Phenyl-triisopropylsilanyloxy-acetaldehyde | 306961-30-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Phenyl-triisopropylsilanyloxy-acetaldehyde
• 英文别名: 2-Phenyl-2-tri(propan-2-yl)silyloxyacetaldehyde
• CAS: 306961-30-8
• 化学式: C₁₇H₂₈O₂Si
• 分子量: 292.494
• InChiKey: NJMRRMJVNAWPAM-UHFFFAOYSA-N

物化性质

• 沸点：
  333.8±30.0 °C(Predicted)
• 密度：
  0.937±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.12
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 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：

  Phenyl-triisopropylsilanyloxy-acetaldehyde 在 magnesium sulfate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 4-N-benzylamino-5-phenyl-3-n-propyl-5-triisopropylsilyloxy-1-(trimethylsilyl)pent-1-yne
  参考文献：
  名称：

  Comparative Study of the Diastereoselective Addition of Allenyl Zinc Reagents to α-Alkoxy (or Silyloxy) Aldehydes and Imines. A Straightforward Synthesis of Amino Alcohols from Imines

  摘要：

  The addition of allenylzine bromides to or-chiral imines proceeds with very high diastereoselectivity. This result is in contrast with the addition to the corresponding aldehydes, leading to poor diastereoselectivity. The anti/anti adducts are explained by Felkin-Ahn and Gaudemar-Yamamoto models of the transition state.

  DOI：

  10.1021/jo005509r
• 作为产物：
  描述：

  Phenyl-triisopropylsilanyloxy-acetic acid ethyl ester 在 二异丁基氢化铝 作用下， 以 乙醚 为溶剂， 以95%的产率得到Phenyl-triisopropylsilanyloxy-acetaldehyde
  参考文献：
  名称：

  Comparative Study of the Diastereoselective Addition of Allenyl Zinc Reagents to α-Alkoxy (or Silyloxy) Aldehydes and Imines. A Straightforward Synthesis of Amino Alcohols from Imines

  摘要：

  The addition of allenylzine bromides to or-chiral imines proceeds with very high diastereoselectivity. This result is in contrast with the addition to the corresponding aldehydes, leading to poor diastereoselectivity. The anti/anti adducts are explained by Felkin-Ahn and Gaudemar-Yamamoto models of the transition state.

  DOI：

  10.1021/jo005509r

文献信息

• Brønsted acid-catalysed desilylative heterocyclisation to form substituted furans
  作者：Emily G. Babcock、Md. Shafiqur Rahman、James E. Taylor

  DOI：10.1039/d2ob01828d

  日期：——

  Heterocyclisation of tert-butyldimethylsilyl (TBS) protected γ-hydroxy-α,β-unsaturated ketones catalysed by para-toluenesulfonic acid (p-TSA) to form substituted furans is reported. The reaction proceeds under mild conditions at room temperature in methanol to give a range of furan products (21 examples, up to 98% yield). Mechanistic experiments suggest the reaction proceeds via in situ deprotection

  报道了由对甲苯磺酸 ( p -TSA) 催化的叔丁基二甲基甲硅烷基 (TBS) 保护的 γ-羟基-α,β-不饱和酮杂环化形成取代呋喃。反应在温和的条件下在室温下在甲醇中进行，得到一系列呋喃产物（21 个实例，高达 98% 的收率）。机理实验表明，反应通过原位脱保护进行，然后进行催化脱水杂环化。
• Unexpected 1,2 syn diastereoselectivity in the three-component ‘aza Sakurai–Hosomi’ reaction
  作者：Jean-René Ella-Menye、William Dobbs、Manuella Billet、Philippe Klotz、André Mann

  DOI：10.1016/j.tetlet.2005.01.077

  日期：2005.3

  The three-component 'aza Sakurai-Hosomi' reaction performed on (+/-) O-protected mandelic aldehydes provided the unexpected syn hydroxy homoallylamines 2 and 2d as the major adducts. An intramolecular chelated transition state via a hydrogen bond is proposed to explain this 1,2 syn diastereoselectivity. (C) 2005 Elsevier Ltd. All rights reserved.