rac-1-benzoyl-2-(tert-butyl)tetrahydro-3-methylpyrimidin-4(1H)-one | 131932-56-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: rac-1-benzoyl-2-(tert-butyl)tetrahydro-3-methylpyrimidin-4(1H)-one
• 英文别名: 1-benzoyl-2-tert-butyl-3-methylperhydropyrimidin-4-one；1-benzoyl-tert-butyl-3-methylperhydropyrimidin-4-one；1-Benzoyl-2-tert-butyl-3-methyl-1,3-diazinan-4-one
• CAS: 131932-56-4
• 化学式: C₁₆H₂₂N₂O₂
• 分子量: 274.363
• InChiKey: XEOBSMIUNSHXJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-碘丁烷 、 rac-1-benzoyl-2-(tert-butyl)tetrahydro-3-methylpyrimidin-4(1H)-one 在 lithium diisopropyl amide 作用下， 生成 trans-1-benzoyl-5-n-butyl-2-tert-butyl-3-methylperhydropyrimidin-4-one
  参考文献：
  名称：

  Asymmetric synthesis of .beta.-amino acids. 1. Highly diastereoselective addition of a racemic .beta.-alanine enolate derivative to electrophiles

  摘要：

  beta-Alanine, an inexpensive alpha-amino acid, was converted into the 2-tert-butylperhydropyrimidin-4-one derivative 2, which can be alkylated with high diastereoselectivity via the corresponding enolate. The high stereoselectivity observed for the reaction of 2-Li with electrophiles seems to be due to steric hindrance generated by an axial disposition of the tert-butyl group at C(2), which directs addition from the enolate face opposite to this group. The hydrolysis of the resulting adducts proceeds with 6 N hydrochloric acid to afford alpha-substituted beta-amino acids in good yields. These results pave the road to the development of a new asymmetric synthesis of enantiomerically pure alpha-substituted beta-amino acids.

  DOI：

  10.1021/jo00007a053
• 作为产物：
  描述：

  2-溴苯甲酸酐 在 偶氮二异丁腈 、 苯基乙烯基砜 、 三丁基氯化锡 、 sodium cyanoborohydride 作用下， 以 甲苯 为溶剂， 生成 rac-1-benzoyl-2-(tert-butyl)tetrahydro-3-methylpyrimidin-4(1H)-one
  参考文献：
  名称：

  1,3-Asymmetric Induction via 1,5-Hydrogen Atom Translocation Reactions. Highly Enantioselective Synthesis of β-Substituted β-Amino Acids

  摘要：

  DOI：

  10.1021/ja961484v

文献信息

• CONCISE BETA2-AMINO ACID SYNTHESIS VIA ORGANOCATALYTIC AMINOMETHYLATION
  申请人：CHI Yonggui

  公开号：US20080058548A1

  公开（公告）日：2008-03-06

  The present invention provides a method for the synthesis of β 2 -amino acids. The method also provides methods yielding α-substituted β-amino aldehydes and β-substituted γ-amino alcohols. The present method according to this invention allows for increased yield and easier purification using minimal chromatography or crystallization. The methods described herein are based on an aldehyde aminomethylation which involves a Mannich reaction between an aldehyde and a formaldehyde-derived N,O-acetal (iminium precursor) and a catalyst, such as, for example, L-proline or a pyrrolidine. The invention allows for large scale, commercial preparation of β 2 -amino acids.

  本发明提供了一种合成β2-氨基酸的方法。该方法还提供了产生α-取代β-氨基醛和β-取代γ-氨基醇的方法。根据本发明的现有方法，可以使用最小的色谱或结晶实现增加产量和更容易的纯化。所述方法基于醛氨甲基化反应，包括醛和甲醛衍生的N，O-缩醛（亚胺前体）和催化剂之间的Mannich反应，例如L-脯氨酸或吡咯烷。本发明允许大规模、商业化制备β2-氨基酸。
• Optical resolution of aminoisobutyric acid
  申请人：ELI LILLY AND COMPANY

  公开号：EP1059286A1

  公开（公告）日：2000-12-13

  A process for resolving amino protected racemic 3-amino-2-methylpropionic acid which comprises the steps of: (1) reacting said amino protected acid with a protected amino group with an enantiomer of a chiral amine to form diastereomeric salts; (2) recrystallizing the diastereomeric salts from ethyl acetate to separate the diastereomeric salts into crystal fractions; and (3) releasing the resolved acid from the diastereomeric salt by treating the diastereomeric salt with a basic solution is disclosed. A process for the preparation of the cryptophycin molecules is also disclosed.

  一种用于解析受氨基保护的外消旋 3-氨基-2-甲基丙酸的工艺，包括以下步骤(1) 将所述受氨基保护的酸的受保护氨基与手性胺的对映体反应，形成非对映异构盐；(2) 从乙酸乙酯中重结晶非对映异构盐，将非对映异构盐分离成晶体馏分；(3) 用碱性溶液处理非对映异构盐，从非对映异构盐中释放出已解析的酸。还公开了一种隐翅虫霉素分子的制备工艺。
• X-ray Crystallographic Study of Substituted Perhydropyrimidinones. Extreme Changes in Ring Conformation
  作者：Yara Ramírez-Quirós、Margarita Balderas、Jaime Escalante、Delia Quintana、Itzell Gallardo、Domingo Madrigal、Elies Molins、Eusebio Juaristi

  DOI：10.1021/jo991297q

  日期：1999.11.1

  X-ray crystal structures of 20 differently substituted perhydropyrimidin-4-ones are presented. Analysis of these data reveal a remarkable conformational sensitivity of a six-membered ring to substitution. Thus half-chair; envelope, boat, twist-boat, and intermediate conformations are found for the six-membered heterocycle, providing evidence for a relatively flat conformational energy surface in this ring, interpretation of the preferred conformations is advanced in terms of steric interactions among substituents and, in some cases, as the result of particular conformational (A(1,3) strain, anomeric) effects.
• JUARISTI, EUSEBIO;QUINTANA, DELIA;LAMATSCH, BERND;SEEBACH, DIETER, J. ORG. CHEM., 56,(1991) N, C. 2553-2557
  作者：JUARISTI, EUSEBIO、QUINTANA, DELIA、LAMATSCH, BERND、SEEBACH, DIETER

  DOI：——

  日期：——
• US6372936B1
  申请人：——

  公开号：US6372936B1

  公开（公告）日：2002-04-16