(S)-3-benzyl-10,10-dimethyl-3,4-diazatricyclo[5.2.1.0^1,5]decan-2-one | 865439-10-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (S)-3-benzyl-10,10-dimethyl-3,4-diazatricyclo[5.2.1.0^1,5]decan-2-one
• 英文别名: (1S,5R,7R)-3-benzyl-10,10-dimethyl-3,4-diazatricyclo[5.2.1.01,5]decan-2-one
• CAS: 865439-10-7
• 化学式: C₁₇H₂₂N₂O
• 分子量: 270.374
• InChiKey: ODYLSRZBHNWKDH-CPUCHLNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-3-benzyl-10,10-dimethyl-3,4-diazatricyclo[5.2.1.0^1,5]decan-2-one 、 反式肉桂醛 在 三氟甲磺酸 作用下， 以 硝基甲烷-d3 、 重水 为溶剂， 生成 (1S,5R,7R)-3-Benzyl-10,10-dimethyl-2-oxo-4-[(E)-3-phenyl-prop-2-en-(E)-ylidene]-3-aza-4-azonia-tricyclo[5.2.1.0^1,5]decane
  参考文献：
  名称：

  Mechanistic Studies of Hydrazide-Catalyzed Enantioselective Diels−Alder Reactions

  摘要：

  The mechanism of the enantioselective, hydrazide-catalyzed Diels-Alder cycloaddition was investigated in detail. Both the formation of the reactive iminium species and the hydrolysis of the product iminium intermediates were found to be extremely rapid, leaving the cycloaddition as the kinetically significant step. Mechanistic studies using NMR showed that a retro-Diels-Alder reaction occurred during the catalytic cycle, suggesting a thermodynamic component to the reaction.

  DOI：

  10.1021/jo060339p
• 作为产物：
  描述：

  (S)-(+)-酮基蒎酸 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 均三甲苯 为溶剂， 反应 15.0h， 生成 (S)-3-benzyl-10,10-dimethyl-3,4-diazatricyclo[5.2.1.0^1,5]decan-2-one
  参考文献：
  名称：

  使用酰肼催化剂的水对映选择性有机催化Diels-Alder反应。一种用于有机加速的新型脚手架。

  摘要：

  [反应：见正文]环状酰肼在Diels-Alder水溶液反应中起不对称有机催化剂的作用。酰肼在紧凑的樟脑衍生的骨架中用作催化机构，该骨架赋予环加成以面部选择性。动力学证据表明该反应涉及快速亚胺的形成。

  DOI：

  10.1021/ol051476w

文献信息

• Mechanistic Studies of Hydrazide-Catalyzed Enantioselective Diels−Alder Reactions
  作者：Mathieu Lemay、William W. Ogilvie

  DOI：10.1021/jo060339p

  日期：2006.6.1

  The mechanism of the enantioselective, hydrazide-catalyzed Diels-Alder cycloaddition was investigated in detail. Both the formation of the reactive iminium species and the hydrolysis of the product iminium intermediates were found to be extremely rapid, leaving the cycloaddition as the kinetically significant step. Mechanistic studies using NMR showed that a retro-Diels-Alder reaction occurred during the catalytic cycle, suggesting a thermodynamic component to the reaction.
• Aqueous Enantioselective Organocatalytic Diels−Alder Reactions Employing Hydrazide Catalysts. A New Scaffold for Organic Acceleration
  作者：Mathieu Lemay、William W. Ogilvie

  DOI：10.1021/ol051476w

  日期：2005.9.1

  [reaction: see text] Cyclic hydrazides function as asymmetric organocatalysts in aqueous Diels-Alder reactions. The hydrazide is employed as the catalytic machinery in a compact camphor-derived framework that imparts facial selectivity to the cycloadditions. Kinetic evidence suggests the reaction involves rapid iminium formation.

  [反应：见正文]环状酰肼在Diels-Alder水溶液反应中起不对称有机催化剂的作用。酰肼在紧凑的樟脑衍生的骨架中用作催化机构，该骨架赋予环加成以面部选择性。动力学证据表明该反应涉及快速亚胺的形成。