N-Boc-4-hydroxy-5-methyl-pyrrolidin-2-one | 203929-64-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: N-Boc-4-hydroxy-5-methyl-pyrrolidin-2-one
• 英文别名: (4S,5R)-1-(tert-butyloxycarbonyl)-4-hydroxy-5-methyl-2-pyrrolidinone；tert-butyl (2R,3S)-3-hydroxy-2-methyl-5-oxopyrrolidine-1-carboxylate
• CAS: 203929-64-0
• 化学式: C₁₀H₁₇NO₄
• 分子量: 215.249
• InChiKey: KISRHDLCFAHVPK-RQJHMYQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙醇 、 N-Boc-4-hydroxy-5-methyl-pyrrolidin-2-one 在 potassium cyanide 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到(3S,4R)-4-[(tert-butyloxycarbonyl)amino]-3-hydroxypentanoic acid ethyl ester
  参考文献：
  名称：

  Diastereospecific formal synthesis of (2R,3S)-2-amino-tetradeca-5,7-dien-3-ol isolated from Xestospongia sp.

  摘要：

  Stereospecific synthesis of a common precursor of several acyclic (2R,3S)-2-amino-3-ols from marine origin, especially of (2R,3S)-2-amino-tetradeca-5,7-dien-3-ol isolated from Xestospongia sp., is described starting from the versatile epoxide 10. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01097-8
• 作为产物：
  描述：

  (4S,5R)-4-benzyloxy-1-(4-methoxybenzyl)-5-methyl-2-pyrrolidinone 在 palladium on activated charcoal 4-二甲氨基吡啶 、 ammonium cerium(IV) nitrate 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 水 、 乙腈 为溶剂， 23.0 ℃ 、101.33 kPa 条件下， 反应 182.0h， 生成 N-Boc-4-hydroxy-5-methyl-pyrrolidin-2-one
  参考文献：
  名称：

  A flexible non-amino acid-based formal asymmetric synthesis of naturally occurring (2R,3S)-2-aminotetradeca-5,7-dien-3-ol: observation of a remarkable protecting group effect

  摘要：

  A flexible non-amino acid-based formal asymmetric synthesis of naturally occurring antimicrobial (2R,3S)-2-aminotetradeca-5,7-dien-3-ol is reported. The method features a flexible and highly regioselective Grignard addition to (S)-malimide followed by a trans-diastereoselective reductive deoxygenation. The scope and limitations of the highly regio and diastereoselective reductive alkylation of malimides were defined. A remarkable protecting group effect on the regio and diastereoselective reductive alkylation of malimides was observed. (C) 2003 Published by Elsevier Ltd.

  DOI：

  10.1016/s0957-4166(03)00442-7

文献信息

• Cu‐Catalyzed Asymmetric Kinetic Boron Conjugate Addition of γ‐Substituted α,β‐Unsaturated γ‐Lactams
  作者：Liang Tang、Yicong Luo、Cheng Sheng、Fang Xie、Wanbin Zhang

  DOI：10.1002/anie.202304640

  日期：2023.6.19

  A Cu-catalyzed asymmetric kinetic boron conjugate addition of γ-substituted α,β-unsaturated γ-lactams followed by oxidation is reported with good results. This strategy provides an efficient access to valuable enantioenriched α,β-unsaturated γ-lactams bearing simple γ-alkyl or aryl substituents, which showed inhibitory activities against cisplatin-sensitive ovarian cancer cells A2780. A new Lewis acid

  据报道，Cu 催化的 γ-取代的 α,β-不饱和 γ-内酰胺的不对称动态硼共轭加成反应随后进行氧化，取得了良好的结果。该策略提供了一种有效获得有价值的对映体富集的α,β-不饱和γ-内酰胺的途径，该内酰胺带有简单的γ-烷基或芳基取代基，其对顺铂敏感的卵巢癌细胞A2780表现出抑制活性。提出了一种新的路易斯酸铜催化机理。
• Diastereospecific formal synthesis of (2R,3S)-2-amino-tetradeca-5,7-dien-3-ol isolated from Xestospongia sp.
  作者：Nicole Langlois

  DOI：10.1016/s0040-4039(01)01097-8

  日期：2001.8

  Stereospecific synthesis of a common precursor of several acyclic (2R,3S)-2-amino-3-ols from marine origin, especially of (2R,3S)-2-amino-tetradeca-5,7-dien-3-ol isolated from Xestospongia sp., is described starting from the versatile epoxide 10. (C) 2001 Elsevier Science Ltd. All rights reserved.
• A flexible non-amino acid-based formal asymmetric synthesis of naturally occurring (2R,3S)-2-aminotetradeca-5,7-dien-3-ol: observation of a remarkable protecting group effect
  作者：Bi-Yan He、Tian-Jun Wu、Xian-Yong Yu、Pei-Qiang Huang

  DOI：10.1016/s0957-4166(03)00442-7

  日期：2003.7

  A flexible non-amino acid-based formal asymmetric synthesis of naturally occurring antimicrobial (2R,3S)-2-aminotetradeca-5,7-dien-3-ol is reported. The method features a flexible and highly regioselective Grignard addition to (S)-malimide followed by a trans-diastereoselective reductive deoxygenation. The scope and limitations of the highly regio and diastereoselective reductive alkylation of malimides were defined. A remarkable protecting group effect on the regio and diastereoselective reductive alkylation of malimides was observed. (C) 2003 Published by Elsevier Ltd.