2,2-Dimethyl-penta-3,4-dienyl-acetat | 19255-87-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,2-Dimethyl-penta-3,4-dienyl-acetat
• CAS: 19255-87-9
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: PMZGSMIHXGJNGM-UHFFFAOYSA-N

物化性质

• 沸点：
  193.4±10.0 °C(Predicted)
• 密度：
  0.884±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2-Dimethyl-penta-3,4-dienyl-acetat 、 (二甲基苯硅烷基)硼酸频那醇酯 在 catalyst:Pd(dba)2/R-1,1'-bina-2yl-P(3,5C₆H₃-Me₂)2 作用下， 以 甲苯 为溶剂， 以91%的产率得到(R)-5-acetoxy-3-(dimethylphenylsilyl)-4,4-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-pentene
  参考文献：
  名称：

  Palladium-Catalyzed Asymmetric Silaboration of Allenes

  摘要：

  An enantioselective silaboration of allenes was achieved using an achiral silylborane in the presence of a palladium catalyst bearing a chiral monodentate phosphine ligand. (R)-2-Bis(3,5-dimethylphenyl)phosphino-1,1'-binaphthyl gave the highest enantioselectivities in the addition of (diphenylmethylsilyl)pinacolborane to the internal C=C bond of terminal allenes at 0 degrees C, giving the corresponding beta-borylallylsilanes in high yields with high enantiomeric excesses. The enantioselectivity depended on the bulkiness of substituents of allenes: the enantiomeric excesses were found to be 91-93% ee (R = tert- and sec-alkyl), 88-90% ee (R = aryl), and 80-82% ee (R = prim-alkyl and Me) at 0 degrees C. Perfect chirality transfer was observed in the intramolecular cyclization reactions of the functionalized allylsilanes, affording highly enantioenriched cyclic alkenylboranes, which underwent Suzuki-Miyaura coupling with aryl halides.

  DOI：

  10.1021/ja063934h
• 作为产物：
  描述：

  2,2-二甲基戊-3,4-二烯醛 在 lithium aluminium tetrahydride 、 乙酸酐 作用下， 以 吡啶 、 乙醚 为溶剂， 生成 2,2-Dimethyl-penta-3,4-dienyl-acetat
  参考文献：
  名称：

  Unsaturated neopentyl compounds. Homoallenyl participation in the acetolysis of 2,2-dimethyl-3,4-pentadienyl p-bromobenzenesulfonate

  摘要：

  DOI：

  10.1021/ja01002a030

文献信息

• PALLADIUM-CATALYZED SYNTHESIS OF 2,3-DISUBSTITUTED ALLYLAMINES BY REGIOSELECTIVE AMINOPHENYLATION OR AMINOALKENYLATION OF 1,2-DIENES
  作者：Isao Shimizu、Jiro Tsuji

  DOI：10.1246/cl.1984.233

  日期：1984.2.5

  Reaction of 1,2-dienes, phenyl iodide or alkenyl bromides, and secondary amines in the presence of palladium-phosphine catalyst affords 2-phenyl or alkenyl allylic amines.

  在钯-膦催化剂存在下，1,2-二烯、苯基碘或烯基溴与二级胺反应生成2-苯基或烯基烯丙基胺。
• SHIMIZU, ISAO;TSUJI, JIRO, CHEM. LETT., 1984, N 2, 233-236
  作者：SHIMIZU, ISAO、TSUJI, JIRO

  DOI：——

  日期：——
• Unsaturated neopentyl compounds. Homoallenyl participation in the acetolysis of 2,2-dimethyl-3,4-pentadienyl p-bromobenzenesulfonate
  作者：Robert S. Bly、A. R. Ballentine、Soon Uoong. Koock

  DOI：10.1021/ja01002a030

  日期：1967.12
• Palladium-Catalyzed Asymmetric Silaboration of Allenes
  作者：Toshimichi Ohmura、Hiroki Taniguchi、Michinori Suginome

  DOI：10.1021/ja063934h

  日期：2006.10.1

  An enantioselective silaboration of allenes was achieved using an achiral silylborane in the presence of a palladium catalyst bearing a chiral monodentate phosphine ligand. (R)-2-Bis(3,5-dimethylphenyl)phosphino-1,1'-binaphthyl gave the highest enantioselectivities in the addition of (diphenylmethylsilyl)pinacolborane to the internal C=C bond of terminal allenes at 0 degrees C, giving the corresponding beta-borylallylsilanes in high yields with high enantiomeric excesses. The enantioselectivity depended on the bulkiness of substituents of allenes: the enantiomeric excesses were found to be 91-93% ee (R = tert- and sec-alkyl), 88-90% ee (R = aryl), and 80-82% ee (R = prim-alkyl and Me) at 0 degrees C. Perfect chirality transfer was observed in the intramolecular cyclization reactions of the functionalized allylsilanes, affording highly enantioenriched cyclic alkenylboranes, which underwent Suzuki-Miyaura coupling with aryl halides.