Benzyl-[2-(tert-butyl-dimethyl-silanyloxy)-prop-(Z)-ylidene]-amine | 152507-77-2

• 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: Benzyl-[2-(tert-butyl-dimethyl-silanyloxy)-prop-(Z)-ylidene]-amine
• 英文别名: N-benzyl-2-[tert-butyl(dimethyl)silyl]oxypropan-1-imine
• CAS: 152507-77-2
• 化学式: C₁₆H₂₇NOSi
• 分子量: 277.482
• InChiKey: RAIKUTUYMLJPTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.67
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Benzyl-[2-(tert-butyl-dimethyl-silanyloxy)-prop-(Z)-ylidene]-amine 在 盐酸 、 HF*(NEt₃)3 、 水 、 仲丁基锂 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 乙腈 为溶剂， 反应 6.0h， 生成 (2S,3S,4R)-3-Benzylamino-hex-5-yne-2,4-diol
  参考文献：
  名称：

  A Configurationally Stable Alkoxy Allenyl Zinc Reagent, en Route to anti-anti Vicinal Amino Diols

  摘要：

  [GRAPHICS]The reaction of an alkoxyallenyl zinc reagent with benzyl imines derived from lactic and mandelic acids proceeds highly diastereoselectively and leads to 2-amino-1,3-diol derivatives with an anti-anti pattern.

  DOI：

  10.1021/ol015941a
• 作为产物：
  描述：

  2-tert-butyldimethylsilyloxypropanal 、 苄胺 在 magnesium sulfate 作用下， 以 甲苯 为溶剂， 生成 Benzyl-[2-(tert-butyl-dimethyl-silanyloxy)-prop-(Z)-ylidene]-amine
  参考文献：
  名称：

  A Configurationally Stable Alkoxy Allenyl Zinc Reagent, en Route to anti-anti Vicinal Amino Diols

  摘要：

  [GRAPHICS]The reaction of an alkoxyallenyl zinc reagent with benzyl imines derived from lactic and mandelic acids proceeds highly diastereoselectively and leads to 2-amino-1,3-diol derivatives with an anti-anti pattern.

  DOI：

  10.1021/ol015941a

文献信息

• 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
  作者：Jean-François Poisson、Jean F. Normant

  DOI：10.1021/jo005509r

  日期：2000.10.1

  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.
• A Configurationally Stable Alkoxy Allenyl Zinc Reagent, en Route to <i>a</i><i>nti</i>-<i>a</i><i>nti</i> Vicinal Amino Diols
  作者：Jean-François Poisson、Jean F. Normant

  DOI：10.1021/ol015941a

  日期：2001.6.1

  [GRAPHICS]The reaction of an alkoxyallenyl zinc reagent with benzyl imines derived from lactic and mandelic acids proceeds highly diastereoselectively and leads to 2-amino-1,3-diol derivatives with an anti-anti pattern.