(2R)-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde | 72203-35-1

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机氧化物
• 英文名称: (2R)-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde
• 英文别名: (1R,2R,4R)-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde；(R)-endo-bicyclo[2.2.2]oct-5-ene-2-carboxaldehyde；5-norbornene-2-carbaldehyde；2-Formyl-bicyclo[2.2.1]hepten-(5)
• CAS: 72203-35-1
• 化学式: C₈H₁₀O
• 分子量: 122.167
• InChiKey: AJIBZRIAUXVGQJ-CSMHCCOUSA-N

物化性质

• 沸点：
  182.2±29.0 °C(Predicted)
• 密度：
  1.162±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2R)-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde 以60%的产率得到
  参考文献：
  名称：

  VINOGRADOV, M. G.;TUZIKOV, A. B.;NIKISHIN, G. I., IZV. AN CCCP. CEP. XIM.,(1989) N1, S. 2565-2568

  摘要：

  DOI：
• 作为产物：
  描述：

  环戊二烯 以80%的产率得到
  参考文献：
  名称：

  Van de Weghe Pierre, Collin Jacqueline, Tetrahedron Lett, 35 (1994) N 16, S 2545-2548

  摘要：

  DOI：

文献信息

• Polyesters Containing Chiral Imidazolidinone Salts in Polymer Main Chain: Heterogeneous Organocatalysts for the Asymmetric Diels-Alder Reaction
  作者：Naoki Haraguchi、Thanh Liem Nguyen、Shinichi Itsuno

  DOI：10.1002/cctc.201700723

  日期：2017.10.10

  imidazolidinone salts incorporated into the polymer main chain. Main‐chain ionic polyesters functionalized with chiral imidazolidinone salts in the polymer main chain were synthesized by the neutralization polymerization of a chiral imidazolidinone dimer with selected aromatic disulfonic acids. These polyesters were used as heterogeneous organocatalysts in the asymmetric Diels–Alder reaction of trans‐cinnamaldehyde

  成功合成了用手性咪唑啉酮盐官能化的新型主链聚酯。带有两个羟基苯基的手性咪唑啉酮二聚体与选择的非手性二羧酸氯化物的缩聚反应，然后加入酸，得到的聚酯具有掺入聚合物主链中的手性咪唑啉酮盐。通过手性咪唑烷酮二聚体与所选芳香族二磺酸的中和聚合反应，合成了在聚合物主链中被手性咪唑烷酮盐官能化的主链离子聚酯。这些聚酯在反式的不对称Diels-Alder反应中用作多相有机催化剂。肉桂醛和1,3-环戊二烯。通过优化聚合物主链结构，可实现高达97％的对映选择性，这比使用相应的单体和二聚手性咪唑烷酮盐获得的对映选择性高。这些非均相有机催化剂易于从反应混合物中回收并重复使用几次，而对映选择性没有明显损失。
• Design of Brønsted Acid-Assisted Chiral Lewis Acid (BLA) Catalysts for Highly Enantioselective Diels−Alder Reactions
  作者：Kazuaki Ishihara、Hideki Kurihara、Masayuki Matsumoto、Hisashi Yamamoto

  DOI：10.1021/ja9810282

  日期：1998.7.1

  Bronsted acid-assisted chiral Lewis acid (BLA) was highly effective as a chiral catalyst for the enantioselective Diels−Alder reaction of both α-substituted and α-unsubstituted α,β-enals with various dienes. Hydroxy groups in optically active binaphthol derivatives and boron reagents with electron-withdrawing substituents were used as Bronsted acids and Lewis acids, respectively. Intramolecular Bronsted

  布朗斯台德酸辅助的手性路易斯酸 (BLA) 作为手性催化剂非常有效，可用于 α-取代和 α-未取代的 α,β-烯醛与各种二烯的对映选择性 Diels-Alder 反应。光学活性联萘酚衍生物中的羟基和具有吸电子取代基的硼试剂分别用作布朗斯台德酸和路易斯酸。手性 BLA 催化剂中的分子内布朗斯台德酸在加速 Diels-Alder 反应速率和产生高水平的对映选择性方面发挥了重要作用。特别是，由于手性 BLA 催化剂中羟基芳基在过渡态组装中的分子内氢键相互作用和有吸引力的 π-π 供体-受体相互作用，实现了优异的对映选择性。
• Immobilization of MacMillan Imidazolidinone as Mac-SILC and its Catalytic Performance on Sustainable Enantioselective Diels-Alder Cycloaddition
  作者：Hisahiro Hagiwara、Toshihiro Kuroda、Takashi Hoshi、Toshio Suzuki

