bicyclo<2.2.1>hept-5-ene-exo-2,exo-3-dimethanol diacetate | 142507-56-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: bicyclo<2.2.1>hept-5-ene-exo-2,exo-3-dimethanol diacetate
• 英文别名: 2-exo,3-exo-diacetoxymethyl-bicyclo[2.2.1]hept-5-ene；5-norbornene-2-exo-3-exo-2,3-dimethanol-2,3-diacetate；((1R,2R,3S,4S)-bicyclo[2.2.1]hept-5-ene-2,3-diyl)bis(methylene) diacetate；2-exo,3-exo-bis(acetoxymethyl)-bicyclo[2.2.1]hept-5-ene；(+/-)-exo-exo-2,3-diacetoxymethyl-bicyclo[2.2.1]hept-5-ene；[(1S,2S,3R,4R)-3-(acetyloxymethyl)-2-bicyclo[2.2.1]hept-5-enyl]methyl acetate
• CAS: 142507-56-0
• 化学式: C₁₃H₁₈O₄
• 分子量: 238.284
• InChiKey: VQMMDYWRKKLDAF-FNFFVJSTSA-N

物化性质

• 沸点：
  299.4±13.0 °C(Predicted)
• 密度：
  1.115±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  bicyclo<2.2.1>hept-5-ene-exo-2,exo-3-dimethanol diacetate 在 肼-D4 、 氧气 、 5-ethyl-3-methyllumiflavinium perchlorate 作用下， 以 乙腈 为溶剂， 25.0 ℃ 、101.32 kPa 条件下， 反应 8.0h， 以93%的产率得到2-exo,3-exo-diacetoxymethyl-bicyclo[2.2.1]heptane
  参考文献：
  名称：

  Flavin-Catalyzed Generation of Diimide:  An Environmentally Friendly Method for the Aerobic Hydrogenation of Olefins

  摘要：

  The first green and practical method for "aerobic hydrogenation" involving the use of hydrazine and an organocatalyst is described. Olefins can be hydrogenated by treatment with hydrazine in the presence of a 5-ethyl-3-methyllumiflavinium perchlorate (FlEt+.ClO4-) catalyst under O2 atmosphere to give the corresponding hydrogenated products in excellent yields along with environmentally benign water and molecular nitrogen as the only waste products.

  DOI：

  10.1021/ja053976q
• 作为产物：
  描述：

  5-norbornene-2,3-dimethanol 在 乙酸酐 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 bicyclo<2.2.1>hept-5-ene-exo-2,exo-3-dimethanol diacetate
  参考文献：
  名称：

  Five-membered carbocyclic and heterocyclic inhibitors of neuraminidases

  摘要：

  本文披露了一种化合物，其化学式为：这些化合物对抑制疾病致病微生物的神经氨酸酶具有用处，尤其是流感神经氨酸酶。还披露了用于预防和治疗由具有神经氨酸酶的微生物引起的疾病的组合物和方法，以及用于制备这些化合物的过程和用于这些过程中的合成中间体。

  公开号：

  US06518305B1

文献信息

• Aerobic Reduction of Olefins by In Situ Generation of Diimide with Synthetic Flavin Catalysts
  作者：Yasushi Imada、Hiroki Iida、Takahiro Kitagawa、Takeshi Naota

  DOI：10.1002/chem.201003278

  日期：2011.5.16

  5‐bis(acylamino)pyridine 15 exhibit unprecedented catalytic activities, with the reduction of aromatic and hydroxy olefins proceeding significantly faster when a higher‐generation dendrimer is used as a host pair for the association catalysts. Contrasting retardation is observed upon similar treatment of non‐aromatic or non‐hydroxy olefins with the dendrimer catalysts. Control experiments and kinetic studies

