(R)-1-(2,2-dimethyl-1,3-dioxolan-4-yl)-N-(4-methoxybenzyl)methanimine | 124455-21-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R)-1-(2,2-dimethyl-1,3-dioxolan-4-yl)-N-(4-methoxybenzyl)methanimine
• CAS: 124455-21-6；124455-24-9
• 化学式: C₁₄H₁₉NO₃
• 分子量: 249.31
• InChiKey: VRFXQLNOEULQRZ-NCPSJORJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  40.05
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (R)-1-(2,2-dimethyl-1,3-dioxolan-4-yl)-N-(4-methoxybenzyl)methanimine 在 sodium periodate 、 三甲基氯硅烷 、 三氟乙酸 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 6.0h， 生成 (R)-3,3-Difluoro-1-(4-methoxy-benzyl)-4-oxo-azetidine-2-carboxylic acid
  参考文献：
  名称：

  Reactivity Enhancement for Chiral Dirhodium(II) Tetrakis(Carboxamidates)

  摘要：

  Difluorinated Ligands from azetidinone-4-carboxylates and pyrrolidinone-5-carboxylate have been prepared, substituted onto dirhodium(II), and the reactivities and selectivities of the resulting catalysts have been examined. The fluorinated catalysts exhibit enhanced reactivity towards diazo decomposition but diminished enantioselectivities for cyclopropanation. Selectivity for ylide formation and rearrangement or Si-H insertion is enhanced or similar to that with unfluorinated analogues.

  DOI：

  10.1002/1615-4169(20010129)343:1<112::aid-adsc112>3.0.co;2-m
• 作为产物：
  描述：

  双丙酮-D-甘露糖醇 在 sodium periodate 、 碳酸氢钠 、 magnesium sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 (R)-1-(2,2-dimethyl-1,3-dioxolan-4-yl)-N-(4-methoxybenzyl)methanimine
  参考文献：
  名称：

  Reactivity Enhancement for Chiral Dirhodium(II) Tetrakis(Carboxamidates)

  摘要：

  Difluorinated Ligands from azetidinone-4-carboxylates and pyrrolidinone-5-carboxylate have been prepared, substituted onto dirhodium(II), and the reactivities and selectivities of the resulting catalysts have been examined. The fluorinated catalysts exhibit enhanced reactivity towards diazo decomposition but diminished enantioselectivities for cyclopropanation. Selectivity for ylide formation and rearrangement or Si-H insertion is enhanced or similar to that with unfluorinated analogues.

  DOI：

  10.1002/1615-4169(20010129)343:1<112::aid-adsc112>3.0.co;2-m

文献信息

• Total Synthesis of (−)-4a,5-Dihydrostreptazolin
  作者：Janine Cossy、Isabelle Pévet、Christophe Meyer

  DOI：10.1002/1099-0690(200108)2001:15<2841::aid-ejoc2841>3.0.co;2-w

  日期：2001.8

  (-)-4a,5-Dihydrostreptazolin has been synthesized in nine steps from D-glyceraldehyde acetonide. Key steps include a diastereoselective addition of a vinylic Grignard reagent to an imine derived from D-glyceraldehyde acetonide, a ring-closing metathesis, and a stereoselective radical-mediated enyne cyclization.

  (-)-4a,5-二氢链霉菌素是以D-甘油醛乙酸酐为起始材料，在九步反应中成功合成的。关键步骤包括： 1. 将由D-甘油醛乙酸酐衍生而来的亚胺与烯丙基格氏试剂进行非对映选择性加成； 2. 进行了环闭合反应； 3. 完成了一种立体选择性自由基介导的烯炔环化反应。
• Diastereoselective addition of lithiated N,N-diethyl-o-toluamide to chiral isopropylidine glyceraldehyde lmines. Asymmetric synthesis of 3-substituted 3,4-dihydro-1(2H)-isoquinolones
  作者：Robin D. Clark、Jahangir、Michel Souchet、John R. Kern

  DOI：10.1039/c39890000930

  日期：——

  The lithio derivative of N,N-diethyl-o-toluamide adds regiospecifically to (R)-and (S)-glyceraldehyde acetonide p-methoxybenzyl imines to afford the Cram-chelation controlled products (3S,1′R)-(3) and (3R,1′S)-(3),respectively.

  的锂衍生物Ñ，Ñ二乙基ö -toluAMide区域专一性增加（[R ）-和（小号）甘油醛丙酮化合物p甲氧基苄基亚胺，得到CRAM-螯合控制产品（3小号，1' - [R ）- （3）和（3 R，1 'S）-（3）。
• Chelation control in the addition of homophthalic anhydride to α-alkoxy imines. Pancratistatin model studies.
  作者：Robin D Clark、Michel Souchet

  DOI：10.1016/s0040-4039(00)94368-5

  日期：1990.1

  Diastereoselectivity in the addition of homophthalic anhydride to the α-alkoxy imine ()-5 can be increased dramatically (to > 90%) with addition of Lewis acids. This methodology has been applied to the synthesis of a model compound (12) which contains four asymmetric centers with the same relative stereochemistry as pancratistatin (1).

  通过添加路易斯酸，将高邻苯二甲酸酐添加到α-烷氧基亚胺（）-5中的非对映选择性可以显着提高（> 90％）。该方法已应用于模型化合物（12）的合成，该模型化合物包含四个不对称中心，其相对立体化学与潘克拉斯汀（1）具有相同的相对立体化学。
• Cossy, Janine; Pévet, Isabelle; Meyer, Christophe, Synlett, 2000, # 1, p. 122 - 124
  作者：Cossy, Janine、Pévet, Isabelle、Meyer, Christophe

  DOI：——

  日期：——
• CLARK, ROBIN D.;SOUCHET, MICHEL, TETRAHEDRON LETT., 31,(1990) N, C. 193-196
  作者：CLARK, ROBIN D.、SOUCHET, MICHEL

  DOI：——

  日期：——