  DOI：10.1002/adsc.200900865

  日期：2010.3.22

  (Mac‐SILC) in the pores of silica gel with the aid of an ionic liquid – 1‐butyl‐3‐methylimidazolium bis(trifluoromethylsulfonyl)imide. The heterogenized organocatalyst was utilized for the enantioselective Diels–Alder reaction of cyclopentadiene and cinnamaldehyde, recovered by simple filtration and subsequent evacuation, and repeatedly used up to six times in 81% average chemical yield, 87% ee for endo‐

  麦克米伦的咪唑啉酮催化剂作为负载型离子液体催化剂（Mac‐SILC）借助离子液体– 1-丁基-3-甲基咪唑双（三氟甲基磺酰基）酰亚胺固定在硅胶孔中。所述多相有机催化剂是用于环戊二烯与肉桂醛的对映选择性狄尔斯-阿尔德反应，回收通过简单过滤和随后的抽空，并重复使用多达六次在81％的平均化学产率，87％ee值用于内切-和80％ee值用于exo产品。Mac‐SILC对多种基材均有效。
• Asymmetric Organocatalytic Diels–Alder Reactions on Solid Support
  作者：Sami A. Selkälä、Jan Tois、Petri M. Pihko、Ari M. P. Koskinen

  DOI：10.1002/1615-4169(200210)344:9<941::aid-adsc941>3.0.co;2-m

  日期：2002.10

  Asymmetric organocatalysis on solid support combines the environmental advantages of metal-free catalysts and the ease of operation of solid-supported reagents. Enantioselective organocatalytic DielsAlder reactions have been demonstrated by two different solid-supported chiral organocatalysts. The catalysts are easy to recover and they can be reused. The reactivity of the catalyst can be tuned by changing

  固体载体上的不对称有机催化结合了无金属催化剂的环境优势和固体载体试剂的易操作性。对映选择性的有机催化DielsAlder反应已通过两种不同的固体负载手性有机催化剂得到证明。催化剂易于回收，可以重复使用。可以通过改变固体载体来调节催化剂的反应性。
• Ionic liquids and their use
  申请人：——

  公开号：US20040054231A1

  公开（公告）日：2004-03-18

  Ionic compounds having a freezing point of no more than 50° C., formed by the reaction of at least one amine salt of the formula R 1 R 2 R 3 R 4 N + X − (I) with at least one hydrated salt, which is a chloride, nitrate, sulphate or acetate of Li, Mg, Ca, Cr, Mn, Fe, Co, Ni, Cu, Zn, Cd, Pb, Bi, La or Ce; wherein R 1 , R 2 and R 3 are each independently a C 1 to C 5 alkyl or a C 6 to C 10 cycloalkyl group, or wherein R 2 and R 3 taken together represent a C 4 to C 10 alkylene group, thereby forming with the N atom of formula (I) a 5 to 11 membered heterocyclic ring, and wherein R 4 is hydrogen, or phenyl, or C 1 to C 12 alkyl or cycloalkyl group, optionally substituted with at least one group selected from OH, Cl, Br, F, I, phenyl, NH 2 , CN, NO 2 , COOR 5 , CHO, COR 5 and OR 5 , wherein R 5 is a C 1 to C 10 alkyl or cycloalkyl group, and X − is an anion capable of being complexed by the said hydrated salt. The compounds are useful as solvents, electrolytes, and catalysts, and have particular application in solvents/electrolytes for metal plating and electropolishing processes, in particular in chromium plating.

  具有冰点不超过50°C的离子化合物，由至少一种胺盐（化学式为R1R2R3R4N+X−（I））与至少一种水合盐反应形成，所述水合盐是Li、Mg、Ca、Cr、Mn、Fe、Co、Ni、Cu、Zn、Cd、Pb、Bi、La或Ce的氯化物、硝酸盐、硫酸盐或醋酸盐；其中R1、R2和R3分别独立地是C1到C5烷基或C6到C10环烷基，或者R2和R3一起代表C4到C10烷基烯基，从而与化学式（I）中的N原子形成5到11个成员的杂环环，其中R4是氢、苯基、C1到C12烷基或环烷基，可选择地取代至少一个来自OH、Cl、Br、F、I、苯基、NH2、CN、NO2、COOR5、CHO、COR5和OR5的基团，其中R5是C1到C10烷基或环烷基，X−是能够被所述水合盐络合的阴离子。这些化合物可用作溶剂、电解质和催化剂，在金属镀覆和电化学抛光过程中具有特殊应用，特别是在铬镀中。