(1S)-N-benzyl-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-phenylmethanamine | 188200-12-6

• 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: (1S)-N-benzyl-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-phenylmethanamine
• CAS: 188200-12-6
• 化学式: C₁₉H₂₃NO₂
• 分子量: 297.397
• InChiKey: JYWURGOAESFUNH-MSOLQXFVSA-N

物化性质

• 沸点：
  400.9±30.0 °C(Predicted)
• 密度：
  1.084±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S)-N-benzyl-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-phenylmethanamine 在 palladium dihydroxide 氢气 、 三氟乙酸 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 27.0h， 生成 L-苯甘氨酸
  参考文献：
  名称：

  取决于O-保护基团，将溴化苯基镁加到衍生自R-甘油醛的N-苄基亚胺中的立体化学过程的逆转及其在合成苯基甘氨酸的两种对映异构体中的应用

  摘要：

  衍生自2，3-二-O-苄基-D-甘油醛和2，3-二-O-异亚丙基-D-甘油醛的N-苄基亚胺与苯基溴化镁反应，得到具有完全非对映选择性的完全保护的氨基二醇。加成反应的立体化学过程取决于O-保护基团的性质。这些化合物可以容易地转化为对映体纯的（R）和（S）α-苯基甘氨酸。

  DOI：

  10.1016/s0040-4020(96)01053-8
• 作为产物：
  描述：

  N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone 在 copper diacetate 、 氯化二乙基铝 、 溶剂黄146 、 锌 作用下， 反应 7.25h， 生成 (1S)-N-benzyl-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-phenylmethanamine
  参考文献：
  名称：

  Nucleophilic additions of Grignard reagents to N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone (BIGN). Synthesis of (2S,3R) and (2S,3S)-3-phenylisoserine

  摘要：

  A remarkable Lewis acid tuning has been observed in the nucleophilic addition of Grignard reagent to BIGN, the N-benzyl nitrone derived from 1,2-O-isopropylidene-D-glyceraldehyde. The obtained alpha,beta-dialkoxy hydroxylamines can serve as starting points for the synthesis of both aminodiols and alpha-hydroxy-beta-amino acids. This synthetic approach is illustrated by the synthesis of the antipode of the C-13 side chain of Taxotere as well as its C-3 epimer. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00741-8

文献信息

• Stereocontrolled addition of Grignard reagents to α-alkoxy nitrones. Synthesis of syn and anti 3-amino-1,2-diols
  作者：Pedro Merino、Elena Castillo、Francisco L Merchan、Tomas Tejero

  DOI：10.1016/s0957-4166(97)00175-4

  日期：1997.6

  The stereoselective addition of Grignard reagents to alpha-alkoxy nitrones has been achieved with excellent stereocontrol using ZnBr2 and Et2AlCl as precomplexing agents to obtain the corresponding syn- and anti- adducts, respectively. The obtained hydroxylamines have been transformed into valuable 3-amino-1,2-diols. (C) 1997 Elsevier Science Ltd.
• Reversal of the stereochemical course of the addition of phenylmagnesium bromide to N-benzylimines derived from R-glyceraldehyde depending on the O-protecting group and its application to the synthesis of both enantiomers of phenylglycine
  作者：Ramón Badorrey、Carlos Cativiela、María D. Díaz-de-Villegas、JoséA. Gálvez

  DOI：10.1016/s0040-4020(96)01053-8

  日期：1997.1

  The N-Benzyl imines derived from 2,3-di-O-benzyl-D-glyceraldehyde and 2,3-di-O-isopropylidene-D-glyceraldehyde reacted with phenylmagnesium bromide to afford fully protected aminodiols with total diastereoselectivity. The stereochemical course of the addition reaction depends on the nature of the O-protecting group. These compounds can be easily transformed to enantiomerically pure (R) and (S)α-phenylglycine

  衍生自2，3-二-O-苄基-D-甘油醛和2，3-二-O-异亚丙基-D-甘油醛的N-苄基亚胺与苯基溴化镁反应，得到具有完全非对映选择性的完全保护的氨基二醇。加成反应的立体化学过程取决于O-保护基团的性质。这些化合物可以容易地转化为对映体纯的（R）和（S）α-苯基甘氨酸。
• Nucleophilic additions of Grignard reagents to N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone (BIGN). Synthesis of (2S,3R) and (2S,3S)-3-phenylisoserine
  作者：Pedro Merino、Elena Castillo、Santiago Franco、Francisco L. Merchán、Tomas Tejero

  DOI：10.1016/s0040-4020(98)00741-8

  日期：1998.10

  A remarkable Lewis acid tuning has been observed in the nucleophilic addition of Grignard reagent to BIGN, the N-benzyl nitrone derived from 1,2-O-isopropylidene-D-glyceraldehyde. The obtained alpha,beta-dialkoxy hydroxylamines can serve as starting points for the synthesis of both aminodiols and alpha-hydroxy-beta-amino acids. This synthetic approach is illustrated by the synthesis of the antipode of the C-13 side chain of Taxotere as well as its C-3 epimer. (C) 1998 Elsevier Science Ltd. All rights reserved.