(tert-butyl-diphenylsilanyloxy)acetaldehyde oxime | 735317-36-9

• 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: (tert-butyl-diphenylsilanyloxy)acetaldehyde oxime
• 英文别名: N-[2-[tert-butyl(diphenyl)silyl]oxyethylidene]hydroxylamine
• CAS: 735317-36-9
• 化学式: C₁₈H₂₃NO₂Si
• 分子量: 313.472
• InChiKey: ADYWAGQOPRXZQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.02
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  41.82
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (tert-butyl-diphenylsilanyloxy)acetaldehyde oxime 在 4-二甲氨基吡啶 、 次氯酸叔丁酯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 37.0h， 生成 Benzoic acid (R)-1-[(4S,5R)-3-(tert-butyl-diphenyl-silanyloxymethyl)-4-methyl-4,5-dihydro-isoxazol-5-yl]-ethyl ester
  参考文献：
  名称：

  Stereochemically Rich Pentaketides from Bis(isoxazolines):  A General Strategy for Efficient Polyketide Synthesis

  摘要：

  A strategy based on diastereoselective dipolar cycloaddition reaction of nitrile oxides and allylic alcoholates has been applied to the synthesis of bis(isoxazolines) that are precursors to polyketide fragments. These intermediates can be elaborated into protected polyols by chemoselective reductive opening of each isoxazoline sequentially or, alternatively, both simultaneously, potentially providing access to all stereoisomers of this carbon skeleton.

  DOI：

  10.1021/ol0490633
• 作为产物：
  描述：

  3-(tert-butyldiphenylsilyloxy)prop-1-ene 在 potassium osmate(VI) 、 sodium periodate 、 N-甲基吲哚酮 、 盐酸羟胺 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 水 、 叔丁醇 为溶剂， 反应 30.0h， 生成 (tert-butyl-diphenylsilanyloxy)acetaldehyde oxime
  参考文献：
  名称：

  Stereochemically Rich Pentaketides from Bis(isoxazolines):  A General Strategy for Efficient Polyketide Synthesis

  摘要：

  A strategy based on diastereoselective dipolar cycloaddition reaction of nitrile oxides and allylic alcoholates has been applied to the synthesis of bis(isoxazolines) that are precursors to polyketide fragments. These intermediates can be elaborated into protected polyols by chemoselective reductive opening of each isoxazoline sequentially or, alternatively, both simultaneously, potentially providing access to all stereoisomers of this carbon skeleton.

  DOI：

  10.1021/ol0490633

文献信息

• Polyketide Building Blocks via Diastereoselective Nitrile Oxide Cycloadditions with Homoallylic Alcohols and Monoprotected Homoallylic Diols
  作者：Nina Lohse-Fraefel、Erick M. Carreira

  DOI：10.1002/chem.200900529

  日期：2009.11.9

  hydroxyl‐directed method allows for the diastereoselective access to a wide variety of masked β‐hydroxy ketones, starting from readily available aliphatic and aromatic oximes, homoallylic alcohols and monoprotected homoallylic diols. The utility of the prepared Δ2‐isoxazolines as polyketide building blocks is demonstrated by their ready conversion into the corresponding β‐hydroxy ketones. The anti‐

  一种模块化的方法来Δ 2个-isoxazolines，潜醛醇加合物和聚酮化合物积木报道。镁介导的羟基定向方法允许非对映选择性地获得各种被掩盖的β-羟基酮，从容易获得的脂族和芳族肟，均丙醇和单保护均丙二醇开始。所制备的Δ的效用2个-isoxazolines如聚酮化合物结构单元是由它们易于转化成相应的β羟基酮证实。的抗反应-diastereoselectivity通过衍生化，NOE研究和已知化合物的比较成立。提出了观察到的非对映选择性的基本原理。