(Bis-trimethylsilanyl-methyl)-[(E)-3-phenyl-prop-2-en-(E)-ylidene]-amine | 123017-04-9

• 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: (Bis-trimethylsilanyl-methyl)-[(E)-3-phenyl-prop-2-en-(E)-ylidene]-amine
• 英文别名: (E,E)-N-[bis(trimethylsilyl)methyl]-3-phenylprop-2-en-1-imine
• CAS: 123017-04-9
• 化学式: C₁₆H₂₇NSi₂
• 分子量: 289.568
• InChiKey: ZUSBEDSBQQFLFY-OZZAOFPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.89
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  12.36
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (Bis-trimethylsilanyl-methyl)-[(E)-3-phenyl-prop-2-en-(E)-ylidene]-amine 在 二甲基硫 、 臭氧 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 20.17h， 生成
  参考文献：
  名称：

  A Contribution to the Asymmetric Synthesis of 3-Amino β-Lactams: The Diastereoselective [2+2] Cycloaddition Reaction of Chiral Aminoketene Equivalents with Enolizable Aldehyde-Derived Imines

  摘要：

  AbstractN‐[Bis(trimethylsilyl)methyl]imines 9 show unique chemical properties when compared with conventional imines. Their reaction with optically pure aminoketenes derived from dehydrochlorination of 14 and 15 affords the corresponding 3‐amino‐4‐alkyl‐β‐lactams 16 and 17 in good yields and high diastereoselectivities. The mild deprotection of bis(trimethylsilyl)methyl‐ and phenyloxazolidinone moieties with, respectively, cerium(IV) ammonium nitrate and lithium/ammonia or hydrogen/Pd(OH)2 allows the preparation of a variety of β‐lactam antibiotic building blocks.

  DOI：

  10.1002/chem.19970030909
• 作为产物：
  描述：

  二(三甲基硅基)甲胺 、 肉桂醛 在 MS 4A 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以97%的产率得到(Bis-trimethylsilanyl-methyl)-[(E)-3-phenyl-prop-2-en-(E)-ylidene]-amine
  参考文献：
  名称：

  A Contribution to the Asymmetric Synthesis of 3-Amino β-Lactams: The Diastereoselective [2+2] Cycloaddition Reaction of Chiral Aminoketene Equivalents with Enolizable Aldehyde-Derived Imines

  摘要：

  AbstractN‐[Bis(trimethylsilyl)methyl]imines 9 show unique chemical properties when compared with conventional imines. Their reaction with optically pure aminoketenes derived from dehydrochlorination of 14 and 15 affords the corresponding 3‐amino‐4‐alkyl‐β‐lactams 16 and 17 in good yields and high diastereoselectivities. The mild deprotection of bis(trimethylsilyl)methyl‐ and phenyloxazolidinone moieties with, respectively, cerium(IV) ammonium nitrate and lithium/ammonia or hydrogen/Pd(OH)2 allows the preparation of a variety of β‐lactam antibiotic building blocks.

  DOI：

  10.1002/chem.19970030909

文献信息

• Fluoride ion mediated peterson alkenation of bis(trimethylsilyl)methylimines: a novel synthesis of 2-aza-1,3-dienes and N-vinyl-β-lactams
  作者：Juan Lasarte、Claudio Palomo、Jean P. Picard、Jacques Dunogues、Jesús M. Aizpurua

  DOI：10.1039/c39890000072

  日期：——

  The formation of bis(trimethylsily)methylimines and their transformation into aza-1,3-dienes by means of a fluoride-induced catalytic Peterson alkenation is reported; when the procedure was applied to N-[bis(trimethylsilyl)methyl]-azetidin-2-ones, a wide range of N-vinyl derivatives were obtained in high yields.

  据报道，双（三甲基甲硅烷基）甲基亚胺的形成及其通过氟化物催化的彼得森烯化反应转变成氮杂1,3-二烯；当将该方法用于N- [双（三甲基甲硅烷基）甲基]-氮杂环丁烷-2-酮时，可以高收率获得各种N-乙烯基衍生物。
• A novel highly stereoselective synthesis of pyrrolidines and their derivatives through thermal cyclization reaction of N-[bis(trimethylsilyl)methyl]-1-aza-1,3-dienes
  作者：Claudio Palomo、Jesus M. Aizpurua、Jesus M. García、Marta Legido

  DOI：10.1039/c39910000524

  日期：——

  The first example of the thermal intramolecular cyclization of N-[bis(trimethylsilyl)methyl]-1-aza-1,3-dienes to give 5-trimethylsilyl-Δ2-pyrrolines is reported; two straightforward and highly Stereoselective routes to 3,4-disubstituted-5-trimethylsilyl-Δ1pyrrolines and 3,4-disubstituted-2-trimethylsilylpyrrolidines are also described.

  报道了 N-[双(三甲基甲硅烷基)甲基]-1-氮杂-1,3-二烯热分子内环化生成 5-三甲基甲硅烷基-Δ2-吡咯啉的第一个例子；还描述了两种直接且高度立体选择性的3,4-二取代-5-三甲基甲硅烷基-Δ1吡咯啉和3,4-二取代-2-三甲基甲硅烷基吡咯烷路线。
• LASARTE, JUAN;PALOMO, CLAUDIO;PICARD, JEAN P.;DUNOGUES, JACQUES;AIZPURUA,+, J. CHEM. SOC. CHEM. COMMUN.,(1989) N, C. 72-74
  作者：LASARTE, JUAN、PALOMO, CLAUDIO、PICARD, JEAN P.、DUNOGUES, JACQUES、AIZPURUA,+

  DOI：——

  日期：——