1-(3-(tert-butyldimethylsilyloxy)propyl)-2-phenyl-2,3-dihydropyridin-4(1H)-one | 1335247-90-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-(3-(tert-butyldimethylsilyloxy)propyl)-2-phenyl-2,3-dihydropyridin-4(1H)-one
• 英文别名: 1-[3-[Tert-butyl(dimethyl)silyl]oxypropyl]-2-phenyl-2,3-dihydropyridin-4-one
• CAS: 1335247-90-9
• 化学式: C₂₀H₃₁NO₂Si
• 分子量: 345.557
• InChiKey: MDDRMZNNVLUBNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.93
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3-(tert-butyldimethylsilyloxy)propyl)-2-phenyl-2,3-dihydropyridin-4(1H)-one 、 苯基三乙氧基硅烷 在 palladium diacetate 、 copper (II)-fluoride 作用下， 以 溶剂黄146 、 叔丁醇 为溶剂， 反应 3.75h， 以75%的产率得到N-(3'-((tert-butyldimethylsilyl)oxy)propyl)-2,5-diphenyl-2,3-dihydropyridin-4(1H)-one
  参考文献：
  名称：

  Direct Hiyama Cross-Coupling of Enaminones With Triethoxy(aryl)silanes and Dimethylphenylsilanol

  摘要：

  2,3-Dihydropyridin-4(1H)-ones undergo direct C-H functionalization at C5 In the palladium(II)-catalyzed Hiyama reaction, using triethoxy(aryl)silanes and dimethylphenylsilanol. The reagent CuF2 has a dual role In the reactions with triethoxy(aryl)silanes. It Is a source of fluoride to activate the sllane in the Hiyama reaction and also serves as the reoxidant to convert Pd(0) to Pd(II) In the catalytic cycle.

  DOI：

  10.1021/ol202202a
• 作为产物：
  描述：

  (3-溴丙氧基)叔丁基二甲基硅烷 、 4(1H)-吡啶酮,2,3-二氢-2-苯基- 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 24.0h， 以32%的产率得到1-(3-(tert-butyldimethylsilyloxy)propyl)-2-phenyl-2,3-dihydropyridin-4(1H)-one
  参考文献：
  名称：

  Direct Hiyama Cross-Coupling of Enaminones With Triethoxy(aryl)silanes and Dimethylphenylsilanol

  摘要：

  2,3-Dihydropyridin-4(1H)-ones undergo direct C-H functionalization at C5 In the palladium(II)-catalyzed Hiyama reaction, using triethoxy(aryl)silanes and dimethylphenylsilanol. The reagent CuF2 has a dual role In the reactions with triethoxy(aryl)silanes. It Is a source of fluoride to activate the sllane in the Hiyama reaction and also serves as the reoxidant to convert Pd(0) to Pd(II) In the catalytic cycle.

  DOI：

  10.1021/ol202202a

文献信息

• Palladium-Catalyzed Direct C–H Arylation of Cyclic Enaminones with Aryl Iodides
  作者：Yi-Yun Yu、Lei Bi、Gunda I. Georg

  DOI：10.1021/jo400830t

  日期：2013.6.21

  A ligand-free method for the Pd-catalyzed direct arylation of cyclic enaminones using aryl iodides was developed. This method can be applied to a wide range of cyclic enaminones and aryl iodides with excellent C5-regioselectivity. Using widely available aryl iodides, the generality of this transformation provides easy access to a variety of 3-arylpiperidine structural motifs.

  开发了一种使用芳基碘对环烯胺酮进行 Pd 催化直接芳基化的无配体方法。该方法可应用于范围广泛的环状烯胺酮和芳基碘化物，并具有出色的 C5 区域选择性。使用广泛可用的芳基碘化物，这种转化的普遍性提供了对各种 3-芳基哌啶结构基序的轻松访问。
• Transition Metal-Free Direct Trifluoromethylation of 2,3-Dihydropyridin-4(1<i>H</i>)-ones at Room Temperature
  作者：Yi-Yun Yu、Adwait R. Ranade、Gunda I. Georg

  DOI：10.1002/adsc.201400417

  日期：2014.11.24

  AbstractA transition metal‐free, regioselective C‐5 trifluoromethylation of 2,3‐dihydropyridin‐4(1H)‐ones (cyclic enaminones) with trimethyl(trifluoromethyl)silane (TMSCF3) was developed that proceeds under mild conditions at room temperature. This direct transformation was successful with both electron‐rich and electron‐deficient cyclic enaminones. This method bypasses substrate prefunctionalization and transition metal catalysis, and allows the convenient and direct access to a variety of medicinally important 3‐trifluoromethylpiperidine derivatives. This chemistry also represents a rare example of a direct trifluoromethylation of an internal olefinic CH bond. A radical mechanism is proposed for this reaction.magnified image
• Direct Hiyama Cross-Coupling of Enaminones With Triethoxy(aryl)silanes and Dimethylphenylsilanol
  作者：Lei Bi、Gunda I. Georg

  DOI：10.1021/ol202202a

  日期：2011.10.21

  2,3-Dihydropyridin-4(1H)-ones undergo direct C-H functionalization at C5 In the palladium(II)-catalyzed Hiyama reaction, using triethoxy(aryl)silanes and dimethylphenylsilanol. The reagent CuF2 has a dual role In the reactions with triethoxy(aryl)silanes. It Is a source of fluoride to activate the sllane in the Hiyama reaction and also serves as the reoxidant to convert Pd(0) to Pd(II) In the catalytic cycle.