(3E)-3-羟基亚胺-2,2-二甲基丙烷-1-醇 | 36559-87-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: (3E)-3-羟基亚胺-2,2-二甲基丙烷-1-醇
• 英文名称: 3-hydroxy-2,2-dimethylpropionaldoxime
• 英文别名: 3-hydroxy-2,2-dimethylpropanal oxime；3-hydroxy-2,2-dimethyl-propionaldehyde oxime；3-Hydroxy-2.2-dimethyl-propionaldoxim；3-Hydroxy-2,2-dimethyl-propionaldehyd-oxim；2.2-Dimethyl-propanol-(3)-oxim-(1)；Form-isobutyr-aldol-oxim；Propanal, 3-hydroxy-2,2-dimethyl-, oxime；3-hydroxyimino-2,2-dimethylpropan-1-ol
• CAS: 36559-87-2
• 化学式: C₅H₁₁NO₂
• 分子量: 117.148
• InChiKey: ZIIOSFHXHLTBRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  8
• 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：
  52.8
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  (3E)-3-羟基亚胺-2,2-二甲基丙烷-1-醇 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 3-氰基-3-甲基丁酰氯
  参考文献：
  名称：

  Kern,J.M.; Federli,P., Bulletin de la Societe Chimique de France, 1972, p. 4379 - 4383

  摘要：

  DOI：
• 作为产物：
  描述：

  2,2-二甲基-3-羟基丙醛 在 盐酸羟胺 、 水 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以71%的产率得到(3E)-3-羟基亚胺-2,2-二甲基丙烷-1-醇
  参考文献：
  名称：

  固相合成RNA序列中核糖核苷2'-羟基保护基的2-氰基-2-2,2-二甲基乙胺基-N-氧甲基

  摘要：

  2-氰基-2-甲基丙醛与2'- O-氨氧基甲基核糖核苷的反应可产生稳定且可逆的2' - O-（2-氰基-2-2,2-二甲基乙胺-N-氧甲基）核糖核苷。在对核碱基进行N-保护，5'-二甲氧基三苯甲基化和3'-磷酸化之后，得到的2'-保护的核糖核苷亚磷酰胺单体被用于三个嵌合RNA序列的固相合成，每个序列的嘌呤/嘧啶比率不同。在5‐苄硫基‐1 H存在下进行亚磷酰胺单体的活化时-四唑，在180 s内平均获得99％的耦合效率。RNA链装配完成后，在标准碱性条件下进行核苷酸碱基和磷酸盐保护基的去除以及从固相支持物中释放序列，而2' - O-（2-氰基-2，通过用氟化四正丁基铵（0.5  m）处理可实现2-二甲基乙胺基-N-氧甲基）保护基（不释放RNA烷基化副产物）在干燥的DMSO中于55°C下放置24–48 h。通过聚丙烯酰胺凝胶电泳（PAGE），酶水解和基质辅助激光解吸/电离（MALDI）质谱对完全

  DOI：

  10.1002/chem.201204235

文献信息

• Nitrones and oximes of bifunctional carbonyl compounds and their reaction products with diarylborinic acids. Crystal and molecular structure of examples of five-, six-, and seven-membered boron chelates
  作者：Wolfgang Kliegel、Gottfried Lubkowitz、Jens O Pokriefke、Steven J Rettig、James Trotter

  DOI：10.1139/v00-137

  日期：2000.10.1

  Synthesis has been carried out of diarylboron chelates of 2- and 3-hydroxynitrones, of 2- and 3-hydroxyoximes, and of 2-carboxynitrones and a 2-carboxyoxime. The structures have been determined from spectroscopic data and from X-ray analyses of 5d, 9a, 11b, and 19. Crystals (at 180 K) of 5d are monoclinic, a = 10.543(2), b = 19.085(4), c = 10.2667(3) Å, β = 90.4978(7)°, Z = 4, space group P2₁/c; those of 9a are orthorhombic, a = 10.9913(5), b = 14.9329(7), c = 10.2460(13) Å, Z = 4, space group P2₁2₁2₁; those of 11b are monoclinic, a = 11.227(2), b = 9.967(2), c = 17.0537(4) Å, β = 105.4179(5)°, Z = 4, space group P2₁/n; those of 19 are monoclinic, a = 11.1847(15), b = 13.715(3), c = 11.5559(5) Å, β = 104.8730(10)°, Z = 4, space group P2₁/n. The structures were solved by direct methods and refined by full-matrix least-squares procedures to R(F, I [Formula: see text] 3σ(I)) = 0.049, 0.047, 0.042, and 0.047, respectively, for CCD data for 5d, 9a, 11b, and 19. The four molecules contain five-, seven-, six-, and five-membered rings, respectively, with O-B-N groups in the 5d, 11b, and 19, and O-B-O in 9a; the rings exhibit various deviations from planarity, particularly the seven-membered ring.Key words: diarylboron chelates, hydroxyoximes, hydroxynitrones, carboxyoximes, carboxynitrones, organoboron compounds, crystal structure.

