ethyl (3S)-2-(benzhydrylideneamino)-3-(hydroxymethyl)pent-4-enoate | 928259-87-4

• 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: ethyl (3S)-2-(benzhydrylideneamino)-3-(hydroxymethyl)pent-4-enoate
• CAS: 928259-87-4
• 化学式: C₂₁H₂₃NO₃
• 分子量: 337.419
• InChiKey: VIGNEHGFDJXYAS-QRIPLOBPSA-N

物化性质

• 沸点：
  458.7±45.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  58.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (3S)-2-(benzhydrylideneamino)-3-(hydroxymethyl)pent-4-enoate 在 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (1R,2S)-1-氨基-2-乙烯基环丙烷甲酸甲酯
  参考文献：
  名称：

  Catalytic asymmetric synthesis of ethyl (1R,2S)-dehydrocoronamate

  摘要：

  A synthesis of (1R,2S)-dehydrocoronamic acid ethyl ester was developed employing a regio- and enantioselective palladium-catalysed nucleophilic ring-opening of 3,4-epoxy-1-butene with a glycine anion equivalent as the key enantiodifferentiating step. The desired selectivity was achieved using Trost's naphthyl ligand. The subsequent activation of the free hydroxyl group and ring-closure by intramolecular S(N)2 reaction gave the desired amino acid ethyl ester. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.12.025
• 作为产物：
  描述：

  环氧丁烯 、 二苯亚甲基甘氨酸乙酯 在 bis(η3-allyl-μ-chloropalladium(II)) (S,S)-Trost's naphthyl 作用下， 以 二氯甲烷 为溶剂， 生成 ethyl (3S)-2-(benzhydrylideneamino)-3-(hydroxymethyl)pent-4-enoate 、
  参考文献：
  名称：

  Catalytic asymmetric synthesis of ethyl (1R,2S)-dehydrocoronamate

  摘要：

  A synthesis of (1R,2S)-dehydrocoronamic acid ethyl ester was developed employing a regio- and enantioselective palladium-catalysed nucleophilic ring-opening of 3,4-epoxy-1-butene with a glycine anion equivalent as the key enantiodifferentiating step. The desired selectivity was achieved using Trost's naphthyl ligand. The subsequent activation of the free hydroxyl group and ring-closure by intramolecular S(N)2 reaction gave the desired amino acid ethyl ester. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.12.025

文献信息

• Catalytic asymmetric synthesis of ethyl (1R,2S)-dehydrocoronamate
  作者：Martin E. Fox、Ian C. Lennon、Vittorio Farina

  DOI：10.1016/j.tetlet.2006.12.025

  日期：2007.2

  A synthesis of (1R,2S)-dehydrocoronamic acid ethyl ester was developed employing a regio- and enantioselective palladium-catalysed nucleophilic ring-opening of 3,4-epoxy-1-butene with a glycine anion equivalent as the key enantiodifferentiating step. The desired selectivity was achieved using Trost's naphthyl ligand. The subsequent activation of the free hydroxyl group and ring-closure by intramolecular S(N)2 reaction gave the desired amino acid ethyl ester. (c) 2006 Elsevier Ltd. All rights reserved.