(Z)-N-<(2S,3S,4R)-2,3-O-isopropylidenedioxy-5-phenyl-4-(N-trifluoroacetoxybenzylamino)pentylidene>benzylamine N-oxide | 219586-67-1

• 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: (Z)-N-<(2S,3S,4R)-2,3-O-isopropylidenedioxy-5-phenyl-4-(N-trifluoroacetoxybenzylamino)pentylidene>benzylamine N-oxide
• 英文别名: N-benzyl-1-[(4S,5S)-5-[(1R)-1-[benzyl-(2,2,2-trifluoroacetyl)amino]-2-phenylethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methanimine oxide
• CAS: 219586-67-1
• 化学式: C₃₀H₃₁F₃N₂O₄
• 分子量: 540.582
• InChiKey: QXGLRVGZVWTCGC-JRUHLYRZSA-N

物化性质

• 沸点：
  718.8±60.0 °C(Predicted)
• 密度：
  1.251±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  39
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  67.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (Z)-N-<(2S,3S,4R)-2,3-O-isopropylidenedioxy-5-phenyl-4-(N-trifluoroacetoxybenzylamino)pentylidene>benzylamine N-oxide 在 sodium tetrahydroborate 、 copper diacetate 、 锌 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 25.0h， 生成 (2R,3S,4S,5R)-2,5-bis(phenylmethylamino)-3,4-O-isopropylidene-1,6-diphenyl-3,4-hexanediol
  参考文献：
  名称：

  Grignard Addition to Aldonitrones. Stereochemical Aspects and Application to the Synthesis of C₂-Symmetric Diamino Alcohols and Diamino Diols

  摘要：

  A new example of the stereoselective installation of the amino group at a saturated carbon center via organometallic addition of chiral aldehydes to nitrones is illustrated by the synthesis of 1,3-diamino propanol 1 and 1,4-diamino butandiol 2 units. Three diamino alcohol 1 stereotriads were obtained by stereoselective addition of alkylmagnesium halides (benzyl, cyclohexylmethyl, and metallyl) to the N-benzyl nitrones derived from beta-amino-alpha-hydroxy aldehydes followed by reduction of the resulting N-benzylhydroxylamines. Three 1,4-dibenzyl substituted stereoisomers of type 2 with fixed S configuration at C2 and C3 were prepared by sequential and simultaneous amination in two directions starting from L-threose nitrone and L-tartraldehyde bis-nitrone, respectively. The R,S,S,R isomer obtained by the former route was converted into a seven-membered ring cyclic urea (1,3-diazapin-2-one), i.e., a compound that belongs to a class of nonpeptide HIV-1 protease inhibitors.

  DOI：

  10.1021/jo980980u
• 作为产物：
  描述：

  在 草酰氯 、 magnesium sulfate 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (Z)-N-<(2S,3S,4R)-2,3-O-isopropylidenedioxy-5-phenyl-4-(N-trifluoroacetoxybenzylamino)pentylidene>benzylamine N-oxide
  参考文献：
  名称：

  Grignard Addition to Aldonitrones. Stereochemical Aspects and Application to the Synthesis of C₂-Symmetric Diamino Alcohols and Diamino Diols

  摘要：

  A new example of the stereoselective installation of the amino group at a saturated carbon center via organometallic addition of chiral aldehydes to nitrones is illustrated by the synthesis of 1,3-diamino propanol 1 and 1,4-diamino butandiol 2 units. Three diamino alcohol 1 stereotriads were obtained by stereoselective addition of alkylmagnesium halides (benzyl, cyclohexylmethyl, and metallyl) to the N-benzyl nitrones derived from beta-amino-alpha-hydroxy aldehydes followed by reduction of the resulting N-benzylhydroxylamines. Three 1,4-dibenzyl substituted stereoisomers of type 2 with fixed S configuration at C2 and C3 were prepared by sequential and simultaneous amination in two directions starting from L-threose nitrone and L-tartraldehyde bis-nitrone, respectively. The R,S,S,R isomer obtained by the former route was converted into a seven-membered ring cyclic urea (1,3-diazapin-2-one), i.e., a compound that belongs to a class of nonpeptide HIV-1 protease inhibitors.

  DOI：

  10.1021/jo980980u

文献信息

• Grignard Addition to Aldonitrones. Stereochemical Aspects and Application to the Synthesis of C₂-Symmetric Diamino Alcohols and Diamino Diols
  作者：Alessandro Dondoni、Daniela Perrone、Marilisa Rinaldi

  DOI：10.1021/jo980980u

  日期：1998.12.1

  A new example of the stereoselective installation of the amino group at a saturated carbon center via organometallic addition of chiral aldehydes to nitrones is illustrated by the synthesis of 1,3-diamino propanol 1 and 1,4-diamino butandiol 2 units. Three diamino alcohol 1 stereotriads were obtained by stereoselective addition of alkylmagnesium halides (benzyl, cyclohexylmethyl, and metallyl) to the N-benzyl nitrones derived from beta-amino-alpha-hydroxy aldehydes followed by reduction of the resulting N-benzylhydroxylamines. Three 1,4-dibenzyl substituted stereoisomers of type 2 with fixed S configuration at C2 and C3 were prepared by sequential and simultaneous amination in two directions starting from L-threose nitrone and L-tartraldehyde bis-nitrone, respectively. The R,S,S,R isomer obtained by the former route was converted into a seven-membered ring cyclic urea (1,3-diazapin-2-one), i.e., a compound that belongs to a class of nonpeptide HIV-1 protease inhibitors.