  已合成2-和3-羟基亚硝基酮的二芳基硼螯合物，2-和3-羟基肟的二芳基硼螯合物，以及2-羧基亚硝基酮和2-羧基肟。这些结构是通过光谱数据和对5d、9a、11b和19的X射线分析确定的。5d的晶体（在180K）为单斜晶系，a = 10.543(2) Å，b = 19.085(4) Å，c = 10.2667(3) Å，β = 90.4978(7)°，Z = 4，空间群P21/c；9a的晶体为正交晶系，a = 10.9913(5) Å，b = 14.9329(7) Å，c = 10.2460(13) Å，Z = 4，空间群P212121；11b的晶体为单斜晶系，a = 11.227(2) Å，b = 9.967(2) Å，c = 17.0537(4) Å，β = 105.4179(5)°，Z = 4，空间群P21/n；19的晶体为单斜晶系，a = 11.1847(15) Å，b = 13.715(3) Å，c = 11.5559(5) Å，β = 104.8730(10)°，Z = 4，空间群P21/n。这些结构是通过直接方法解决的，并通过全矩阵最小二乘法进行了精细化处理，对于5d、9a、11b和19的CCD数据，分别为R(F, I [Formula: see text] 3σ(I)) = 0.049、0.047、0.042和0.047。这四种分子分别包含五、七、六和五元环，其中5d、11b和19含有O-B-N基团，9a含有O-B-O基团；这些环体现出各种与平面性的偏差，特别是七元环。关键词：二芳基硼螯合物、羟基肟、羟基亚硝基酮、羧基肟、羧基亚硝基酮、有机硼化合物、晶体结构。
• Wessely, Monatshefte fur Chemie, 1900, vol. 21, p. 220
  作者：Wessely

  DOI：——

  日期：——
• Second messenger-dependent protein kinases and protein synthesis regulate endogenous secretin receptor responsiveness
  作者：Roxana S Ghadessy、Eamonn Kelly

  DOI：10.1038/sj.bjp.0704655

  日期：2002.4

  The present study investigated the role of second messenger‐dependent protein kinase A (PKA) and C (PKC) in the regulation of endogenous secretin receptor responsiveness in NG108‐15 mouse neuroblastoma×rat glioma hybrid cells.In whole cell cyclic AMP accumulation studies, activation of PKC either by phorbol 12‐myristate 13‐acetate (PMA) or by purinoceptor stimulation using uridine 5′‐triphosphate (UTP) decreased secretin receptor responsiveness. PKC activation also inhibited forskolin‐stimulated cyclic AMP accumulation but did not affect cyclic AMP responses mediated by the prostanoid‐IP receptor agonist iloprost, or the A2adenosine receptor agonist 5′‐(N‐ethylcarboxamido) adenosine (NECA).In additivity experiments, saturating concentrations of secretin and iloprost were found to be additive in terms of cyclic AMP accumulation, whereas saturating concentrations of NECA and iloprost together were not. This suggests compartmentalization of Gs‐coupling components in NG108‐15 cells and possible heterologous regulation of secretin receptor responsiveness at the level of adenylyl cyclase activation.Cells exposed to the PKA inhibitor H‐89, exhibited a time‐dependent increase in secretin receptor responsiveness compared to control cells. This effect was selective since cyclic AMP responses to forskolin, iloprost and NECA were not affected by H‐89 treatment. Furthermore, treatment with the protein synthesis inhibitor cycloheximide produced a time‐dependent increase in secretin receptor responsiveness.Together these results indicate that endogenous secretin receptor responsiveness is regulated by PKC, PKA and protein neosynthesis in NG108‐15 cells.British Journal of Pharmacology(2002)135, 2020–2028; doi:10.1038/sj.bjp.0704655
• The 2-Cyano-2,2-dimethylethanimine-<i>N</i>-oxymethyl Group for the 2′-Hydroxyl Protection of Ribonucleosides in the Solid-Phase Synthesis of RNA Sequences
  作者：Jacek Cieślak、Cristina Ausín、Andrzej Grajkowski、Serge L. Beaucage

  DOI：10.1002/chem.201204235

  日期：2013.4.2

  reaction of 2‐cyano‐2‐methyl propanal with 2′‐O‐aminooxymethylribonucleosides leads to stable and yet reversible 2′‐O‐(2‐cyano‐2,2‐dimethylethanimine‐N‐oxymethyl)ribonucleosides. Following N‐protection of the nucleobases, 5′‐dimethoxytritylation and 3′‐phosphitylation, the resulting 2′‐protected ribonucleoside phosphoramidite monomers are employed in the solid‐phase synthesis of three chimeric RNA sequences

  2-氰基-2-甲基丙醛与2'- O-氨氧基甲基核糖核苷的反应可产生稳定且可逆的2' - O-（2-氰基-2-2,2-二甲基乙胺-N-氧甲基）核糖核苷。在对核碱基进行N-保护，5'-二甲氧基三苯甲基化和3'-磷酸化之后，得到的2'-保护的核糖核苷亚磷酰胺单体被用于三个嵌合RNA序列的固相合成，每个序列的嘌呤/嘧啶比率不同。在5‐苄硫基‐1 H存在下进行亚磷酰胺单体的活化时-四唑，在180 s内平均获得99％的耦合效率。RNA链装配完成后，在标准碱性条件下进行核苷酸碱基和磷酸盐保护基的去除以及从固相支持物中释放序列，而2' - O-（2-氰基-2，通过用氟化四正丁基铵（0.5  m）处理可实现2-二甲基乙胺基-N-氧甲基）保护基（不释放RNA烷基化副产物）在干燥的DMSO中于55°C下放置24–48 h。通过聚丙烯酰胺凝胶电泳（PAGE），酶水解和基质辅助激光解吸/电离（MALDI）质谱对完全
• Kern,J.M.; Federli,P., Bulletin de la Societe Chimique de France, 1972, p. 4379 - 4383
  作者：Kern,J.M.、Federli,P.

  DOI：——

  日期：——