bromofluoroketene ethyl trimethylsilyl acetal | 207281-34-3

• 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: bromofluoroketene ethyl trimethylsilyl acetal
• 英文别名: (2-Bromo-1-ethoxy-2-fluoroethenoxy)-trimethylsilane
• CAS: 207281-34-3
• 化学式: C₇H₁₄BrFO₂Si
• 分子量: 257.175
• InChiKey: HPIDBBGRBBDFHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苄氧基乙醛 、 bromofluoroketene ethyl trimethylsilyl acetal 在 Masamune's catalyst 作用下， 以 various solvent(s) 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Enantioselective aldol reaction with a bromofluoroketene silyl acetal catalyzed by a chiral Lewis acid

  摘要：

  Bromofluoroketene silyl acetal 1 was prepared in pure form. Aldol reactions of 1 with achiral aldehydes catalyzed by chiral Lewis acid 2 proceeded with high enantioselectivity to give optically active syn- and anti-alpha-bromo-alpha-fluoro-beta-hydroxy esters 3a-h, respectively (up to 99% ee). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01717-6
• 作为产物：
  描述：

  三甲基氯硅烷 、 二溴氟乙酸乙酯 在 锌 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 bromofluoroketene ethyl trimethylsilyl acetal
  参考文献：
  名称：

  Enantioselective aldol reaction with a bromofluoroketene silyl acetal catalyzed by a chiral Lewis acid

  摘要：

  Bromofluoroketene silyl acetal 1 was prepared in pure form. Aldol reactions of 1 with achiral aldehydes catalyzed by chiral Lewis acid 2 proceeded with high enantioselectivity to give optically active syn- and anti-alpha-bromo-alpha-fluoro-beta-hydroxy esters 3a-h, respectively (up to 99% ee). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01717-6

文献信息

• Enantio- and Diastereoselective Synthesis of anti-α-Bromo-α-fluoro-β-hydroxycarbonylates
  作者：Katsuhiko Iseki、Yoshichika Kuroki、Yoshiro Kobayashi

  DOI：10.1055/s-1998-1677

  日期：1998.4

  Reaction of aldehydes with bromofluoroketene silyl acetal 1 in the presence of 20 mol% chiral Lewis acid 2 proceeds with enantio- and diastereoselectivities at -20 °C to afford optically active anti-α-bromo-α-fluoro-β-hydroxy esters 3a-f (up to 89:11 anti:syn, up to 93% ee).

  在 20 mol% 手性路易斯酸 2 的存在下，醛与溴氟甲烯硅基乙缩醛 1 的反应在 -20 °C 下以对映和非对映选择性进行，得到光学活性的反δ-溴δ-氟δ-²-羟基酯 3a-f（反:合高达 89:11，ee 值高达 93%）。
• Enantioselective aldol reaction with bromofluoroketene silyl acetals
  作者：Katsuhiko Iseki、Yoshichika Kuroki、Yoshiro Kobayashi

  DOI：10.1016/s0040-4020(99)00005-8

  日期：1999.2

  The aldol reaction of aldehydes with bromofluoroketene ethyl trimethylsilyl acetal in the presence of a catalytic amount of a chiral Lewis acid at -78 degrees C provides a mixture of the corresponding syn- and anli-alpha-bromo-alpha-fluoro-beta-hydroxy esters with high enantioselectivities (up to 99% ee). Reaction temperature has a great influence on the stereoselectivity. The aldol reaction at -20 degrees C proceeds with high enantio- and diasteteoselectivities to preferentially afford the anti-aldols having opposite signs of optical rotation to those at -78 degrees C. (C) 1999 Elsevier Science Ltd. All rights reserved.