N-(2-propenyl)-2,3-O-isopropylidene-D-glyceraldehyde imine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(2-propenyl)-2,3-O-isopropylidene-D-glyceraldehyde imine
• 英文别名: 1-(2,2-dimethyl-1,3-dioxolan-4-yl)-N-prop-2-enylmethanimine
• 化学式: C₉H₁₅NO₂
• 分子量: 169.224
• InChiKey: ACYUMTRYTINKGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-propenyl)-2,3-O-isopropylidene-D-glyceraldehyde imine 在 草酰氯 、 sodium methylate 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 18.33h， 生成 (-)-(4S)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(2-propenyl)-azetidine-2,3-dione
  参考文献：
  名称：

  Metal-Mediated Carbonyl-1,3-butadien-2-ylation by 1,4-Bis(methanesulfonyl)-2-butyne or 1,4-Dibromo-2-butyne in Aqueous Media:  Asymmetric Synthesis of 3-Substituted 3-Hydroxy-β-lactams

  摘要：

  Metal-mediated 1,3-butadien-2-ylation reactions between 1,4-dibromo-2-butyne or 1,4-bis(methanesulfonyl)-2-butyne and optically pure azetidine-2,3-diones were investigated in aqueous media, offering a convenient asymmetric entry to the potentially bioactive 3-substituted 3-hydroxy-beta-lactam moiety. The diastereoselectivity of the addition reaction was controlled by the bulky chiral auxiliary at C4. However, while the regioselectivity of the process was full, the chemical yield of the addition was a function of the nature of both the metal reagent and the system solvent as well. In addition, 2-azetidinone-tethered 1,3-butadienes can easily be transformed into other functionalities via Diels-Alder reaction.

  DOI：

  10.1021/jo016247b

文献信息

• A Novel Use of Grubbs' Carbene. Application to the Catalytic Deprotection of Tertiary Allylamines
  作者：Benito Alcaide、Pedro Almendros、Jose M. Alonso、Moustafa F. Aly

  DOI：10.1021/ol0167412

  日期：2001.11.1

  [reaction--see text] The first examples accounting for the catalytic deprotection of allylic amines by using reagents different from palladium catalysts have been achieved via Grubbs' carbene-mediated reaction. The current mechanistic hypothesis invokes a nitrogen-assisted ruthenium-catalyzed isomerization, followed by hydrolysis of the enamine intermediate. We believe that an unprecedented mode of ring

  [反应-见正文]通过使用格鲁布斯的卡宾介导的反应已经获得了第一个说明使用不同于钯催化剂的试剂催化烯丙基胺脱保护的例子。当前的机理假设引起了氮辅助的钌催化的异构化反应，随后水解了烯胺中间体。我们认为，涉及到空前的钌烷环丁烷的开环方式。
• Metal-Mediated Carbonyl-1,3-butadien-2-ylation by 1,4-Bis(methanesulfonyl)-2-butyne or 1,4-Dibromo-2-butyne in Aqueous Media:  Asymmetric Synthesis of 3-Substituted 3-Hydroxy-β-lactams
  作者：Benito Alcaide、Pedro Almendros、Raquel Rodríguez-Acebes

  DOI：10.1021/jo016247b

  日期：2002.3.1

  Metal-mediated 1,3-butadien-2-ylation reactions between 1,4-dibromo-2-butyne or 1,4-bis(methanesulfonyl)-2-butyne and optically pure azetidine-2,3-diones were investigated in aqueous media, offering a convenient asymmetric entry to the potentially bioactive 3-substituted 3-hydroxy-beta-lactam moiety. The diastereoselectivity of the addition reaction was controlled by the bulky chiral auxiliary at C4. However, while the regioselectivity of the process was full, the chemical yield of the addition was a function of the nature of both the metal reagent and the system solvent as well. In addition, 2-azetidinone-tethered 1,3-butadienes can easily be transformed into other functionalities via Diels-Alder reaction.