  通过用中性和阳离子合成黄素催化剂1和2对肼进行好氧氧化，可以有效地生成通用的还原剂二酰亚胺。该技术为有氧还原烯烃提供了一种方便，安全的方法，该方法是在O 2或空气中以1当量的肼进行的。高肼效率，简便安全的处理方法和独特的化学选择性已证明了其与传统的基于气体的方法相比具有综合优势。维生素B 2衍生物6由于具有很高的利用率和可回收性，因此可作为一种高度实用，坚固的催化剂。1 b的缔合体具有树枝状2,5-双（酰基氨基）吡啶15的化合物表现出空前的催化活性，当将更高级的树枝状大分子用作缔合催化剂的主体对时，芳烃和羟基烯烃的还原速度显着加快。在用树枝状聚合物催化剂对非芳族或非羟基烯烃进行类似处理时，观察到相反的阻滞作用。对照实验和动力学研究表明，这些催化反应包括由肼生成二酰亚胺的两个独立的厌氧和好氧过程。树枝状大分子对催化反应的正面和负面影响归因于肼和烯烃底物在缔合络合物催化剂的类酶反应腔中的特定包含。
• Neutral Flavins: Green and Robust Organocatalysts for Aerobic Hydrogenation of Olefins
  作者：Yasushi Imada、Takahiro Kitagawa、Takashi Ohno、Hiroki Iida、Takeshi Naota

  DOI：10.1021/ol902393p

  日期：2010.1.1

  Various olefins can be hydrogenated quantitatively with neutral flavin 2 catalysts in the presence of 1-2 equiv of hydrazine under 1 atm of O(2), Vitamin B(2) derivative 2g acts as a highly efficient and robust catalyst for the present environmentally benign process producing water and nitrogen gas as the only waste products.
• Facially Amphipathic Glycopolymers Inhibit Ice Recrystallization
  作者：Ben Graham、Alice E. R. Fayter、Judith E. Houston、Rachel C. Evans、Matthew I. Gibson

  DOI：10.1021/jacs.8b02066

  日期：2018.5.2

  Antifreeze glycoproteins (AFGPs) from polar fish are the most potent ice recrystallization (growth) inhibitors known, and synthetic mimics are required for low-temperature applications such as cell cryopreservation. Here we introduce facially amphipathic glycopolymers that mimic the three-dimensional structure of AFGPs. Glycopolymers featuring segregated hydrophilic and hydrophobic faces were prepared by ring-opening metathesis polymerization, and their rigid conformation was confirmed by small-angle neutron scattering. Ice recrystallization inhibition (IRI) activity was reduced when a hydrophilic oxo-ether was installed on the glycan-opposing face, but significant activity was restored by incorporating a hydrophobic dimethylfulvene residue. This biomimetic strategy demonstrates that segregated domains of distinct hydrophilicity/hydrophobicity are a crucial motif to introduce IRI activity, which increases our understanding of the complex ice crystal inhibition processes.
• Bi(OTf)3—a mild catalyst for the synthesis of difficult to obtain C-alkyl substituted glycolurils
  作者：Feng Wu、Vijaybabu Mandadapu、Anthony I. Day

  DOI：10.1016/j.tet.2013.09.071

  日期：2013.11

  We have employed Bi(OTf)(3) (5 mol %) a catalyst not previously used in the synthesis of urea condensation products from alpha-dicarbonyl compounds, as a mild method for the synthesis of difficult to obtain glycolurils. There are limited synthetic examples of C-alkylated substituted glycolurils and even fewer carrying functionality on the alkyl substituent. We have successfully synthesised some challenging examples of glycolurils with functionality, which include norbornyl-based structures. The milder reaction conditions enables the isolation of defined intermediate diols and ureas in good yields, and glycolurils are possible, where they would not normally be available under conventional acid catalyzed conditions. (C) 2013 Published by Elsevier Ltd.
• Ambivalent Role of Rotamers in Cyclic(alkyl)(amino)carbene Ruthenium Complexes for Enantioselective Ring-Opening Cross-Metathesis
  作者：Jennifer Morvan、François Vermersch、Ziyun Zhang、Thomas Vives、Thierry Roisnel、Christophe Crévisy、Laura Falivene、Luigi Cavallo、Nicolas Vanthuyne、Guy Bertrand、Rodolphe Jazzar、Marc Mauduit

  DOI：10.1021/acs.organomet.3c00054

  日期：2023.3.27