tert-butyl (E)-8-oxooct-2-enoate | 1352429-41-4

• 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: tert-butyl (E)-8-oxooct-2-enoate
• CAS: 1352429-41-4
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.289
• InChiKey: YERGNMWASYWYAP-VQHVLOKHSA-N

物化性质

• 沸点：
  289.3±23.0 °C(predicted)
• 密度：
  0.960±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (E)-8-oxooct-2-enoate 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 N-氯代丁二酰亚胺 、 正丁基锂 、 草酰氯 、 二甲基亚砜 、 二苯基氯化膦 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 45.5h， 生成 tert-butyl (2S,3R,αR)-2-acetoxy-3-[N-benzyl-N-(α-methylbenzyl)amino]-8,8-dichlorooctanoate
  参考文献：
  名称：

  Asymmetric syntheses of the N-terminal α-hydroxy-β-amino acid components of microginins 612, 646 and 680

  摘要：

  The asymmetric syntheses of the N-terminal alpha-hydroxy-beta-amino acid components of microginins 612, 646 and 680 are reported. Conjugate addition of lithium (R)-N-benzyl-N-(alpha-methylbenzyl)amide to the requisite (E)-alpha,beta-unsaturated ester followed by in situ enolate oxidation with (-)-(camphorsulfonyl)oxaziridne (CSO) gave the corresponding anti-alpha-hydroxy-beta-amino esters. Sequential Swern oxidation followed by diastereoselective reduction gave the corresponding syn-alpha-hydroxy-beta-amino esters. Subsequent N-debenzylation (i.e., hydrogenolysis for microginin 612, and NaBrO3-mediated oxidative N-debenzylation for microginins 646 and 680) followed by acid catalysed ester hydrolysis gave the corresponding syn-alpha-hydroxy-beta-amino acids, the N-terminal components of microginins 612, 646 and 680, in good yield. An analogous strategy for elaboration of the enantiopure anti-alpha-hydroxy-beta-amino esters facilitated the asymmetric synthesis of the corresponding C(2)-epimeric alpha-hydroxy-beta-amino acids. (C) 2017 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2017.09.022
• 作为产物：
  描述：

  环己烯 在 臭氧 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 生成 tert-butyl (E)-8-oxooct-2-enoate
  参考文献：
  名称：

  Asymmetric syntheses of the N-terminal α-hydroxy-β-amino acid components of microginins 612, 646 and 680

  摘要：

  The asymmetric syntheses of the N-terminal alpha-hydroxy-beta-amino acid components of microginins 612, 646 and 680 are reported. Conjugate addition of lithium (R)-N-benzyl-N-(alpha-methylbenzyl)amide to the requisite (E)-alpha,beta-unsaturated ester followed by in situ enolate oxidation with (-)-(camphorsulfonyl)oxaziridne (CSO) gave the corresponding anti-alpha-hydroxy-beta-amino esters. Sequential Swern oxidation followed by diastereoselective reduction gave the corresponding syn-alpha-hydroxy-beta-amino esters. Subsequent N-debenzylation (i.e., hydrogenolysis for microginin 612, and NaBrO3-mediated oxidative N-debenzylation for microginins 646 and 680) followed by acid catalysed ester hydrolysis gave the corresponding syn-alpha-hydroxy-beta-amino acids, the N-terminal components of microginins 612, 646 and 680, in good yield. An analogous strategy for elaboration of the enantiopure anti-alpha-hydroxy-beta-amino esters facilitated the asymmetric synthesis of the corresponding C(2)-epimeric alpha-hydroxy-beta-amino acids. (C) 2017 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2017.09.022

文献信息

• Asymmetric synthesis of piperidines and octahydroindolizines using a one-pot ring-closure/N-debenzylation procedure
  作者：Stephen G. Davies、Ai M. Fletcher、Deri G. Hughes、James A. Lee、Paul D. Price、Paul M. Roberts、Angela J. Russell、Andrew D. Smith、James E. Thomson、Oliver M.H. Williams

  DOI：10.1016/j.tet.2011.09.038

  日期：2011.12

  The conjugate addition of an enantiopure lithium amide to a zeta-hydroxy-alpha,beta-unsaturated ester followed by a one-pot ring-closure/N-debenzylation protocol has been used in the asymmetric syntheses of (S)coniine and (R)-delta-coniceine (isolated as the corresponding hydrochloride salts), and (R,R)-1-(hydroxymethyl)octahydroindolizine (the bicyclic fragment of stellettamides A-C). (C) 2011 Elsevier Ltd. All rights reserved.
• Asymmetric syntheses of the N-terminal α-hydroxy-β-amino acid components of microginins 612, 646 and 680
  作者：Stephen G. Davies、Ai M. Fletcher、Abigail R. Hanby、Paul M. Roberts、James E. Thomson

  DOI：10.1016/j.tetasy.2017.09.022

  日期：2017.12

  The asymmetric syntheses of the N-terminal alpha-hydroxy-beta-amino acid components of microginins 612, 646 and 680 are reported. Conjugate addition of lithium (R)-N-benzyl-N-(alpha-methylbenzyl)amide to the requisite (E)-alpha,beta-unsaturated ester followed by in situ enolate oxidation with (-)-(camphorsulfonyl)oxaziridne (CSO) gave the corresponding anti-alpha-hydroxy-beta-amino esters. Sequential Swern oxidation followed by diastereoselective reduction gave the corresponding syn-alpha-hydroxy-beta-amino esters. Subsequent N-debenzylation (i.e., hydrogenolysis for microginin 612, and NaBrO3-mediated oxidative N-debenzylation for microginins 646 and 680) followed by acid catalysed ester hydrolysis gave the corresponding syn-alpha-hydroxy-beta-amino acids, the N-terminal components of microginins 612, 646 and 680, in good yield. An analogous strategy for elaboration of the enantiopure anti-alpha-hydroxy-beta-amino esters facilitated the asymmetric synthesis of the corresponding C(2)-epimeric alpha-hydroxy-beta-amino acids. (C) 2017 Published by Elsevier Ltd.