3-((dimethylamino)methylene)-d-camphor | 113890-54-3

• 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: 3-((dimethylamino)methylene)-d-camphor
• 英文别名: 3-[(dimethylamino)methylene]-d-camphor
• CAS: 113890-54-3
• 化学式: C₁₃H₂₁NO
• 分子量: 207.316
• InChiKey: UGOSHQIMOIGOEZ-MFKMUULPSA-N

物化性质

• 沸点：
  277.7±19.0 °C(Predicted)
• 密度：
  1.058±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.46
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-((dimethylamino)methylene)-d-camphor 在 盐酸 、 palladium on activated charcoal 、 氢气 作用下， 以 乙醇 为溶剂， 以100 %的产率得到(1R,3Ξ)-3-dimethylaminomethyl-1,7,7-trimethyl-norbornan-2-one; hydrochloride
  参考文献：
  名称：

  Synthesis of Bifunctional Amine-Squaramide Organocatalysts Derived from 3-((Dimethylamino) methylene)camphor

  摘要：

  Four bifunctional, noncovalent amine-squaramide organocatalysts were prepared from camphor in five steps. The stereochemistry of the prepared catalysts was thoroughly analyzed using various spectroscopic techniques. Their organocatalytic activity was investigated in the Michael addition of acetylacetone to trans-β-nitrostyrene. The addition product was formed in complete conversion and with an enantioselectivity of up to 77% ee. In the reactions catalyzed by the 2-exo-3-endo catalysts, the major (S)-enantiomer was formed, whereas in the presence of 2-endo-3-endo catalysts, the (R)-enantiomer was formed as the major product.

  DOI：

  10.17344/acsi.2024.8757
• 作为产物：
  描述：

  白樟油 、 N,N,N',N',2,2-Hexamethylpropan-1,1-diamin 以 N,N-二甲基甲酰胺 为溶剂， 以83 %的产率得到3-((dimethylamino)methylene)-d-camphor
  参考文献：
  名称：

  Synthesis of Bifunctional Amine-Squaramide Organocatalysts Derived from 3-((Dimethylamino) methylene)camphor

  摘要：

  Four bifunctional, noncovalent amine-squaramide organocatalysts were prepared from camphor in five steps. The stereochemistry of the prepared catalysts was thoroughly analyzed using various spectroscopic techniques. Their organocatalytic activity was investigated in the Michael addition of acetylacetone to trans-β-nitrostyrene. The addition product was formed in complete conversion and with an enantioselectivity of up to 77% ee. In the reactions catalyzed by the 2-exo-3-endo catalysts, the major (S)-enantiomer was formed, whereas in the presence of 2-endo-3-endo catalysts, the (R)-enantiomer was formed as the major product.

  DOI：

  10.17344/acsi.2024.8757

文献信息

• Combinatorial Synthesis of Acacen-Type Ligands and Their Coordination Compounds
  作者：Urša Tomažin、Uroš Grošelj、Marta Počkaj、Franc Požgan、Bogdan Štefane、Jurij Svete

  DOI：10.1021/acscombsci.7b00027

  日期：2017.6.12

  transamination between six primary diamines and eight enaminones. The bis-enaminone products were used as tetradentate ligands for coordination of copper(II), nickel(II), cobalt(II), and palladium(II). Dependence of the preferred E- or Z-configuration of the enaminone ligand on the α-substituent of the enaminone moiety in solution was determined by NMR and confirmed by X-ray diffraction. The copper(II) complexes

  开发了一种高度模块化的合成方法，用于制备阿拉伯胶型配体及其配位化合物。通过在六个伯二胺和八个烯胺酮之间进行组合酸催化的氨基转移反应，合成了一系列46种acacen型配体。双烯胺产品用作四齿配体，用于配位铜（II），镍（II），钴（II）和钯（II）。通过NMR确定溶液中烯胺酮配体的优选E-或Z-构型对烯胺酮部分的α-取代基的依赖性，并通过X射线衍射证实。测试了铜（II）配合物在3 + 2偶氮甲亚胺亚胺成丙酸甲酯的环加成反应中作为催化剂的适用性。
• exo,endo-3-[(Dimethylamino)methyl]-d-camphor: d-camphor Mannich products
  作者：Natalie L. McClure、Gui Yuan Dai、Harry S. Mosher

  DOI：10.1021/jo00246a042

  日期：1988.5