triethylsilyl 6-bromohexanoate | 438202-86-9

• 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 6-bromohexanoate
• CAS: 438202-86-9
• 化学式: C₁₂H₂₅BrO₂Si
• 分子量: 309.319
• InChiKey: NLMZREGRQFVTPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.49
• 重原子数：
  16
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 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 6-bromohexanoate 反应 5.0h， 以73%的产率得到triethylsilyl 6-diethylaminohexanoate
  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
• 作为产物：
  描述：

  6-己内酯 、 三乙基硅烷 在 palladium dichloride 3-溴丙烯 作用下， 反应 12.0h， 以75%的产率得到triethylsilyl 6-bromohexanoate
  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

• Syntheses of Aldol Products and Cyanohydrins from Carboxylic Acids Using Hydrosilanes, Organosilicon Reagents, and Indium Triiodide Catalyst
  作者：Yoshihiro Inamoto、Yoshihiro Nishimoto、Makoto Yasuda、Akio Baba

  DOI：10.1246/cl.130790

  日期：2013.12.5

  Carboxylic acids were applied to an indium triiodide-catalyzed reductive aldol reaction and a reductive cyanation in order to produce aldol adducts and cyanohydrins, respectively, in which the separate addition of two kinds of hydrosilanes was crucial in combination with either ketene silyl acetals or silyl cyanides.

  羧酸在一碘化铟催化的还原性羟醛反应和还原氰化反应中分别被用来生成羟醛加合物和氰醇，其中两种不同硅氢试剂的分别添加与烯酮硅缩醛或硅基氰化物结合使用是至关重要的。
• 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.