N-benzyl-N-[(1S)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-trimethylsilylprop-2-ynyl]hydroxylamine | 181303-70-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-benzyl-N-[(1S)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-trimethylsilylprop-2-ynyl]hydroxylamine
• CAS: 181303-70-8
• 化学式: C₁₈H₂₇NO₃Si
• 分子量: 333.503
• InChiKey: NYLLELYPAHKWAI-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  41.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-benzyl-N-[(1S)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-trimethylsilylprop-2-ynyl]hydroxylamine 在 palladium dihydroxide 吡啶 、 ruthenium trichloride 、 sodium periodate 、 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 25.0 ℃ 、551.58 kPa 条件下， 反应 145.36h， 生成 methyl (2R)-2-[(tert-butylcarbonyl)amino]-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanoate
  参考文献：
  名称：

  Diastereoselective nucleophilic addition of acetylide to N-benzyl-2, nitrone (BIGN). Stereodivergent synthesis of β-hydroxy-α-(hydroxyamino)- and β-hydroxy-α-amino acids

  摘要：

  The stereocontrolled nucleophilic addition of lithium trimethylsilyl acetylide to the N-benzyl nitrone (BIGN) derived from 2,3-O-isopropylidene-D-glyceraldehyde, followed by oxidative cleavage of the ensuing propargyl hydroxylamines resulted in an efficient stereodivergent synthesis of fully protected epimeric N-hydroxy alpha-amino esters 8 and 13 as well as the corresponding cw-amino esters 9 and 14. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00438-2
• 作为产物：
  描述：

  (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛 在 氯化二乙基铝 、 magnesium sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 5.08h， 生成 N-benzyl-N-[(1S)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-trimethylsilylprop-2-ynyl]hydroxylamine
  参考文献：
  名称：

  Diastereoselective nucleophilic addition of acetylide to N-benzyl-2, nitrone (BIGN). Stereodivergent synthesis of β-hydroxy-α-(hydroxyamino)- and β-hydroxy-α-amino acids

  摘要：

  The stereocontrolled nucleophilic addition of lithium trimethylsilyl acetylide to the N-benzyl nitrone (BIGN) derived from 2,3-O-isopropylidene-D-glyceraldehyde, followed by oxidative cleavage of the ensuing propargyl hydroxylamines resulted in an efficient stereodivergent synthesis of fully protected epimeric N-hydroxy alpha-amino esters 8 and 13 as well as the corresponding cw-amino esters 9 and 14. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00438-2

文献信息

• Direct vinylation and ethynylation of nitrones. Stereodivergent synthesis of allyl and propargyl amines
  作者：Pedro Merino、Sonia Anoro、Elena Castillo、Francisco Merchan、Tomas Tejero

  DOI：10.1016/0957-4166(96)00222-4

  日期：1996.7

  The addition of vinyl and ethynyl organometallic reagents to the nitrone derived from D-glyceraldehyde affords allyl and propargyl hydroxylamines which are easily converted into the corresponding allyl and propargyl amines. The stereoselectivity of the addition step can be controlled by the presence (or absence) of diethyl aluminium chloride.

  将乙烯基和乙炔基有机金属试剂加到衍生自D-甘油醛的硝酮中得到烯丙基和炔丙基羟胺，它们很容易转化为相应的烯丙基和炔丙基胺。加成步骤的立体选择性可以通过二乙基氯化铝的存在（或不存在）来控制。
• Diastereoselective nucleophilic addition of acetylide to N-benzyl-2, nitrone (BIGN). Stereodivergent synthesis of β-hydroxy-α-(hydroxyamino)- and β-hydroxy-α-amino acids
  作者：Pedro Merino、Santiago Franco、Francisco L. Merchan、Tomas Tejero

  DOI：10.1016/s0957-4166(97)00438-2

  日期：1997.10

  The stereocontrolled nucleophilic addition of lithium trimethylsilyl acetylide to the N-benzyl nitrone (BIGN) derived from 2,3-O-isopropylidene-D-glyceraldehyde, followed by oxidative cleavage of the ensuing propargyl hydroxylamines resulted in an efficient stereodivergent synthesis of fully protected epimeric N-hydroxy alpha-amino esters 8 and 13 as well as the corresponding cw-amino esters 9 and 14. (C) 1997 Published by Elsevier Science Ltd.