methyl (4R)-4-[benzyl(hydroxy)amino]-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]but-2-ynoate | 210415-78-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (4R)-4-[benzyl(hydroxy)amino]-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]but-2-ynoate
• CAS: 210415-78-4
• 化学式: C₁₇H₂₁NO₅
• 分子量: 319.357
• InChiKey: WZDZIYHASWLKTB-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  68.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (4R)-4-[benzyl(hydroxy)amino]-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]but-2-ynoate 在 palladium on activated charcoal 、 Lindlar's catalyst titanium(III) chloride 、 氨 、 氢气 、 sodium acetate 、 lithium 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 为溶剂， -35.0~25.0 ℃ 、98.06 kPa 条件下， 反应 25.75h， 生成 (R)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)pyrrolidin-2-one
  参考文献：
  名称：

  Ready access to enantiopure 5-substituted-3-pyrrolin-2-ones from N-benzyl-2,3-O-isopropylidene-d-glyceraldehyde nitrone (BIGN)

  摘要：

  The reaction of the lithiated salt of methyl propiolate with N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone (BIGN) afforded the corresponding propargyl hydroxylamines in a stereocontrolled way depending on the nature of the Lewis acid used as an additive. Subsequent reduction of the obtained hydroxylamines provided chiral 5-substituted-3-pyrrolin-2-ones, in high overall yields. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00150-5
• 作为产物：
  描述：

  N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone 、 丙炔酸甲酯 在 正丁基锂 作用下， 生成 methyl (4R)-4-[benzyl(hydroxy)amino]-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]but-2-ynoate
  参考文献：
  名称：

  Ready access to enantiopure 5-substituted-3-pyrrolin-2-ones from N-benzyl-2,3-O-isopropylidene-d-glyceraldehyde nitrone (BIGN)

  摘要：

  The reaction of the lithiated salt of methyl propiolate with N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone (BIGN) afforded the corresponding propargyl hydroxylamines in a stereocontrolled way depending on the nature of the Lewis acid used as an additive. Subsequent reduction of the obtained hydroxylamines provided chiral 5-substituted-3-pyrrolin-2-ones, in high overall yields. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00150-5

文献信息

• Ready access to enantiopure 5-substituted-3-pyrrolin-2-ones from N-benzyl-2,3-O-isopropylidene-d-glyceraldehyde nitrone (BIGN)
  作者：Pedro Merino、Elena Castillo、Santiago Franco、Francisco L Merchan、Tomas Tejero

  DOI：10.1016/s0957-4166(98)00150-5

  日期：1998.5

  The reaction of the lithiated salt of methyl propiolate with N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone (BIGN) afforded the corresponding propargyl hydroxylamines in a stereocontrolled way depending on the nature of the Lewis acid used as an additive. Subsequent reduction of the obtained hydroxylamines provided chiral 5-substituted-3-pyrrolin-2-ones, in high overall yields. (C) 1998 Elsevier Science Ltd. All rights reserved.