2-benzyloxycarbonylamino-2-methylhexa-3,4-dienoic acid methyl ester | 729603-59-2

• 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: 2-benzyloxycarbonylamino-2-methylhexa-3,4-dienoic acid methyl ester
• CAS: 729603-59-2
• 化学式: C₁₆H₁₉NO₄
• 分子量: 289.331
• InChiKey: LSKONKZQIMGLEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  68.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-benzyloxycarbonylamino-2-methylhexa-3,4-dienoic acid methyl ester 在 silver tetrafluoroborate 、 di(rhodium)tetracarbonyl dichloride 、 sodium hydride 、 三苯基膦 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0~40.0 ℃ 、101.33 kPa 条件下， 反应 1.0h， 生成 3,5,7-trimethyl-6-oxo-1,3,5,6-tetrahydro-[2]pyrindine-2,3-dicarboxylic acid 2-benzyl ester 3-methyl ester
  参考文献：
  名称：

  Allenes and Transition Metals:  A Diverging Approach to Heterocycles

  摘要：

  [GRAPHICS]An alkynyl allene has been converted to heterocycles possessing an alpha-alkylidene cyclopentenone, a 4-alkylidene cyclopentenone, or a cross-conjugated triene. Thus, a common intermediate has been converted to three structurally unique compounds by changing only the reaction conditions and, therefore, controlling various reaction pathways.

  DOI：

  10.1021/ol0492391
• 作为产物：
  描述：

  N-CBZ-DL-丙氨酸 在 4-二甲氨基吡啶 、 正丁基锂 、 phosphate buffer 、 四丁基氟化铵 、 potassium hydrogencarbonate 、 二异丙胺 、 N,N'-二环己基碳二亚胺 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 2-benzyloxycarbonylamino-2-methylhexa-3,4-dienoic acid methyl ester
  参考文献：
  名称：

  Allenes and Transition Metals:  A Diverging Approach to Heterocycles

  摘要：

  [GRAPHICS]An alkynyl allene has been converted to heterocycles possessing an alpha-alkylidene cyclopentenone, a 4-alkylidene cyclopentenone, or a cross-conjugated triene. Thus, a common intermediate has been converted to three structurally unique compounds by changing only the reaction conditions and, therefore, controlling various reaction pathways.

  DOI：

  10.1021/ol0492391

文献信息

• Rhodium(I)-Catalyzed Ene-Allene Carbocyclization Strategy for the Formation of Azepines and Oxepines
  作者：Kay M. Brummond、Hongfeng Chen、Branko Mitasev、Anthony D. Casarez

  DOI：10.1021/ol049390a

  日期：2004.6.1

  A novel strategy for the preparation of seven-membered heterocyclic compounds has been realized. Treatment of ene-allene 1 with a catalytic quantity of rhodium biscarbonyl chloride dimer affords the cyclization product 2 in moderate to high yields. The scope and limitations of this new method are currently under investigation, and the results obtained to date are discussed within.
• Allenes and Transition Metals:  A Diverging Approach to Heterocycles
  作者：Kay M. Brummond、Branko Mitasev

  DOI：10.1021/ol0492391

  日期：2004.6.1

  [GRAPHICS]An alkynyl allene has been converted to heterocycles possessing an alpha-alkylidene cyclopentenone, a 4-alkylidene cyclopentenone, or a cross-conjugated triene. Thus, a common intermediate has been converted to three structurally unique compounds by changing only the reaction conditions and, therefore, controlling various reaction pathways.