ethyl (E,4R)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-4-phenylbut-2-enoate | 257296-52-9

• 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: ethyl (E,4R)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-4-phenylbut-2-enoate
• CAS: 257296-52-9
• 化学式: C₁₇H₂₃NO₄
• 分子量: 305.374
• InChiKey: SUHMJWZNDXROCO-GCZGRYASSA-N

物化性质

• 沸点：
  436.1±45.0 °C(Predicted)
• 密度：
  1.086±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：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (E,4R)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-4-phenylbut-2-enoate 在 吡啶 、 盐酸 、 四(三苯基膦)钯 、 三氟化硼乙醚 、 potassium carbonate 、 9-硼双环[3.3.1]壬烷 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 41.25h， 生成 (4S-trans)-4,5-dihydro-2,4-diphenyl-5-(2-hydroxyethyl)oxazoline
  参考文献：
  名称：

  Stereoselective Intramolecular Cyclization of Allyl and Homoallyl Benzamide via π-Allylpalladium Complex Catalyzed by Pd(0)

  摘要：

  The transformation of acyclic allylic benzamides 4 and homoallylic benzamides 12 to vinyl oxazolines 3 is achieved in the presence of base by the catalysis of Pd(0) in high yield and with high diastereoselectivity. Especially, in the case of homoallylic benzamides 12, trans-oxazolines 3 are formed exclusively or predominantly over cis-oxazolines 8, irrespective of the composition of their stereoisomers. The reaction is believed to proceed via the same pi-allylpalladium complex that arises from either primary or secondary allylic acetates. We applied this method to the syntheses of beta-amino-alpha-hydroxy acids 1 and gamma-amino-beta-hydroxy acids 2, conveniently protected as oxazoline.

  DOI：

  10.1021/jo991065r
• 作为产物：
  描述：

  (S)-(+)-2-(Boc-氨基)-2-苯基乙醇 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 2.5h， 生成 ethyl (E,4R)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-4-phenylbut-2-enoate
  参考文献：
  名称：

  Stereoselective Intramolecular Cyclization of Allyl and Homoallyl Benzamide via π-Allylpalladium Complex Catalyzed by Pd(0)

  摘要：

  The transformation of acyclic allylic benzamides 4 and homoallylic benzamides 12 to vinyl oxazolines 3 is achieved in the presence of base by the catalysis of Pd(0) in high yield and with high diastereoselectivity. Especially, in the case of homoallylic benzamides 12, trans-oxazolines 3 are formed exclusively or predominantly over cis-oxazolines 8, irrespective of the composition of their stereoisomers. The reaction is believed to proceed via the same pi-allylpalladium complex that arises from either primary or secondary allylic acetates. We applied this method to the syntheses of beta-amino-alpha-hydroxy acids 1 and gamma-amino-beta-hydroxy acids 2, conveniently protected as oxazoline.

  DOI：

  10.1021/jo991065r

文献信息

• Cyclization of <i>N</i>-Boc-(<i>E</i>)-α,β-unsaturated γ-amino acid active esters into <i>N</i>-Boc-(<i>Z</i>)-α,β-unsaturated γ-lactams through <i>E</i> → <i>Z</i> isomerization
  作者：Manjeet Singh、Manish Kumar、Sachin A. Nalawade、DRGKoppalu R. Puneeth Kumar、Hosahudya N. Gopi

  DOI：10.1039/d3ob00127j

  日期：——

  spontaneous transformation of the active esters of N-Boc protected E-α,β-unsaturated γ-amino acids into the corresponding Z-α,β-unsaturated γ-lactams with concomitant E → Z isomerization in the presence of a weak base. No cyclization was observed in the absence of the base. Analysis revealed that amide γ-NH is crucial for both lactamization and E → Z isomerization. This mild transformation provides easy

  在这里，我们报告了N -Boc 保护的E -α,β-不饱和 γ-氨基酸的活性酯自发转化为相应的Z -α,β-不饱和 γ-内酰胺，并伴随E → Z异构化弱基础。在没有碱的情况下没有观察到环化。分析表明，酰胺 γ-NH 对于内酰胺化和E → Z异构化都是至关重要的。这种温和的转变使合成具有挑战性的 α,β-不饱和 γ-内酰胺变得容易，也为双键的E → Z异构化提供了新的见解。
• Stereoselective Intramolecular Cyclization of Allyl and Homoallyl Benzamide via π-Allylpalladium Complex Catalyzed by Pd(0)
  作者：Kee-Young Lee、Yong-Hyun Kim、Min-Sung Park、Chang-Young Oh、Won-Hun Ham

  DOI：10.1021/jo991065r

  日期：1999.12.1

  The transformation of acyclic allylic benzamides 4 and homoallylic benzamides 12 to vinyl oxazolines 3 is achieved in the presence of base by the catalysis of Pd(0) in high yield and with high diastereoselectivity. Especially, in the case of homoallylic benzamides 12, trans-oxazolines 3 are formed exclusively or predominantly over cis-oxazolines 8, irrespective of the composition of their stereoisomers. The reaction is believed to proceed via the same pi-allylpalladium complex that arises from either primary or secondary allylic acetates. We applied this method to the syntheses of beta-amino-alpha-hydroxy acids 1 and gamma-amino-beta-hydroxy acids 2, conveniently protected as oxazoline.