triethylsilyl 5-bromopentanoate | 438202-84-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: triethylsilyl 5-bromopentanoate
• CAS: 438202-84-7
• 化学式: C₁₁H₂₃BrO₂Si
• 分子量: 295.292
• InChiKey: RXXPDYSYFBHVNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  15
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  二乙胺 、 triethylsilyl 5-bromopentanoate 反应 5.0h， 以71%的产率得到triethylsilyl 5-diethylaminopentanoate
  参考文献：
  名称：

  Ring-Opening Iodo- and Bromosilation of Lactones for the Formation of Silyl Haloalkanoates

  摘要：

  Ring-opening halosilation of lactones with two types of reagents, Et3SiH/MeI(PdCl2) (1a) and Et3SiH/AllylBr(PdCl2) (1b), was studied. Cyclic esters such as gamma-butyrolactones, delta-valerolactone, and 6-hexanolide reacted with 1 equiv of la,b to give triethylsilyl omega-iodo- and omega-bromoalkanoates in good yields. Reaction of an acyclic ester, methyl benzoate, with la afforded triethylsilyl benzoate. O-Silyl-protected amino acids could be obtained by amination of the halosilation products, triethylsilyl omega-bromoalkanoates.

  DOI：

  10.1021/jo011153n
• 作为产物：
  描述：

  delta-戊内酯 、 三乙基硅烷 在 palladium dichloride 3-溴丙烯 作用下， 反应 12.0h， 以79%的产率得到triethylsilyl 5-bromopentanoate
  参考文献：
  名称：

  Selective synthesis of halosilanes from hydrosilanes and utilization for organic synthesis

  摘要：

  Selective synthesis of halosilanes has been examined. Various types of halosilanes and halohydrosilanes, such as R3SiX, R2SiHX, R2SiX2, RSiH2X, RSiHX2 (X = Cl, Br, F), were obtained by the reactions of the corresponding hydrosilanes with Cu(II)-based reagents selectively in high yields. This method could be also applied to the synthesis of chlorofluorosilanes and chlorohydrogermanes. On the other hand, iodo- and bromosilanes and germanes were obtained by Pd- or Ni-catalyzed hydride-halogen exchange reactions of hydrosilanes with alkyl or allyl halides. Their synthetic applications have been demonstrated by using iodo-and bromosilanes and chlorofluorosilanes. (C) 2003 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(03)00254-7

文献信息

• Ring-Opening Iodo- and Bromosilation of Lactones for the Formation of Silyl Haloalkanoates
  作者：Arihiro Iwata、Joji Ohshita、Heqing Tang、Atsutaka Kunai、Yasushi Yamamoto、Chinami Matui

  DOI：10.1021/jo011153n

  日期：2002.5.1

  Ring-opening halosilation of lactones with two types of reagents, Et3SiH/MeI(PdCl2) (1a) and Et3SiH/AllylBr(PdCl2) (1b), was studied. Cyclic esters such as gamma-butyrolactones, delta-valerolactone, and 6-hexanolide reacted with 1 equiv of la,b to give triethylsilyl omega-iodo- and omega-bromoalkanoates in good yields. Reaction of an acyclic ester, methyl benzoate, with la afforded triethylsilyl benzoate. O-Silyl-protected amino acids could be obtained by amination of the halosilation products, triethylsilyl omega-bromoalkanoates.
• Selective synthesis of halosilanes from hydrosilanes and utilization for organic synthesis
  作者：Atsutaka Kunai、Joji Ohshita

  DOI：10.1016/s0022-328x(03)00254-7

  日期：2003.11

  Selective synthesis of halosilanes has been examined. Various types of halosilanes and halohydrosilanes, such as R3SiX, R2SiHX, R2SiX2, RSiH2X, RSiHX2 (X = Cl, Br, F), were obtained by the reactions of the corresponding hydrosilanes with Cu(II)-based reagents selectively in high yields. This method could be also applied to the synthesis of chlorofluorosilanes and chlorohydrogermanes. On the other hand, iodo- and bromosilanes and germanes were obtained by Pd- or Ni-catalyzed hydride-halogen exchange reactions of hydrosilanes with alkyl or allyl halides. Their synthetic applications have been demonstrated by using iodo-and bromosilanes and chlorofluorosilanes. (C) 2003 Elsevier Science B.V. All rights reserved.