(Z,Z)-N,N-<(4S,5S)-2,2-dimethyl-4,5-dimethylethenyl-1,3-dioxolane>-bis(benzylamine N-oxide) | 207561-61-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z,Z)-N,N-<(4S,5S)-2,2-dimethyl-4,5-dimethylethenyl-1,3-dioxolane>-bis(benzylamine N-oxide)
• 英文别名: N-benzyl-1-[(4S,5S)-5-[(Z)-[benzyl(oxido)azaniumylidene]methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methanimine oxide
• CAS: 207561-61-3
• 化学式: C₂₁H₂₄N₂O₄
• 分子量: 368.433
• InChiKey: UPMNNLZPQNTWPD-UAHCAFNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  76
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z,Z)-N,N-<(4S,5S)-2,2-dimethyl-4,5-dimethylethenyl-1,3-dioxolane>-bis(benzylamine N-oxide) 、 苄基氯化镁 在 dimethylpropylene urea 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 (2S,3S,4S,5S)-2,5-bis(N-benzylhydroxylamine)-3,4-O-isopropylidene-1,6-diphenyl-3,4-hexanediol 、 (2R,3S,4S,5S)-2,5-bis(N-benzylhydroxylamine)-3,4-O-isopropylidene-1,6-diphenyl-3,4-hexanediol
  参考文献：
  名称：

  （S，S）-tar醛二硝基苯的立体选择性格氏加成反应合成C 2对称二苄基二氨基二醇。

  摘要：

  通过将苄基氯化镁双加到衍生自（R，R）-酒石醛的双硝基并还原生成的二羟胺来说明1,4-二氨基2,3-二醇的新的不对称二维合成。

  DOI：

  10.1016/s0040-4039(98)00330-x
• 作为产物：
  描述：

  (4R,5R)-4,5-二乙氧基羰基-2,2-二甲基二氧 、 N-苄基羟胺 在 二异丁基氢化铝 作用下， 生成 (Z,Z)-N,N-<(4S,5S)-2,2-dimethyl-4,5-dimethylethenyl-1,3-dioxolane>-bis(benzylamine N-oxide)
  参考文献：
  名称：

  （S，S）-tar醛二硝基苯的立体选择性格氏加成反应合成C 2对称二苄基二氨基二醇。

  摘要：

  通过将苄基氯化镁双加到衍生自（R，R）-酒石醛的双硝基并还原生成的二羟胺来说明1,4-二氨基2,3-二醇的新的不对称二维合成。

  DOI：

  10.1016/s0040-4039(98)00330-x

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.
• Synthesis of C2-symmetric dibenzyldiamino diols by double stereoselective grignard addition to (S,S)-tartraldehyde dinitrone
  作者：Alessandro Dondoni、Daniela Perrone、Marilisa Rinaldi

  DOI：10.1016/s0040-4039(98)00330-x

  日期：1998.4

  A new asymmetric two-dimensional synthesis of 1,4-diamino 2,3-diols is illustrated by double addition of benzylmagnesium chloride to the bis-nitrone derived from (R,R)-tartraldehyde and reduction of the resulting dihydroxylamines.

  通过将苄基氯化镁双加到衍生自（R，R）-酒石醛的双硝基并还原生成的二羟胺来说明1,4-二氨基2,3-二醇的新的不对称二维合成。