respectively. All compounds have been characterised by NMR spectroscopy (1H, 13C, 15N, 17O and 27Al), by mass spectrometry and elemental analyses. The crystal structures of the four compounds have been determined, showing that they all form dimers but with different modes of aggregation: (Me2GaONMe2)2 has a Ga2O2N2 six-membered ring, (tBu2AlONMe2)2 and (Me2AlONiPr2)2 have Al2O2 four-membered rings, (tBu2GaONMe2)2 forms a Ga2O2N five-membered ring.

  通过羟胺Me2NOH和iPr2NOH分别与三甲基镓、三叔丁基铝和三叔丁基镓反应，制备了有机铝和镓的羟胺盐(Me2GaONMe2)2、(tBu2AlONMe2)2、(tBu2GaONMe2)2和(Me2AlONiPr2)2。所有化合物均通过NMR光谱（1H、13C、15N、17O和27Al）、质谱和元素分析进行了表征。四个化合物的晶体结构已经确定，显示它们都以二聚体形式存在，但聚集模式不同：(Me2GaONMe2)2具有六元环Ga2O2N2，(tBu2AlONMe2)2和(Me2AlONiPr2)2具有四元环Al2O2，而(tBu2GaONMe2)2则形成五元环Ga2O2N。
• 1-(Aminoalkyl)-6-aryl-4H-s-triazolo[4,3-a][1,4]benzodiazepines with antianxiety and antidepressant activity
  作者：Jackson B. Hester、Allan D. Rudzik、Philip F. Von Voigtlander

  DOI：10.1021/jm00178a009

  日期：1980.4

  A series of 1-(aminoalkyl)-6-aryl-4H-s-triazolo[4,3-a][1,4]benzodiazepines has been prepared and evaluated for central nervous system activity. We have found that members of this series have activity in pharmacological test systems designed to detect both anxiolytic and antidepressant activity. Each type of activity could be varied independently by appropriate substituent selections.

  已经制备了一系列的1-（氨基烷基）-6-芳基-4H-s-三唑并[4，3-a] [1，4]苯并二氮杂并评估中枢神经系统活性。我们发现该系列的成员在旨在检测抗焦虑和抗抑郁活性的药理学测试系统中具有活性。每种类型的活性可以通过适当的取代基选择独立地变化。
• [EN] MORPHOLINE DERIVATIVES AS NOREPINEPHRINE REUPTAKE INHIBITORS<br/>[FR] DERIVES DE MORPHOLINE UTILISES COMME INHIBITEURS DU RECAPTAGE DE LA NOREPINEPHRINE
  申请人：LILLY CO ELI

  公开号：WO2005047272A1

  公开（公告）日：2005-05-26

  Compounds of the general formula (I) are inhibitors of the reuptake of norepinephrine. As such, they may be useful for the treatment of disorders of the central and/or peripheral nervous system.

  通式（I）的化合物是去甲肾上腺素再摄取抑制剂。因此，它们可能对中枢神经系统和/或外周神经系统的疾病治疗有用。
• Synthesis of Unexpected Bifunctionalized Thiazoles by Nucleophilic Attack on Allenyl Isothiocyanate
  作者：Baker Jawabrah Al-Hourani、Frank Richter、Kai Vrobel、Klaus Banert、Marcus Korb、Tobias Rüffer、Bernhard Walfort、Heinrich Lang

  DOI：10.1002/ejoc.201301851

  日期：2014.5

  reactivity is also seen with N-aminophthalimide. In the presence of azide salt, hydrazoic acid, or N,N-disubstituted hydroxylamines, however, allenyl isothiocyanate is converted into bifunctionalized thiazoles. We explain the formation of these products by nucleophilic addition at the isothiocyanato moiety followed by ring closure and an N–N or N–O cleavage reaction to generate short-lived 2-imino-5-methylidenethiazole

  用各种亲核试剂处理异硫氰酸丙二烯酯会产生在 2 位具有官能团的 5-甲基噻唑。N-氨基邻苯二甲酰亚胺也观察到相同的反应模式。然而，在叠氮化物盐、偶氮酸或 N,N-二取代羟胺的存在下，异硫氰酸烯丙酯被转化为双官能化的噻唑。我们通过在异硫氰酸基部分亲核加成，然后闭环和 N-N 或 N-O 裂解反应来生成短寿命的 2-imino-5-methylidenethiazole 或 5-methylidenethiazol-2-one 来解释这些产物的形成。这些中间体通过加成反应被捕获以得到最终的杂环化合物。在 N,N-二取代羟胺的情况下，

表征谱图