4-[2-(4-Methoxy-phenyl)-ethyl]-6-methyl-heptanoic acid ethyl ester | 714957-49-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-[2-(4-Methoxy-phenyl)-ethyl]-6-methyl-heptanoic acid ethyl ester
• 英文别名: Ethyl 4-[2-(4-methoxyphenyl)ethyl]-6-methylheptanoate
• CAS: 714957-49-0
• 化学式: C₁₉H₃₀O₃
• 分子量: 306.445
• InChiKey: CAFIXBNRZDMIRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[2-(4-Methoxy-phenyl)-ethyl]-6-methyl-heptanoic acid ethyl ester 在 rhodium(II)-based catalyst 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 25.51h， 生成
  参考文献：
  名称：

  Cyclopentane Construction by Rh-Catalyzed Intramolecular C−H Insertion:  Relative Reactivity of a Range of Catalysts

  摘要：

  The preparation and Rh-mediated cyclization of the alpha-diazoester 1 are outlined, and its utility in determining the elements that contribute to the reactivity of the intermediate Rh-carbenoid is presented. The rate of disappearance of diazo ester 1 catalyzed by several representative Rh(II) complexes was determined. The observed relative rate constants for the reaction of the Rh(II) complexes with 1 varied over a range of >10(7). The reactivity of the Rh-carbenoid intermediate was explored using the ratio of the sum of (3 + 4 + 5) to 2 (cyclization vs elimination), the ratio of 3 to the sum of (4 + 5) (chemo selectivity), and the ratio of 4 to 5 (diastereoselectivity). It is striking that these four measures of reactivity were found to be independent of each other.

  DOI：

  10.1021/jo0303766
• 作为产物：
  描述：

  4-甲基-2-戊酮 在 palladium on activated charcoal 、 锌 吡啶 、 sodium tetrahydroborate 、 四溴化碳 、 氢气 、 三氯化铁 、 铜 、 对甲苯磺酸 、 三苯基膦 、 sodium iodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 丙酮 为溶剂， 反应 22.16h， 生成 4-[2-(4-Methoxy-phenyl)-ethyl]-6-methyl-heptanoic acid ethyl ester
  参考文献：
  名称：

  Cyclopentane Construction by Rh-Catalyzed Intramolecular C−H Insertion:  Relative Reactivity of a Range of Catalysts

  摘要：

  The preparation and Rh-mediated cyclization of the alpha-diazoester 1 are outlined, and its utility in determining the elements that contribute to the reactivity of the intermediate Rh-carbenoid is presented. The rate of disappearance of diazo ester 1 catalyzed by several representative Rh(II) complexes was determined. The observed relative rate constants for the reaction of the Rh(II) complexes with 1 varied over a range of >10(7). The reactivity of the Rh-carbenoid intermediate was explored using the ratio of the sum of (3 + 4 + 5) to 2 (cyclization vs elimination), the ratio of 3 to the sum of (4 + 5) (chemo selectivity), and the ratio of 4 to 5 (diastereoselectivity). It is striking that these four measures of reactivity were found to be independent of each other.

  DOI：

  10.1021/jo0303766

文献信息

• Cyclopentane Construction by Rh-Catalyzed Intramolecular C−H Insertion:  Relative Reactivity of a Range of Catalysts
  作者：Douglass F. Taber、Pramod V. Joshi

  DOI：10.1021/jo0303766

  日期：2004.6.1

  The preparation and Rh-mediated cyclization of the alpha-diazoester 1 are outlined, and its utility in determining the elements that contribute to the reactivity of the intermediate Rh-carbenoid is presented. The rate of disappearance of diazo ester 1 catalyzed by several representative Rh(II) complexes was determined. The observed relative rate constants for the reaction of the Rh(II) complexes with 1 varied over a range of >10(7). The reactivity of the Rh-carbenoid intermediate was explored using the ratio of the sum of (3 + 4 + 5) to 2 (cyclization vs elimination), the ratio of 3 to the sum of (4 + 5) (chemo selectivity), and the ratio of 4 to 5 (diastereoselectivity). It is striking that these four measures of reactivity were found to be independent of each other.