N-((1S,2S)-6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl-1,2-d2)acetamide | 1426931-48-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: N-((1S,2S)-6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl-1,2-d2)acetamide
• CAS: 1426931-48-7
• 化学式: C₁₃H₁₇NO₂
• 分子量: 221.268
• InChiKey: OWBFSUWAUCHXEM-MEFDTAOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.69
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  6-甲氧基-3,4-二氢-1H-2-萘酮 在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 对甲苯磺酸 、 氘 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 20.0 ℃ 、2.03 MPa 条件下， 反应 41.0h， 生成 N-((1S,2S)-6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl-1,2-d2)acetamide 、
  参考文献：
  名称：

  Rhodium Phosphine–Phosphite Catalysts in the Hydrogenation of Challenging N-(3,4-dihydronaphthalen-2-yl) Amide Derivatives

  摘要：

  The enantioselective catalytic hydrogenation of N-(3,4-dihydronaphthalen-2-yl) amides (1) with rhodium catalysts bearing phosphine-phosphite ligands 4 has been studied. A wide catalyst screening, facilitated by the modular structure of 4, has found a highly enantioselective catalyst for this reaction. This catalyst gives a 93% ee in the hydrogenation of la and also produces high enantioselectivities, ranging from 83 to 93% ee, in the hydrogenation of several OMe- and Br- substituted substrates. In contrast, the structurally related enol esters 2 are very reluctant to undergo hydrogenation. A coordination study of the representative enamide Id has shown an unusual eta(6)-arene coordination mode, over the typical O,C,C chelating mode for enamides, as the preferred one for this substrate in a Rh(I) complex. Deuteration reactions of 1c,d indicate a clean syn addition of deuterium to the double bond without an isotopic effect on the enantioselectivity.

  DOI：

  10.1021/jo400345v