1-Morpholino-2-nitropropene | 123168-32-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 1-Morpholino-2-nitropropene
• 英文别名: 4-[(1E)-2-nitro-1-propenyl]morpholine；4-[(E)-2-nitroprop-1-enyl]morpholine
• CAS: 123168-32-1
• 化学式: C₇H₁₂N₂O₃
• 分子量: 172.184
• InChiKey: QDFFEVUNLGYYDG-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  58.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-Morpholino-2-nitropropene 、 L-脯氨醇 以 甲醇 为溶剂， 以97%的产率得到(E)-1-<(S)-2-hydroxymethylpyrrolidin-1-yl>-2-nitropropene
  参考文献：
  名称：

  An improved asymmetric nitroolefination of α-alkyl-γ- and δ-lactones with modified nitroenamines

  摘要：

  New chiral nitroenamines 4a, b were found to be very effective for asymmetric nitroolefination of alpha-alkyl-gamma- and delta-lactones. The enantiomeric excess of the product ran up to 99%. A possible chelation model for the transition state of the asymmetric nitroolefination was discussed.

  DOI：

  10.1016/0040-4039(94)02175-b
• 作为产物：
  描述：

  吗啉 、 硝基乙烷 、 原甲酸三乙酯 在 对甲苯磺酸 作用下， 反应 3.0h， 以71%的产率得到1-Morpholino-2-nitropropene
  参考文献：
  名称：

  Stereoselective Nitroolefination of Active Methine of Various Carbonyl Compounds with β-Nitroenamines

  摘要：

  具有甲亚甲基α碳的羰基化合物的烯醇盐在与β-硝基胺反应时，通过加成消除过程发生2-硝基-1-烯烃化（硝基烯烃化），形成与羰基团相邻的四级碳原子。得到的硝基烯烃的几何构型被证明为E型。

  DOI：

  10.1055/s-1987-28065

文献信息

• An efficient asymmetric synthesis of nitroolefinic lactones with chiral nitroenamines possessing bulky chiral leaving groups
  作者：Xiaowu Yang、Rui Wang

  DOI：10.1016/s0957-4166(97)00452-7

  日期：1997.10

  An efficient asymmetric nitroolefination of enolates 4a-c, 5 afforded multifunctional group nitroolefinic lactones 7a-e and 8a,b containing stereogenic quaternary carbon centers using bulky chiral nitroenamines 1a,b–3a,b as chiral auxiliaries. Studies on the effect of the bulkiness of leaving group showed that bulky nitroenamines 1a,b gave higher ees and yields than those of the less bulky 2a,b–3a

  有效的烯醇盐4a-c，5的不对称硝基烯烃化反应，使用了庞大的手性亚硝胺1a，b-3a，b作为手性助剂，从而得到了多官能团的硝基烯烃内酯7a-e和8a，b，其中含有立体生成的季碳中心。研究的离去基团的体积的效果表明，笨重nitroenamines 1A，B，得到更高EES和产量比那些不太笨重的图2a，2b-3A，3B。提出了一种可能的循环跃迁模型，以阐明S的选择性。
• An Asymmetric Nitroolefination of α-Alkyl-γ-and δ-Lactones with Modified Nitroenamines
  作者：Kiyoharu Nishide、Ryuichi Kurosaki、Kouichi Hosomi、Hitoshi Imazato、Takehisa Inoue、Manabu Node、Toshiumi Ohmori、Kaoru Fuji

  DOI：10.1016/0040-4020(95)00683-y

  日期：1995.10

  New chiral nitroenamines 4a,b having (S)-2-t-butyldimethylsiloxymethylpyrrolidine as an auxiliary were found to be very effective for asymmetric nitroolefination of alpha-alkyl-gamma- and delta-lactones. The enantiomeric excess of the product increased remarkably in the reaction with gamma-lactones compared with previous nitroenamines 1a,b. A possible chelation model for the transition state of the asymmetric nitroolefination is discussed.
• On the reactivity of some 2-methyleneindolines with β-nitroenamines, α-nitroalkenes, and 1,2-diaza-1,3-butadienes
  作者：Orazio A. Attanasi、Gianfranco Favi、Paolino Filippone、Cristina Forzato、Gianluca Giorgi、Stefano Morganti、Patrizia Nitti、Giuliana Pitacco、Egon Rizzato、Domenico Spinelli、Ennio Valentin

  DOI：10.1016/j.tet.2006.04.027

  日期：2006.6

  A study of the behaviour of some electron-rich 2-methyleneindolines (1-3) with different electron-poor reagents (formation of new carbon-carbon and nitrogen-carbon bonds) has furnished interesting results from both synthetic and the mechanistic viewpoints. Enamines 1-3 have been reacted with the beta-nitroenamines 4-7 (reaction CeCl3 center dot 7H(2)O promoted), giving the polymethine dyes 14-23. The same bases 1-3 have been nitroalkylated with the nitroolefins 8-10, furnishing the indolines 24-32, and the diastereoselectivity of the reaction has been thoroughly investigated. The most unexpected results derived from the first example of reaction of Fischer's bases with 1,2-diaza-1,3-butadienes. In fact, with 11-13, the 'unknown' indoline spirodihydropyrroles 33-40 were formed. Their structures were unambiguously assigned, and we determined, as an example, that of 33 by X-ray analysis. (c) 2006 Elsevier Ltd. All rights reserved.
• Direct asymmetric synthesis of quaternary carbon centers by the addition-elimination process: nitroolefination of .alpha.-substituted .delta.-lactones
  作者：Kaoru Fuji、Manabu Node、Hideko Nagasawa、Yoshimitsu Naniwa、Tooru Taga、Katsunosuke Machida、Guenter Snatzke

  DOI：10.1021/ja00202a037

  日期：1989.9
• Asymmetric induction via addition-elimination process: nitroolefination of .alpha.-substituted lactones
  作者：Kaoru. Fuji、Manabu. Node、Hideko. Nagasawa、Yoshimitsu. Naniwa、Shunji. Terada

  DOI：10.1021/ja00273a065

  日期：1986.6