Allyl-[1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-meth-(E)-ylidene]-amine | 358973-81-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Allyl-[1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-meth-(E)-ylidene]-amine
• CAS: 358973-81-6
• 化学式: C₉H₁₅NO₂
• 分子量: 169.224
• InChiKey: ACYUMTRYTINKGP-QMEHYBMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.39
• 重原子数：
  12.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  30.82
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  Allyl-[1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-meth-(E)-ylidene]-amine 在 正丁基锂 、 硫代水杨酸 、 1,4-双(二苯基膦)丁烷 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 14.17h， 生成
  参考文献：
  名称：

  通过钯催化的还原二炔环化立体控制（+）-链霉唑啉的全合成。

  摘要：

  DOI：

  10.1002/anie.200460058
• 作为产物：
  描述：

  丙烯胺 、 双丙酮-D-甘露糖醇 在 sodium periodate 作用下， 以 水 、 1,2-二氯乙烷 为溶剂， 以95%的产率得到Allyl-[1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-meth-(E)-ylidene]-amine
  参考文献：
  名称：

  通过钯催化的还原二炔环化立体控制（+）-链霉唑啉的全合成。

  摘要：

  DOI：

  10.1002/anie.200460058

文献信息

• Straightforward Asymmetric Entry to Highly Functionalized 3-Substituted 3-Hydroxy-β-lactams via Baylis−Hillman or Bromoallylation Reactions
  作者：Benito Alcaide、Pedro Almendros、Cristina Aragoncillo、Raquel Rodríguez-Acebes

  DOI：10.1021/jo035472l

  日期：2004.2.1

  The reaction of various activated vinyl systems, including 2-cyclopenten-1-one, with enantiopure azetidine-2,3-diones 1 was promoted by DABCO to afford the corresponding optically pure Baylis−Hillman adducts 2 without detectable epimerization. However, the reaction of α-keto lactams 1 with but-3-yn-2-one was not as successful, giving the corresponding β-halo Baylis−Hillman adduct in low yield. Metal-mediated

  DABCO促进了各种活化的乙烯基系统（包括2-环戊烯-1-酮）与对映体纯的氮杂环丁烷2,3-二酮1的反应，得到了相应的光学纯的Baylis-Hillman加合物2，而没有可检测的差向异构化。然而，α-酮内酰胺1与but-3-yn-2-one的反应不那么成功，从而以低收率得到了相应的β-卤代Baylis-Hillman加合物。在水介质中研究了金属介导的2，3-二溴丙烯与氮杂环丁烷-2，3-二酮1之间的溴代烯丙基化反应。令人惊讶地，铟不能促进α-酮内酰胺1的溴代烯丙基化反应，但是Sn-Hf 4 Cl促进了酮1的溴代烯丙基化。高效地进行了操作，以得到作为单一非对映异构体的溴高烯丙基醇5。在此基础上，开发了用于潜在生物活性的3个取代的3-羟基-β-内酰胺部分的不对称合成的简单快速的方法。
• Alkyne−Co₂(CO)₆ Complexes in the Synthesis of Fused Tricyclic β-Lactam and Azetidine Systems^,¹
  作者：Benito Alcaide、Concepción Polanco、Miguel A. Sierra

  DOI：10.1021/jo980114h

  日期：1998.10.1

  3a to form tricyclic systems. In fact, the analogous enyne-azetidines 20a,b smoothly cyclized to form the corresponding tricyclic systems. This approach to tricyclic azetidines was extended to prepare different products. A new, unprecedented, N1-C2 bond breakage was also observed in the azetidine ring. The results described show that the P-K reaction is a suitable approach to tricyclic 2-azetidinones

  外消旋和对映体纯，稠合的三环2-氮杂环丁酮和氮杂环丁烷的合成方法已经开发出来，方法是在单环烯炔-β-内酰胺上使用Pauson-Khand（PK）反应作为关键的合成步骤。通过烯炔亚胺8和9与D-甘油醛亚胺10和（苄氧基）-或苯氧基乙酰氯的Staüdinger反应，可获得环化前体单环β-内酰胺1-7。烯炔亚胺8和9形成具有所需烯炔部分的顺式-2-氮杂环丁酮1和2。获得顺式-2-氮杂环丁酮11为单一非对映异构体，并通过标准方法将其转化为烯炔-2-氮杂环丁酮3和5。或者，通过对茴香基乙二醛二亚胺和（苄氧基）乙酰氯的环化反应制备4-甲酰基-2-氮杂环丁烷酮14，并通过标准反应将其转化为外消旋烯炔-β-内酰胺4和6。Enyne-2-azetidinones 1-7与Co（2）（CO）（8）反应以定量产生相应的炔烃-Co（2）（CO）（6）复合物。这种配合物与不同的促进剂，特别是热和TMANO的反应，形
• Metal-Promoted Allylation, Propargylation, or Allenylation of Azetidine-2,3-diones in Aqueous and Anhydrous Media. Application to the Asymmetric Synthesis of Densely Functionalized 3-Substituted 3-Hydroxy-β-lactams
  作者：Benito Alcaide、Pedro Almendros、Cristina Aragoncillo、Raquel Rodríguez-Acebes

  DOI：10.1021/jo015704l

  日期：2001.7.1

  Metal-mediated carbonyl allylation, allenylation, and propargylation of optically pure azetidine-2,3-diones were investigated in both anhydrous and aqueous environments. Different metals promoters showed varied regioselectivities on product formation during allenylation/propargylation reactions of the keto-beta -lactams. The stereochemistry of the new C3-substituted C3-hydroxy quaternary center was controlled by placing a chiral auxiliary at C4. In this way, the coupling of azetidine-2,3-diones with a variety of propenyl-, propynyl-, and allenylmetal reagents offers a convenient asymmetric entry to potentially bioactive 3-substituted 3-hydroxy-beta -lactams.
• A Novel One-Step Approach for the Preparation of α-Amino Acids, α-Amino Amides, and Dipeptides from Azetidine-2,3-diones
  作者：Benito Alcaide、Pedro Almendros、Cristina Aragoncillo

  DOI：10.1002/1521-3765(20020816)8:16<3646::aid-chem3646>3.0.co;2-m

  日期：2002.8.16

  A remarkable reaction of azetidine-2,3-diones with primary as well as secondary amines, and water is presented. Simply by varying the nucleophile, an unprecedented one-step synthesis of alpha-amino acids, alpha-amino amides, and dipeptides, was developed in both the racemic and optically pure forms. The current mechanistic hypothesis invokes a concerted process involving CO extrusion. However, a stepwise pathway can also account for these novel transformations.
• Synthesis of novel 4-(5'-pyrrolidinyl)-β-lactams
  作者：Ronald Grigg、Mark Thornton-Pett、Juan Xu、Long-He Xu

  DOI：10.1016/s0040-4020(99)00867-4

  日期：1999.11

  The synthesis of novel 4-(5'-pynolidinyl)-beta-lactams from imines derived from 4-formyl-beta-lactams and alpha-amino esters via cascade imine-->azomethine ylide-->1,3-dipolar cycloaddition reactions is described. These cascades are endo-specific, exhibit facial stereoselectivity and occur in good to excellent yields. (C) 1999 Elsevier Science Ltd. Ail rights reserved.