tert-butyl 2-(2-(tert-butoxy)-2-oxoethyl)hydrazine carboxylate | 145387-27-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl 2-(2-(tert-butoxy)-2-oxoethyl)hydrazine carboxylate
• 英文别名: tert-butyl N²-tert-butoxycarbonylhydrazinoacetate；di-tert-butyl hydrazine-1,2-dicarboxylate；t-Butyl N'-(t-Butoxycarbonylmethyl)hydrazinecarboxylate；Tert-butyl 2-[2-[(2-methylpropan-2-yl)oxycarbonyl]hydrazinyl]acetate
• CAS: 145387-27-5
• 化学式: C₁₁H₂₂N₂O₄
• 分子量: 246.307
• InChiKey: MATDIIQFJHROPT-UHFFFAOYSA-N

物化性质

• 密度：
  1.048±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-(2-(tert-butoxy)-2-oxoethyl)hydrazine carboxylate 在 三乙胺 、 sodium iodide 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 1.0h， 生成 tert-butyl N²-tert-butoxycarbonyl-N¹-iodoacetylhydrazinoacetate
  参考文献：
  名称：

  Corrie, John E. T.; Trentham, David R., Journal of the Chemical Society. Perkin transactions I, 1995, # 16, p. 1993 - 2000

  摘要：

  DOI：
• 作为产物：
  描述：

  溴乙酸叔丁酯 、 丙酮酸 在 sodium acetate 、 三乙胺 作用下， 以 乙醇 、 苯 为溶剂， 以28%的产率得到tert-butyl 2-(2-(tert-butoxy)-2-oxoethyl)hydrazine carboxylate
  参考文献：
  名称：

  Photo-labile compounds, their synthesis and use as fluorophores

  摘要：

  化合物的公式为（I），（II），其中X是可选取代的苄基，其在邻位携带一个NO.sub.2基团，Z是公式α或β的基团，R，R'和Y是可选取代的基团，R"是氢或烷基，m和n分别为1至6的整数，q为1至20的整数，以及其盐。这些基于荧光素（I）和罗丹明（II）染料的保护或笼状有机化合物可以引入生物系统中，并通过光辐射释放。例如，它们适用于用于标记蛋白质或亲脂结构。还描述了化合物的制备过程。

  公开号：

  US05434272A1

文献信息

• Examination of the Potential for Adaptive Chirality of the Nitrogen Chiral Center in Aza-Aspartame
  作者：Samir Bouayad-Gervais、William Lubell

  DOI：10.3390/molecules181214739

  日期：——

  The potential for dynamic chirality of an azapeptide nitrogen was examined by substitution of nitrogen for the α-carbon of the aspartate residue in the sweetener S,S-aspartame. Considering that S,S- and R,S-aspartame possess sweet and bitter tastes, respectively, a bitter-sweet taste of aza-aspartame 9 could be indicative of a low isomerization barrier for nitrogen chirality inter-conversion. Aza-aspartame 9 was synthesized by a combination of hydrazine and peptide chemistry. Crystallization of 9 indicated a R,S-configuration in the solid state; however, the aza-residue chiral center was considerably flattened relative to its natural amino acid counterpart. On tasting, the authors considered aza-aspartame 9 to be slightly bitter or tasteless. The lack of bitter sweet taste of aza-aspartame 9 may be due to flattening from sp2 hybridization in the urea as well as a high barrier for sp3 nitrogen inter-conversion, both of which may interfere with recognition by taste receptors.

  探讨了氮原子的动态手性可能性，方法是用氮替代甜味剂S,S-天冬氨酸残基的α-碳。考虑到S,S-和R,S-天冬氨酸分别具有甜味和苦味，氮原子手性相互转化的低异构化障碍可能使得氮-天冬氨酸9具有苦甜味。氮-天冬氨酸9通过氢肼和肽化学的结合合成。9的结晶结果表明在固态下呈现R,S-构型；然而，相较于其天然氨基酸对应物，氮残基的手性中心明显扁平化。在品尝时，作者认为氮-天冬氨酸9略微苦或无味。氮-天冬氨酸9缺乏苦甜味可能是由于脲中sp²杂化导致的扁平化，以及sp³氮转换的高障碍，这两者可能干扰味觉受体的识别。
• Total synthesis of putative montamine and a proposed structural reassignment
  作者：Lachlan M. Blair、Elizabeth A. Colby Davie、Jonathan Sperry

  DOI：10.1039/c4ob01304b

  日期：——

  The natural product montamine was originally assigned as a homodimer of moschamine linked by a N–N′ bond at the serotonin side-chain. A total synthesis of the reported structure has shown this to be incorrect. Analysis of the spectroscopic data suggests that the dimerization site has been incorrectly assigned, and montamine is likely to be a 4,4′-bismoschamine natural product previously described in

  天然产物montamine最初被指定为是通过5-羟色胺侧链上的N-N'键连接的moschamine的同型二聚体。报告的结构的全面综合显示这是不正确的。对光谱数据的分析表明，二聚化位点已被错误地分配，并且山雀胺很可能是先前文献中所述的4,4'-二苯胺氨基甲酸酯天然产物。
• Discovery of the Azaserine Biosynthetic Pathway Uncovers a Biological Route for α‐Diazoester Production
  作者：Devon Van Cura、Tai L. Ng、Jing Huang、Harry Hager、John F. Hartwig、Jay D. Keasling、Emily P. Balskus

  DOI：10.1002/anie.202304646

  日期：2023.7.10

  Discovery of the biosynthetic gene cluster for the α-diazoester natural product azaserine is reported. Isotope feeding and biochemical experiments implicate generation of a hydrazonoacetic acid intermediate that is oxidized and transferred to l-serine. This pathway represents a distinct biosynthetic strategy for diazo formation.

  据报道发现了α-重氮酯天然产物重氮丝氨酸的生物合成基因簇。同位素供给和生化实验表明亚肼基乙酸中间体的生成，该中间体被氧化并转移为L-丝氨酸。该途径代表了重氮形成的独特生物合成策略。
• Use of aminoguanidine or aminoguanidine analogs for the treatment of diseases of the nervous system
  申请人：Kaddurah-Daouk Rima

  公开号：US20070123496A1

  公开（公告）日：2007-05-31

  The present invention relates to the use of aminoguanidine compounds for treating diseases of the nervous system. Aminoguanidine compounds can be used as therapeutically effective agents against a variety of diseases of the nervous system such as diabetic and toxic neuropathies, peripheral nervous system diseases, Alzheimer's disease, Parkinson's disease, stroke, Huntington's disease, amyotropic lateral sclerosis, motor neuron disease, traumatic nerve injury, multiple sclerosis, dysmyelination and demyelination disorders, and mitochondrial diseases. The aminoguanidine compounds which can be used in the present method include (1) aminoguanidine and diaminoguanidine analogs which can act as substrates or substrate analogs for creatine kinase; (2) bisubstrate inhibitors of creatine kinase comprising covalently linked structural analogs of adenosine triphosphate (ATP) and aminoguanidine; (3) aminoguanidine analogs which can act as reversible or irreversible inhibitors of creatine kinase; and (4) N-phosphoroaminoguanidine analogs bearing nontransferable moieties which mimic the N-phosphoryl group.
• US5434272A
  申请人：——

  公开号：US5434272A

  公开（公告）日：1995-07-18