(Z)-3-苯基-1-丙烯基N,n-二异丙基氨基甲酸酯 | 678150-52-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (Z)-3-苯基-1-丙烯基N,n-二异丙基氨基甲酸酯
• 英文名称: (Z)-3-phenyl-1-propenyl N,n-diisopropylcarbamate
• 英文别名: Ofqjqaculfqngm-wqlsenkssa-；[(Z)-3-phenylprop-1-enyl] N,N-di(propan-2-yl)carbamate
• CAS: 678150-52-2
• 化学式: C₁₆H₂₃NO₂
• 分子量: 261.364
• InChiKey: OFQJQACULFQNGM-WQLSENKSSA-N

物化性质

• 沸点：
  367.5±35.0 °C(Predicted)
• 密度：
  1.007±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-3-苯基-1-丙烯基N,n-二异丙基氨基甲酸酯 在 正丁基锂 、 四甲基乙二胺 、 鹰爪豆碱 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 17.92h， 生成 (6R,7S,4Z)-7-(4-bromophenyl)-7-hydroxy-2-methyl-6-phenylhepta-2,4-dien-4-yl N,N-diisopropylcarbamate
  参考文献：
  名称：

  Asymmetric γ-Deprotonation and Homoaldol Reaction of 1,3-Dien-2-yl Carbamates:  Stereo- and Regiochemistry

  摘要：

  [GRAPHICS]Lithium compounds 7 are configurationally stable intermediates obtained by deprotonation of 1,3-dien-2-yl carbamates 6 with n-butyllithium/(-)-sparteine with a high degree of enantiotopic differentiation at the gamma-position. They react with electrophiles regioselectively giving highly enantioenriched products. Starting with different isomers or changing the double-bond geometries in 6 leads to either of the enantiomers.

  DOI：

  10.1021/ol061005p
• 作为产物：
  描述：

  (E)-3-phenyl-2-propenyl N,n-diisopropylcarbamate 在 正丁基锂 、 四甲基乙二胺 、 titanium(IV) isopropylate 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 1.0h， 以80%的产率得到(Z)-3-苯基-1-丙烯基N,n-二异丙基氨基甲酸酯
  参考文献：
  名称：

  Highly Enantioenriched Homoenolate Reagents by Asymmetric γ-Deprotonation of Achiral 1-Silyl-Substituted 1-Alkenyl Carbamates

  摘要：

  1-Trimethylsilyl-1-alkenyl carbamates 1 are deprotonated by n-butyllithium/(-)-sparteine (2) with a high degree of enantiotopic differentiation in the gamma-position to form the enantiomerically enriched allyllithium derivatives 3. Trapping these with several electrophiles proceeds stereospecifically in an anti-S-E' or syn-S-E' substitution to form products 4 or ent-4, respectively. Compounds 3a (R = Me) and 3b (R = Ph) exhibit toward carbonyl electrophiles opposite senses of almost complete stereospecificity, thus for 3b(.)2 the involvement of a eta(3)-complex is suggested.

  DOI：

  10.1021/ol0364677

文献信息

• Asymmetric Synthesis of 3,4-Annulated Cyclopentenones from Cycloalkenyl Ketones and Vinyl Carbamates by Diastereoselective Carbonyl Addition/Conrotatory 4π Ring Closure
  作者：Dieter Hoppe、Michael Siemer、Roland Fröhlich

  DOI：10.1055/s-2008-1067150

  日期：2008.7

  1-Lithiated O-vinyl carbamates add with high induced diastereoselectivity onto enantiomerically pure cycloalk-1-enyl (1-dibenzylamino)alkyl ketones. Subsequent O-carbamoyl migration, followed by a torquoselective, antarafacial 4π ring closure, leads to homochiral 2-substituted bicyclo[n.3.0]alk-1-ene-2-ones.

  1-锂化O-乙烯基氨基甲酸酯以高诱导的非对映选择性与对映体纯的环烯烃(1-二苯基氨基)烷基酮发生反应。随后，O-氨基甲酰迁移，再经过扭转选择性的反面4π环闭合，生成同手性的2-取代双环[n.3.0]烷-1-烯-2-酮。
• Stereoselective Synthesis of Metalated Cyclobutyl Derivatives
  作者：Einav Tsoglin、Helena Chechik、Guy Karseboom、Nicka Chinkov、Amnon Stanger、Ilan Marek

  DOI：10.1002/adsc.200800719

  日期：2009.5

  Abstractmagnified imageTreatment of Z‐vinyl carbamates with dicyclopentadienyl(diethyl)zirconium [Et2ZrCp2] leads to cyclobutyl‐zirconocene derivatives in good yields and as a unique diastereoisomer. The reaction proceeds through a carbometalative ring‐expansion followed by an intramolecular migratory insertion.
• Highly Enantioenriched Homoenolate Reagents by Asymmetric γ-Deprotonation of Achiral 1-Silyl-Substituted 1-Alkenyl Carbamates
  作者：Jenny Reuber、Roland Fröhlich、Dieter Hoppe

  DOI：10.1021/ol0364677

  日期：2004.3.1

  1-Trimethylsilyl-1-alkenyl carbamates 1 are deprotonated by n-butyllithium/(-)-sparteine (2) with a high degree of enantiotopic differentiation in the gamma-position to form the enantiomerically enriched allyllithium derivatives 3. Trapping these with several electrophiles proceeds stereospecifically in an anti-S-E' or syn-S-E' substitution to form products 4 or ent-4, respectively. Compounds 3a (R = Me) and 3b (R = Ph) exhibit toward carbonyl electrophiles opposite senses of almost complete stereospecificity, thus for 3b(.)2 the involvement of a eta(3)-complex is suggested.
• Asymmetric γ-Deprotonation and Homoaldol Reaction of 1,3-Dien-2-yl Carbamates:  Stereo- and Regiochemistry
  作者：Roland Bou Chedid、Roland Fröhlich、Dieter Hoppe

  DOI：10.1021/ol061005p

  日期：2006.7.1

  [GRAPHICS]Lithium compounds 7 are configurationally stable intermediates obtained by deprotonation of 1,3-dien-2-yl carbamates 6 with n-butyllithium/(-)-sparteine with a high degree of enantiotopic differentiation at the gamma-position. They react with electrophiles regioselectively giving highly enantioenriched products. Starting with different isomers or changing the double-bond geometries in 6 leads to either of the enantiomers.

表征谱图