乙基(15R)-15-氰基四环[6.6.2.02,7.09,14]十六-2,4,6,9,11,13-己烯-15-羧酸酯 | 19277-46-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 乙基(15R)-15-氰基四环[6.6.2.02,7.09,14]十六-2,4,6,9,11,13-己烯-15-羧酸酯
• 英文名称: ethyl 9,10-dihydro-9,10-endoethanoanthracene-11-cyano-11-carboxylate
• 英文别名: ethyl 11-cyano-9,10-dihydro-9,10-ethanoanthracene-11-carboxylate；ethyl cyanoacrylate-anthracene adduct；ethyl 11-cyano-9,10-dihydroendo-9,10-ethanoanthracene-11-carboxylate；11-cyano-11-(ethoxycarbonyl)-9,10-dihydro-9,10-endo-ethanoanthracene；Ethyl 15-cyanotetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaene-15-carboxylate
• CAS: 19277-46-4
• 化学式: C₂₀H₁₇NO₂
• 分子量: 303.36
• InChiKey: HTMUDVNXDOBHRU-UHFFFAOYSA-N

物化性质

• 熔点：
  118 °C
• 沸点：
  466.3±45.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙基(15R)-15-氰基四环[6.6.2.02,7.09,14]十六-2,4,6,9,11,13-己烯-15-羧酸酯 在 4-二甲氨基吡啶 、 四磷十氧化物 、 对苯二酚 、 N,N'-二环己基碳二亚胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 5,5-dimethyl-1,3-cyclohexadiene 、 二氯甲烷 、 水 为溶剂， 反应 64.0h， 生成 dibenzobarallene
  参考文献：
  名称：

  Fluorescent Cyanoacrylate Monomers and Polymers for Fingermark Development

  摘要：

  Cyanoacrylate esters with fluorescent side groups were synthesized and tested as agents for latent fingerprint development. Reactive monomers with benzyl, anthracyl, naphthyl, fluorenyl, propagyl, and cyanomethyl side groups were synthesized using the formation of an ethyl cyanoacrylate, anthracene adduct, followed by hydrolysis of the ethyl ester to the acid and esterification with a desired alcohol, and finally release of the monomer by retro-Diels-Alder with maleic anhydride. Monomers were prepared in high yield and purity as determined by spectral analysis. Attempts to synthesize these monomers from poly(ethyl cyanoacrylate) by transesterification and depolymerization resulted in low yields and low purity. The synthesized fluorescent monomers were found to be effective for latent fingerprint development in solution forming clear fluorescent fingerprint images suitable for forensic fingerprint comparison. These monomers can complement the current use of the commonly used nonfluorescent ethyl cyanoacrylate monomers for fingerprint development.

  DOI：

  10.1021/ma400837h
• 作为产物：
  描述：

  氰基丙烯酸乙酯 、 蒽 以 甲苯 为溶剂， 反应 48.0h， 生成 乙基(15R)-15-氰基四环[6.6.2.02,7.09,14]十六-2,4,6,9,11,13-己烯-15-羧酸酯
  参考文献：
  名称：

  A cross-linking strategy provides a new generation of biodegradable and biocompatible cyanoacrylate medical adhesives

  摘要：

  一项通用策略提供了一种新一代可生物降解和生物相容的氰基丙烯酸医用胶粘剂。

  DOI：

  10.1039/c6tb00235h

文献信息

• Development of New HPLC Chiral Stationary Phases Based on Native and Derivatized Cyclofructans
  作者：Ping Sun、Chunlei Wang、Zachary S. Breitbach、Ying Zhang、Daniel W. Armstrong

  DOI：10.1021/ac902257a

  日期：2009.12.15

  An unusual class of chiral selectors, cyclofructans, is introduced for the first time as bonded chiral stationary phases. Compared to native cyclofructans (CFs), which have rather limited capabilities as chiral selectors, aliphatic- and aromatic-functionalized CF6s possess unique and very different enantiomeric selectivities. Indeed, they are shown to separate a very broad range of racemic compounds. In particular, aliphatic-derivatized CF6s with a low substitution degree baseline separate all tested chiral primary amines. It appears that partial derivatization on the CF6 molecule disrupts the molecular internal hydrogen bonding, thereby making the core of the molecule more accessible. In contrast, highly aromatic-functionalized CF6 stationary phases lose most of the enantioselective capabilities toward primary amines, however they gain broad selectivity for most other types of analytes. This class of stationary phases also demonstrates high “loadability” and therefore has great potential for preparative separations. The variations in enantiomeric selectivity often can be correlated with distinct structural features of the selector. The separations occur predominantly in the presence of organic solvents.

  首次引入一类不寻常的手性选择剂——环糊精作为键合型手性固定相。与天然环糊精（CFs）相比，其作为手性选择剂的能力相当有限，而脂族和芳族功能化的CF6具有独特且截然不同的对映体选择性。事实上，它们能够分离非常广泛的消旋化合物。特别是，低取代度的脂族衍生化CF6能够基线分离所有测试的手性伯胺。似乎部分衍生化作用于CF6分子会破坏分子内部的氢键，从而使分子核心更易接近。相比之下，高度芳族功能化的CF6固定相在伯胺的对映选择能力方面丧失了大部分能力，但它们对大多数其他类型的分析物获得了广泛的选择性。这类固定相还表现出高“负荷能力”，因此具有在制备分离方面的巨大潜力。对映体选择性的变化通常可以与选择剂的独特结构特征相关联。分离主要在有机溶剂存在下发生。
• ALTERNATIVE SYNTHESIS OF 1,1-SUBSTITUTED OLEFINS HAVING ELECTRON-WITHDRAWING SUBSTITUENTS
  申请人：Friese Carsten

  公开号：US20120289734A1

  公开（公告）日：2012-11-15

  A three-stage method for synthesizing 1,1-disubstituted olefins is provided.

  提供了一种合成1,1-二取代烯烃的三阶段方法。
• [EN] COMPOSITIONS AND METHODS FOR CYCLOFRUCTANS AS SEPARATION AGENTS<br/>[FR] COMPOSITIONS ET PROCÉDÉS POUR DES CYCLOFRUCTANES EN TANT QU'AGENTS DE SÉPARATION
  申请人：UNIV TEXAS

  公开号：WO2010148191A3

  公开（公告）日：2011-05-19
• INJECTIBLE CYANOACRYLATE-FUNCTIONALIZED POLYISOBUTYLENES
  申请人：The University of Akron

  公开号：EP2155107B1

  公开（公告）日：2016-04-13
• BIODEGRADABLE MEDICAL ADHESIVE AND PREPARATION METHOD AND USE THEREOF
  申请人：INSTITUTE OF PHARMACOLOGY AND TOXICOLOGY ACADEMY OF MILITARY MEDICAL SCIENCES P.L.A.

  公开号：US20140369952A1

  公开（公告）日：2014-12-18

  A medical adhesive with good biodegradable performance capable of undergoing crosslinking copolymerization, comprising a mono-alpha-cyanoacrylate and a bis-alpha-cyanoacrylic acid diol ester monomer molecule. The olefinic bonds in the mono-alpha-cyanoacrylate structure are polymerized in the presence of infinitesimal anions to form a solid 3D high polymer; the 3D high polymer is provided with degradation sites on the web-like backbone chain, with clear degradation path and absorbable degradation products. The medical adhesive can be used for wound adhesive, large area wound hemostasia, and visceral and soft tissue wound closure.