1-methylene-piperidinium | 45457-73-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-methylene-piperidinium
• 英文别名: 1-Methylidenepiperidin-1-ium
• CAS: 45457-73-6
• 化学式: C₆H₁₂N
• 分子量: 98.168
• InChiKey: LCCCAFOMMQBWHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  3
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-methylene-piperidinium 、 5-(7-Hydroxy-2-oxochromen-4-yl)pentanoic acid 以 乙醇 为溶剂， 反应 3.0h， 以45%的产率得到5-[7-Hydroxy-2-oxo-8-(piperidin-1-ylmethyl)chromen-4-yl]pentanoic acid
  参考文献：
  名称：

  Novel 7-hydroxycoumarin based fluorescent labels

  摘要：

  Five new 7-hydroxy-8-(N-alkylaminomethyl)coumarin labels (6a-e) were prepared from 4-(4-carboxybutyl)-7-hydroxycoumarin (4) in 28-48% yield. Compared to 4-methylumbelliferone (4-MU, 1), the new fluorescent labels exhibited higher emission intensity over a broader pH range. Extinction coefficients, quantum yields and pKa values are also reported for these labels. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00345-4
• 作为产物：
  描述：

  哌啶 、 聚合甲醛 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 生成 1-methylene-piperidinium
  参考文献：
  名称：

  Novel 7-hydroxycoumarin based fluorescent labels

  摘要：

  Five new 7-hydroxy-8-(N-alkylaminomethyl)coumarin labels (6a-e) were prepared from 4-(4-carboxybutyl)-7-hydroxycoumarin (4) in 28-48% yield. Compared to 4-methylumbelliferone (4-MU, 1), the new fluorescent labels exhibited higher emission intensity over a broader pH range. Extinction coefficients, quantum yields and pKa values are also reported for these labels. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00345-4

文献信息

• Ring-Expansion Induced 1,2-Metalate Rearrangements: Highly Diastereoselective Synthesis of Cyclobutyl Boronic Esters
  作者：Durga Prasad Hari、Joseph C. Abell、Valerio Fasano、Varinder K. Aggarwal

  DOI：10.1021/jacs.0c00813

  日期：2020.3.25

  2-migrations. Normally, such shifts are induced by α-leaving groups or by reactions of alkenyl boro-nates with electrophiles. Herein, we present a new strategy to in-duce 1,2-metallate rearrangement, via ring expansion of vinylcyclo-propyl boronate complexes activated by electrophiles. This leads to a cyclopropane-stabilized carbocation which triggers ring expansion and concomitant 1,2-metallate rearrangement

  有机硼化合物的广泛合成用途源于它们易于进行 1,2-迁移的能力。通常，这种转变是由α-离去基团或由烯基硼酸酯与亲电子试剂的反应引起的。在此，我们提出了一种新策略，通过亲电子试剂激活的乙烯基环丙基硼酸酯络合物的环扩张来诱导 1,2-金属化物重排。这导致环丙烷稳定的碳正离子引发环膨胀和伴随的 1,2-金属盐重排。这种新工艺提供了具有高水平非对映选择性的药用相关 1,2-取代环丁基硼酸酯。可以使用范围广泛的有机锂和格氏试剂、亲电子试剂和乙烯基环丙基硼酸酯。该方法被应用于 (±)-格兰地醇的短期立体选择性合成。
• Tidwell, Jeffrey H.; Senn, Dwayne R.; Buchwald, Stephen L., Journal of the American Chemical Society, 1991, vol. 113, # 12, p. 4685 - 4686
  作者：Tidwell, Jeffrey H.、Senn, Dwayne R.、Buchwald, Stephen L.

  DOI：——

  日期：——
• Jortay, C.; Flammang, R.; Maquestiau, A., Bulletin des Societes Chimiques Belges, 1985, vol. 94, # 10, p. 727 - 734
  作者：Jortay, C.、Flammang, R.、Maquestiau, A.

  DOI：——

  日期：——
• Réactivité du 3,3-bis(triméthylsilyl)propène vis-à-vis des ions iminium issus d'amines secondaires. Accès stéréosélectif à des (E)-β-aminovinylsilanes
  作者：Bruno Princet、Hélène Gardès-Gariglio、Jacques Pornet

  DOI：10.1016/s0022-328x(00)00232-1

  日期：2000.6

  The 3,3-bis(trimethylsilyl)propene reacts with iminium ions generated in situ from secondary amines by an aminomethylation-desilylation process, leading to (E)-beta-aminovinylsilanes. When a secondary amine with two secondary groups is used, the reaction fails, the steric hindrance probably inhibiting the reaction.
• Novel 7-hydroxycoumarin based fluorescent labels
  作者：Maciej Adamczyk、Michael Cornwell、Jeff Huff、Sushil Rege、Tata Venkata S. Rao

  DOI：10.1016/s0960-894x(97)00345-4

  日期：1997.8

  Five new 7-hydroxy-8-(N-alkylaminomethyl)coumarin labels (6a-e) were prepared from 4-(4-carboxybutyl)-7-hydroxycoumarin (4) in 28-48% yield. Compared to 4-methylumbelliferone (4-MU, 1), the new fluorescent labels exhibited higher emission intensity over a broader pH range. Extinction coefficients, quantum yields and pKa values are also reported for these labels. (C) 1997 Elsevier Science Ltd.