(Z)-2-fluoro-1-tris(trimethylsilyl)siloxyethene | 1332637-58-7

• 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: (Z)-2-fluoro-1-tris(trimethylsilyl)siloxyethene
• 英文别名: [(Z)-2-fluoroethenoxy]-tris(trimethylsilyl)silane
• CAS: 1332637-58-7
• 化学式: C₁₁H₂₉FOSi₄
• 分子量: 308.691
• InChiKey: YRLWZQJIEDGOBP-KHPPLWFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.64
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-2-fluoro-1-tris(trimethylsilyl)siloxyethene 在 sodium tetrahydroborate 、 1-[双(三氟甲烷磺酰基)甲基]-2,3,4,5,6-五氟苯 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成 (2RS,3SR)-2-fluoro-3-phenyl-3-[tris(trimethylsilyl)siloxy]propan-1-ol
  参考文献：
  名称：

  Rapid, One-Pot Synthesis of β-Siloxy-α-haloaldehydes

  摘要：

  The Mukaiyama cross-aldol reaction of alpha-fluoro-, alpha-chloro-, and alpha-bromoacetaldehyde-derived (Z)tris(trimethylsilyl)silyl enol ethers is described, furnishing anti-beta-siloxy-alpha-haloaldehydes. A highly diastereoselective, one-pot, sequential double-aldol process is developed, affording novel beta,delta-bissiloxy-alpha,gamma-bishaloaldehydes. Reactions are catalyzed by C(6)F(5)CHTf(2) and C(6)F(5)CTf(2)AlMe(2) (0.5-1.5 mol %) and provide access to halogenated polyketide fragments.

  DOI：

  10.1021/ja2066169
• 作为产物：
  描述：

  三(三甲基硅基)硅烷 在 正丁基锂 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (Z)-2-fluoro-1-tris(trimethylsilyl)siloxyethene
  参考文献：
  名称：

  Rapid, One-Pot Synthesis of β-Siloxy-α-haloaldehydes

  摘要：

  The Mukaiyama cross-aldol reaction of alpha-fluoro-, alpha-chloro-, and alpha-bromoacetaldehyde-derived (Z)tris(trimethylsilyl)silyl enol ethers is described, furnishing anti-beta-siloxy-alpha-haloaldehydes. A highly diastereoselective, one-pot, sequential double-aldol process is developed, affording novel beta,delta-bissiloxy-alpha,gamma-bishaloaldehydes. Reactions are catalyzed by C(6)F(5)CHTf(2) and C(6)F(5)CTf(2)AlMe(2) (0.5-1.5 mol %) and provide access to halogenated polyketide fragments.

  DOI：

  10.1021/ja2066169

文献信息

• β-Siloxy-α-haloketones through Highly Diastereoselective Single and Double Mukaiyama Aldol Reactions
  作者：Jakub Saadi、Hisashi Yamamoto

  DOI：10.1002/chem.201204493

  日期：2013.3.18

  Double‐action haloketones: A super silyl group enabled the first highly diastereoselective Mukaiyama aldol reactions of α‐chloro‐ and α‐fluoroketones with a wide range of aldehydes, providing anti‐β‐siloxy‐α‐haloketones. This process is compatible with one‐pot double‐aldol methodology and allows for rapid access to new halogen‐modified polyketide fragments bearing up to four contiguous stereocenters

  双作用卤代酮：超级甲硅烷基使α-氯代酮和α-氟代酮与多种醛发生首次高度非对映选择性Mukaiyama羟醛反应，从而提供反-β-甲硅烷氧基-α-卤代酮。该过程与一锅双羟醛方法兼容，并允许快速获得具有多达四个连续立体中心的新卤素改性聚酮化合物片段（参见方案）。
• Rapid, One-Pot Synthesis of β-Siloxy-α-haloaldehydes
  作者：Jakub Saadi、Matsujiro Akakura、Hisashi Yamamoto

  DOI：10.1021/ja2066169

  日期：2011.9.14

  The Mukaiyama cross-aldol reaction of alpha-fluoro-, alpha-chloro-, and alpha-bromoacetaldehyde-derived (Z)tris(trimethylsilyl)silyl enol ethers is described, furnishing anti-beta-siloxy-alpha-haloaldehydes. A highly diastereoselective, one-pot, sequential double-aldol process is developed, affording novel beta,delta-bissiloxy-alpha,gamma-bishaloaldehydes. Reactions are catalyzed by C(6)F(5)CHTf(2) and C(6)F(5)CTf(2)AlMe(2) (0.5-1.5 mol %) and provide access to halogenated polyketide fragments.