methyl 2-diazo-4-phenylheptanoate | 174355-24-9

• 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: methyl 2-diazo-4-phenylheptanoate
• 英文别名: Methyl 2-diazo-4-phenylheptanoate
• CAS: 174355-24-9
• 化学式: C₁₄H₁₈N₂O₂
• 分子量: 246.309
• InChiKey: SWHWYLSRBGSINH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  28.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-diazo-4-phenylheptanoate 在 lithium aluminium tetrahydride 、 辛酸铑 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.17h， 生成 ((1S,2S,4R)-2-Methyl-4-phenyl-cyclopentyl)-methanol
  参考文献：
  名称：

  Predicting the Diastereoselectivity of Rh-Mediated Intramolecular C−H Insertion

  摘要：

  Rhodium-mediated cyclization of the alpha-diazo ester 1 proceeds with high diastereoselectivity, to give the trisubstituted cyclopentane 5. A computational model (ZINDO and Molecular Mechanics) based on our current mechanistic understanding of the reaction is presented. This model correctly predicts the dominant diastereomer from the cyclization of 1 and the eight (Table 2) other alpha-diazo esters studied thus far.

  DOI：

  10.1021/ja9515213
• 作为产物：
  描述：

  苯乙酸乙酯 在 吡啶 、 甲醇 、 p-nitrobenzenesulfonyl azide 、 lithium aluminium tetrahydride 、 溴 、 sodium hydride 、 碳酸氢钠 、 臭氧 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 61.0h， 生成 methyl 2-diazo-4-phenylheptanoate
  参考文献：
  名称：

  Predicting the Diastereoselectivity of Rh-Mediated Intramolecular C−H Insertion

  摘要：

  Rhodium-mediated cyclization of the alpha-diazo ester 1 proceeds with high diastereoselectivity, to give the trisubstituted cyclopentane 5. A computational model (ZINDO and Molecular Mechanics) based on our current mechanistic understanding of the reaction is presented. This model correctly predicts the dominant diastereomer from the cyclization of 1 and the eight (Table 2) other alpha-diazo esters studied thus far.

  DOI：

  10.1021/ja9515213

文献信息

• Predicting the Diastereoselectivity of Rh-Mediated Intramolecular C−H Insertion
  作者：Douglass F. Taber、Kamfia K. You、Arnold L. Rheingold

  DOI：10.1021/ja9515213

  日期：1996.1.1

  Rhodium-mediated cyclization of the alpha-diazo ester 1 proceeds with high diastereoselectivity, to give the trisubstituted cyclopentane 5. A computational model (ZINDO and Molecular Mechanics) based on our current mechanistic understanding of the reaction is presented. This model correctly predicts the dominant diastereomer from the cyclization of 1 and the eight (Table 2) other alpha-diazo esters studied thus far.