(S)-(-)-Nicotine N-1'-oxide | 51020-67-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (S)-(-)-Nicotine N-1'-oxide
• 英文别名: trans-Nicotine-1'-oxide；3-((2S)-1c-methyl-1t-oxy-pyrrolidin-2r-yl)-pyridine；nicotine (1'R)-1'-oxide；3-((2S)-1c-Methyl-1t-oxy-pyrrolidin-2r-yl)-pyridin；Nicotin-N-oxid；Pyridine, 3-((1R,2S)-1-methyl-1-oxido-2-pyrrolidinyl)-；3-[(1R,2S)-1-methyl-1-oxidopyrrolidin-1-ium-2-yl]pyridine
• CAS: 51020-67-8
• 化学式: C₁₀H₁₄N₂O
• 分子量: 178.234
• InChiKey: RWFBQHICRCUQJJ-CMPLNLGQSA-N

物化性质

• 溶解度：
  可溶于氯仿（少许）、水（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  31
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  烟碱 在 cyclohexanone monooxygenase Α-D-吡喃葡萄糖6-磷酸 、 氧气 、 烟酰胺腺嘌呤双核苷酸磷酸盐 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以32%的产率得到(S)-(-)-Nicotine N-1'-oxide
  参考文献：
  名称：

  First asymmetric oxidation of tertiary amines by cyclohexanone monooxygenase

  摘要：

  Cyclohexanone monooxygenase catalyzes the asymmetric oxidation of some tertiary amines to amine N-oxides. The structure of the amine markedly influences the enantiomeric excess of products. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01780-3

文献信息

• Concentrated Aqueous Peroxodicarbonate: Efficient Electrosyn‐ thesis and Use as Oxidizer in Epoxidations, <i>S</i> ‐, and <i>N</i> ‐Oxidations
  作者：Ann‐Katrin Seitz、Philipp J. Kohlpaintner、Tim van Lingen、Marco Dyga、Fiona Sprang、Michael Zirbes、Siegfried R. Waldvogel、Lukas J. Gooßen

  DOI：10.1002/anie.202117563

  日期：2022.6.20

  electrochemical synthesis of concentrated (≈1.0 m) peroxodicarbonate solutions was achieved by a newly designed electrolysis cell with an elaborate heat-transfer system, a ternary K2CO3/Na2CO3/KHCO3 electrolyte, and the use of high current densities of above 3 A cm−2. Peroxodicarbonate solutions were shown to be powerful and green oxidizers, permitting N- and S-oxidations as well as epoxidations.

  浓缩（≈1.0  m）过氧二碳酸盐溶液的电化学合成是通过一个新设计的电解池实现的，该电解池具有精细的传热系统、三元 K 2 CO 3 /Na 2 CO 3 /KHCO 3电解质，并使用大电流3 A cm -2以上的密度。过氧二碳酸盐溶液被证明是强大的绿色氧化剂，允许N - 和S -氧化以及环氧化。
• Beckett et al., Xenobiotica, 1973, vol. 3, p. 557
  作者：Beckett et al.

  DOI：——

  日期：——
• Gol'dfarb; Sworykina, Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1958, p. 748,754; engl. Ausg. S. 722, 727
  作者：Gol'dfarb、Sworykina

  DOI：——

  日期：——
• Kisaki et al., Journal of the Agricultural Chemical Society of Japan, 1959, vol. 23, p. 454
  作者：Kisaki et al.

  DOI：——

  日期：——
• Diastereospecific kinetics of nicotine<i>N</i>-oxidation in rat liver microsomes
  作者：M. NAKAJIMA、K. IWATA、T. YOSHIDA、T. YAMAMOTO、Y. KUROIWA

  DOI：10.1080/004982598239632

  日期：1998.1

  1. In kinetic studies, both Eadie-Hofstee plots for cis- and trans-nicotine-1'-N-oxide formation from nicotine in rat liver microsomes were linear. For the formation of cis- and trans-nicotine-1'-N-oxide, the apparent K-m were 0.240 +/- 0.069 and 1.524 +/- 0.951 mM respectively. Corresponding V-max were 1.52 +/- 0.48 and 1.19 +/- 0.74 nmol/mg/min respectively.2. The formation of cis-nicotine-1'-N-oxide was greater than the formation of transnicotine-1'-N-oxide in rat liver microsomes and the intrinsic clearance of cis-nicotine-1'-N-oxide formation was 8.1-fold greater than that of trans-nicotine-1'-N-oxide formation.3. The formation of both cis- and trans-nicotine-1'-N-oxide in rat liver microsomes was inhibited by the addition of 1-(1-naphthyl)-2-thiourea or by heat-treatment of microsomes. 2-Diethylaminoethyl-2, 2-diphenylvalerate (SKF525A) and carbon monoxide did not affect these activities even at high concentrations.4. Formations of cis- and trans-nicotine-1'-N-oxide correlated significantly with each other (r = 0.862, p < 0.01). These results suggested that the same flavin-containing monooxygenase (FMO) isoform is responsible for the formation of cis- and trans-nicotine-1'-N-oxide in rat liver.