1-veratryl-piperidine | 109247-02-1

• 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-veratryl-piperidine
• 英文别名: 1-Veratryl-piperidin；1-(3,4-Dimethoxybenzyl)piperidine；1-[(3,4-dimethoxyphenyl)methyl]piperidine
• CAS: 109247-02-1
• 化学式: C₁₄H₂₁NO₂
• 分子量: 235.326
• InChiKey: LRGXWZGYKVCSRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3,4-二甲氧基苄醇 在 氯化亚砜 、 苯 作用下， 生成 1-veratryl-piperidine
  参考文献：
  名称：

  Hejno; Arnold, Chemicke Listy, 1953, vol. 47, p. 601,604

  摘要：

  DOI：

文献信息

• Towards the Development of Frustrated Lewis Pair (FLP) Catalyzed Hydrogenations of Tertiary and Secondary Carboxylic Amides
  作者：Jan Paradies、Laura Köring、Nikolai A. Sitte

  DOI：10.1055/a-1681-3972

  日期：2022.3

  The development of the frustrated Lewis pair catalyzed hydrogenation of tertiary and secondary amides is reviewed. Detailed insight into our strategies in order to overcome challenges during the reaction development process is provided. Furthermore, the developed chemistry is extended to the hydrogenation of polyamides and of trifluoroacetamides for the convenient introduction of trifluoroethyl groups into organic molecules.

  标题：摘要 发表了对受挫的Lewis酸碱对催化的三级和二级酰胺氢化的发展进行回顾。提供了我们在克服反应开发过程中的挑战时所采取的策略的详细洞察。此外，开发的化学方法还延伸到聚酰胺和三氟乙酰胺的氢化，以便将三氟乙基基团方便地引入有机分子中。
• Manipulation of substituents at nitrogen in tropanes, homotropanes, and dehydro- derivatives
  作者：Nicola M. Howarth、John R. Malpass、Craig R. Smith

  DOI：10.1016/s0040-4020(98)00643-7

  日期：1998.9

  Trop-6-ene (8-methyl-8-azabicyclo[3.2.1]oct-6-ene) and substituted N-benzylnortrop-6-enes are synthesised. N-Debenzylation of tropanes fails using a wide variety of non-hydrogenolytic conditions despite effective application in model piperidine derivatives; debenzylation of homotropanes is more successful, giving norhomotropane and norhomotrop-7-ene. Bridged N-benzyl compounds react more slowly than N-methyl analogues with chloroformates; the resulting quaternary intermediates are more prone than the N-methyl analogues to suffer competitive reversion to the starting amine, especially in the tropanes, consistent with slower S(N)2 attack at the benzylic carbon during decomposition; the use of an N-p-methoxybenzyl group does allow partial debenzylation to nortrop-6-ene, suggesting greater SNI character in the decomposition step in this case. 'Equatorial' attack is preferred in methylation of N-benzyl-nortrop-6-ene and -homotrop-7-ene with CH3I; subsequent reductive debenzylation of the quaternary salt achieves overall replacement of N-benzyl by N-methyl in both cases. VT NMR studies show the presence of a single 'equatorial' invertomer (Cl syn- to the 2C-bridge) in N-chloro-norhomotropanes and -7-enes and, by analogy, in the N-alkyl compounds. (C) 1998 Elsevier Science Ltd. All rights reserved.