(E)-7-nitrohept-6-enal | 1114553-80-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-7-nitrohept-6-enal
• CAS: 1114553-80-8
• 化学式: C₇H₁₁NO₃
• 分子量: 157.169
• InChiKey: QTTGDXPUHCGQDE-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-7-nitrohept-6-enal 在 盐酸 、 (2R)-2-[二苯基[(三甲基硅酯)氧基]甲基]-吡咯烷 、 水 、 溶剂黄146 、 苯甲酸 、 锌 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 35.5h， 生成 (1R,3aS,6aR)-octahydrocyclopenta[c]pyrrole-1-carboxylic acid
  参考文献：
  名称：

  解开对称的C 2-氮杂四氢醌系统。简单的对映选择性合成

  摘要：

  描述了到C 2对称的氮杂四喹烷1（或对映体）的立体控制合成路线。合成的成功实施涉及[3 + 2]环加成和立体化学控制方法的创新。

  DOI：

  10.1021/acs.orglett.1c00387
• 作为产物：
  描述：

  7,7-dimethoxyhept-1-ene 在 盐酸 、 silver(I) nitrite 、 2,2,6,6-四甲基哌啶氧化物 作用下， 以 溶剂黄146 、 1,2-二氯乙烷 为溶剂， 反应 37.0h， 生成 (E)-7-nitrohept-6-enal
  参考文献：
  名称：

  Organocatalytic Access to a cis-Cyclopentyl-γ-amino Acid: An Intriguing Model of Selectivity and Formation of a Stable 10/12-Helix from the Corresponding γ/α-Peptide

  摘要：

  In this study, we have developed a highly enantioselective organocatalytic route to the (1S,2R)-2-(aminomethyl)cyclopentane-1-carboxylic acid monomer precursor, which has a cis-configuration between the C- and N-termini around the cyclopentane core. Kinetic measurements show that the product distribution changes over time due to epimerization of the C1 center. Computations suggest the cis-selectivity is a result of selective C-C bond formation, while subsequent steps appear to influence the selectivity at higher temperature. The resulting gamma-amino acid residue was incorporated into a novel gamma/alpha-peptide, which forms a well-ordered 10/12-helix with alternate H-bond directionality in spite of the smallest value of the zeta-angle yet observed for a helix of this type. This highly defined structure is also a result of the narrow range of potential zeta-angles in our monomer. In contrast, the larger range of potential zeta-values observed for the corresponding trans-system can be fulfilled by several competing helical structures.

  DOI：

  10.1021/jacs.9b10861

文献信息

• Asymmetric Synthesis of Polyfunctionalized Mono-, Bi-, and Tricyclic Carbon Frameworksvia Organocatalytic Domino Reactions
  作者：Dieter Enders、Matthias R. M. Hüttl、Gerhard Raabe、Jan W. Bats

  DOI：10.1002/adsc.200700396

  日期：2008.1.25

  multi-component domino reaction is used as a key process for the stereoselective synthesis of polysubstituted mono- and bicyclic cyclohexene-carbaldehydes. Furthermore, the extension of the domino reaction and further synthetic transformations of the cascade products were investigated. The combination of the three-step cascade with an intramolecular Diels–Alder reaction opens up an entry to tricyclic decahydroacenaphthylene

  不对称的有机催化多组分多米诺反应被用作立体选择性合成多取代的单环和双环环己烯-甲醛的关键过程。此外，研究了多米诺骨牌反应的扩展和级联产物的进一步合成转化。三步级联反应与分子内Diels-Alder反应的结合为三环十氢化ac烯和十氢苯并菲骨架打开了大门，这是天然产物的重要特征碳核。
• TRIAZOLIUM CARBENE CATALYSTS AND PROCESSES FOR ASYMMETRIC CARBON-CARBON BOND FORMATION
  申请人：Rovis Tomislav

  公开号：US20130116445A1

  公开（公告）日：2013-05-09

  Provided herein are chiral triazolium catalysts useful for asymmetric C—C bond formation and processes for their preparation. Also provided are synthetic reactions in which these catalysts are used, in particular, in asymmetric C—C bond formation.

  本文提供了手性三唑铵催化剂，适用于不对称C-C键形成，并提供了其制备过程。同时提供了使用这些催化剂进行合成反应的方法，特别是在不对称C-C键形成中的应用。
• [EN] TRIAZOLIUM CARBENE CATALYSTS AND PROCESSES FOR ASYMMETRIC CARBON-CARBON BOND FORMATION<br/>[FR] CATALYSEURS À BASE DE CARBÈNE DE TRIAZOLIUM ET PROCÉDÉS POUR FORMER DES LIAISONS CARBONE-CARBONE ASYMÉTRIQUES
  申请人：UNIV COLORADO STATE RES FOUND

  公开号：WO2012009372A2

  公开（公告）日：2012-01-19

  Provided herein are chiral triazolium catalysts useful for asymmetric C-C bond formation and processes for their preparation. Also provided are synthetic reactions in which these catalysts are used, in particular, in asymmetric C-C bond formation.
• Organocatalytic Access to a <i>cis</i>-Cyclopentyl-γ-amino Acid: An Intriguing Model of Selectivity and Formation of a Stable 10/12-Helix from the Corresponding γ/α-Peptide
  作者：Rossana Fanelli、Dénes Berta、Tamás Földes、Edina Rosta、Robert Andrew Atkinson、Hans-Jörg Hofmann、Kenneth Shankland、Alexander J. A. Cobb

  DOI：10.1021/jacs.9b10861

  日期：2020.1.22

  In this study, we have developed a highly enantioselective organocatalytic route to the (1S,2R)-2-(aminomethyl)cyclopentane-1-carboxylic acid monomer precursor, which has a cis-configuration between the C- and N-termini around the cyclopentane core. Kinetic measurements show that the product distribution changes over time due to epimerization of the C1 center. Computations suggest the cis-selectivity is a result of selective C-C bond formation, while subsequent steps appear to influence the selectivity at higher temperature. The resulting gamma-amino acid residue was incorporated into a novel gamma/alpha-peptide, which forms a well-ordered 10/12-helix with alternate H-bond directionality in spite of the smallest value of the zeta-angle yet observed for a helix of this type. This highly defined structure is also a result of the narrow range of potential zeta-angles in our monomer. In contrast, the larger range of potential zeta-values observed for the corresponding trans-system can be fulfilled by several competing helical structures.
• Unraveling the C₂-Symmetric Azatetraquinane System. Simple, Enantioselective Syntheses
  作者：G. Sudhakar Reddy、D. Srinivas Reddy、E. J. Corey

  DOI：10.1021/acs.orglett.1c00387

  日期：2021.3.19

  Concise stereocontrolled synthetic routes to the C2-symmetric azatetraquinane 1 (or, also, the enantiomer) are described. The successful execution of the synthesis involved innovation in the methodology for [3+2] cycloaddition and stereochemical control.

  描述了到C 2对称的氮杂四喹烷1（或对映体）的立体控制合成路线。合成的成功实施涉及[3 + 2]环加成和立体化学控制方法的创新。