methyl (1R,2S,3S,4S)-3-phenylbicyclo[2.2.1]hept-5-ene-2-carboxylate | 130794-09-1

• 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 (1R,2S,3S,4S)-3-phenylbicyclo[2.2.1]hept-5-ene-2-carboxylate
• CAS: 130794-09-1
• 化学式: C₁₅H₁₆O₂
• 分子量: 228.291
• InChiKey: MJLYTZMVSKHETJ-RFGFWPKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  endo-5-carboxy-exo-6-phenylbicyclo<2.2.1>hept-2-ene 在 三乙胺 作用下， 以 乙腈 为溶剂， 生成 methyl (1R,2S,3S,4S)-3-phenylbicyclo[2.2.1]hept-5-ene-2-carboxylate
  参考文献：
  名称：

  Resolution of Diels–Alder Adducts Using a Chiral Carbodiimide

  摘要：

  研究了从手性单环、双环和三环酸以及N,N′-双((S)-1-苯乙基)氨基甲烯基二酰亚胺制备的酰脲衍生物的可分离性与立体化学之间的关系。通过硅胶柱层析传统分离的非对映体在甲醇水解后转化为相应酸的光学纯甲基酯。

  DOI：

  10.1246/cl.1990.1009

文献信息

• Scalable and Highly Diastereo- and Enantioselective Catalytic Diels–Alder Reaction of α,β-Unsaturated Methyl Esters
  作者：Tim Gatzenmeier、Mathias Turberg、Diana Yepes、Youwei Xie、Frank Neese、Giovanni Bistoni、Benjamin List

  DOI：10.1021/jacs.8b07092

  日期：2018.10.10

  Despite tremendous advances in enantioselective catalysis of the Diels-Alder reaction, the use of simple α,β-unsaturated esters, one of the most abundant and useful class of dienophiles, is still severely limited in scope due to their low reactivity. We report here a catalytic asymmetric Diels-Alder methodology for a large variety of α,β-unsaturated methyl esters and different dienes based on extremely

  尽管在 Diels-Alder 反应的对映选择性催化方面取得了巨大进展，但简单的 α,β-不饱和酯（最丰富和最有用的亲双烯体之一）的使用范围仍然受到严重限制，因为它们的反应性低。我们在此报告了一种催化不对称 Diels-Alder 方法，用于基于极易反应的亚氨基二磷酰亚胺 (IDPi) 路易斯酸的多种 α,β-不饱和甲酯和不同的二烯。来自基于精确域的局部对自然轨道耦合簇 (DLPNO-CCSD(T)) 计算的机械见解使催化剂控制和立体化学结果合理化。
• Fe-BPsalan Complex-Catalyzed Asymmetric [4 + 2] Cycloaddition of Cyclopentadiene with α,β-Unsaturated Heterocycles
  作者：Kai-Ge Chen、Hao Lu、Yi-Ming Zhou、Xiao-Long Wan、Hao-Yang Wang、Zhen-Jiang Xu、Hai-Ming Guo、Chi-Ming Che

  DOI：10.1021/acs.joc.1c02798

  日期：2022.7.1

  An efficient iron-catalyzed asymmetric [4 + 2] cycloaddition of cyclopentadiene with α,β-unsaturated acyl imidazoles or 2-cinnamoylisoindoline-1,3-dione derivatives was developed to afford the addition products in high yield and selectivity. Interestingly, the absolute structures of the addition products were controlled by the auxiliaries via different coordination modes with the same type of catalyst

  开发了一种有效的铁催化不对称 [4 + 2] 环戊二烯与 α,β-不饱和酰基咪唑或 2-cinnamoylisoindoline-1,3-dione 衍生物的环加成反应，以高产率和选择性提供加成产物。有趣的是，加成产物的绝对结构由助剂通过不同的配位模式与相同类型的催化剂控制。
• α,β-Unsaturated 2-Acyl Imidazoles as a Practical Class of Dienophiles for the DNA-Based Catalytic Asymmetric Diels−Alder Reaction in Water
  作者：Arnold J. Boersma、Ben L. Feringa、Gerard Roelfes

  DOI：10.1021/ol7015274

  日期：2007.8.1

  alpha,beta-Unsaturated 2-acyl imidazoles are a novel and practical class of dienophiles for the DNA-based catalytic asymmetric Diels-Alder reaction in water. The Diels-Alder products are obtained with very high diastereoselectivities and enantioselectivities in the range of 83-98%. The catalytic reaction was performed on a 1.0 mmol scale, and the imidazole auxiliary was removed readily.