6,7-二氯-3-氧杂二环[3.2.0]庚烷-2,4-二酮 | 89361-81-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 中文名称: 6,7-二氯-3-氧杂二环[3.2.0]庚烷-2,4-二酮
• 英文名称: 6,7-dichloro-3-oxabicyclo[3.2.0]heptane-2,4-dione
• 英文别名: 3,4-dichloro-cyclobutane-1,2-dicarboxylic acid anhydride；3,4-Dichlor-cyclobutan-dicarbonsaeure-(1,2)-anhydrid
• CAS: 89361-81-9
• 化学式: C₆H₄Cl₂O₃
• 分子量: 195.002
• InChiKey: SVWYPMPUZSZFRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6,7-二氯-3-氧杂二环[3.2.0]庚烷-2,4-二酮 在 lithium aluminium tetrahydride 、 乙酸酐 、 锌 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 cis-3-cyclobutene-1,2-dimethanol
  参考文献：
  名称：

  2-氮杂双环[2.1.1]己烷的新合成。

  摘要：

  从顺式-环丁-3-烯-1,2-二羧酸酐7开始，已经完成了2-氮杂双环[2.1.1]己烷环系统的有效合成，该顺式-环丁-3-烯-1,2-二羧酸酐是使用光化学方法制备的。该新策略的关键步骤涉及将苯硒基溴化物立体选择性地亲电子加成至衍生自7的环丁二氨基甲酸酯16的双键。随后在氢化钠存在下17a的闭环反应使2-氮杂双环己烷化合物18具有令人满意的总体让。还原性除去苯基硒烯基并随后脱保护，迅速导致在碳环上官能化的氨基衍生物4a。然后从中间体二磺酰胺23合成羟基和羧酸衍生物4b，c。在另外三个步骤之后，用乙酸钾置换活化的氨基，得到羟基衍生物4b。最后，在琼斯条件下氧化4b的醇官能团，然后进行氢解，得到羧酸衍生物4c，它是2,4-methanoproline 1的第一个报道的β-异构体。

  DOI：

  10.1021/jo001790y
• 作为产物：
  描述：

  马来酸酐 、 反-1,2-二氯乙烯 以 乙酸乙酯 为溶剂， 生成 6,7-二氯-3-氧杂二环[3.2.0]庚烷-2,4-二酮
  参考文献：
  名称：

  2-氮杂双环[2.1.1]己烷的新合成。

  摘要：

  从顺式-环丁-3-烯-1,2-二羧酸酐7开始，已经完成了2-氮杂双环[2.1.1]己烷环系统的有效合成，该顺式-环丁-3-烯-1,2-二羧酸酐是使用光化学方法制备的。该新策略的关键步骤涉及将苯硒基溴化物立体选择性地亲电子加成至衍生自7的环丁二氨基甲酸酯16的双键。随后在氢化钠存在下17a的闭环反应使2-氮杂双环己烷化合物18具有令人满意的总体让。还原性除去苯基硒烯基并随后脱保护，迅速导致在碳环上官能化的氨基衍生物4a。然后从中间体二磺酰胺23合成羟基和羧酸衍生物4b，c。在另外三个步骤之后，用乙酸钾置换活化的氨基，得到羟基衍生物4b。最后，在琼斯条件下氧化4b的醇官能团，然后进行氢解，得到羧酸衍生物4c，它是2,4-methanoproline 1的第一个报道的β-异构体。

  DOI：

  10.1021/jo001790y

文献信息

• Designing hybrid foldamers: the effect on the peptide conformational bias of β- versus α- and γ-linear residues in alternation with (1R,2S)-2-aminocyclobutane-1-carboxylic acid
  作者：Sergio Celis、Esther Gorrea、Pau Nolis、Ona Illa、Rosa M. Ortuño

  DOI：10.1039/c1ob06575k

  日期：——

  Several oligomers constructed with (1R,2S)-2-aminocyclobutane-1-carboxylic acid and glycine, β-alanine, and γ-amino butyric acid (GABA), respectively, joined in alternation have been synthesized and studied by means of NMR and CD experiments as well as with computational calculations. Results account for the spacer length effect on folding and show that conformational preference for these hybrid peptides can be tuned from β-sheet-like folding for those containing a C2 or C4 linear segment to a helical folding for those with a C3 spacer between cyclobutane residues. The introduction of cyclic spacers between these residues does not modify the extended ribbon-type structure previously manifested in poly(cis-cyclobutane) β-oligomers.

  用(1R,2S)-2-氨基环丁烷-1-羧酸、甘氨酸、β-丙氨酸和γ-氨基丁酸分别交替连接而成的几种寡聚体，已通过NMR和CD实验以及计算模拟进行了合成和研究。结果解释了间隔长度对折叠的影响，并表明这些杂合肽的构象偏好可以从含有C2或C4线性段的对β片层样折叠调节为含有C3间隔的环丁烷残基之间的螺旋折叠。在这些残基之间引入环形间隔不会改变之前在多(顺式-环丁烷)β-寡聚体中展现的扩展带状结构。
• Folding and self-assembling with β-oligomers based on (1R,2S)-2-aminocyclobutane-1-carboxylic acid
  作者：Elisabeth Torres、Esther Gorrea、Kepa K. Burusco、Eric Da Silva、Pau Nolis、Federico Rúa、Stéphanie Boussert、Ismael Díez-Pérez、Samantha Dannenberg、Sandra Izquierdo、Ernest Giralt、Carlos Jaime、Vicenç Branchadell、Rosa M. Ortuño

  DOI：10.1039/b918755c

  日期：——

  Improved methodologies are provided to synthesize (1R,2S)-2-aminocyclobutane-1-carboxylic acid derivatives and their incorporation into β-peptides of 2–8 residues bearing different N-protecting groups. The conformational analysis of these oligomers has been carried out by using experimental techniques along with theoretical calculations. This study shows that these oligomers adopt preferentially a strand-type conformation in solution induced by the formation of intra-residue six-membered hydrogen-bonded rings, affording cis-fused [4.2.0]octane structural units that confer high rigidity on these β-peptides. Moreover, all of them are prone to self-assemble producing nano-sized fibres, as evidenced by TEM, AFM and SPFM, and, in some instances, they also form gels. These techniques and molecular modelling allowed us to suggest an aggregation model for the assembly structures in which a parallel molecular-arrangement is preferred and the conformation is similar to that observed in solution. According to this model, both hydrogen-bonding and hydrophobic interactions would account for formation of the assemblies.

  本研究提供了改进的方法来合成(1R,2S)-2-氨基环丁烷-1-羧酸衍生物，并将其加入带有不同 N 保护基团的 2â8 个残基的 δ 肽中。通过实验技术和理论计算，对这些低聚物进行了构象分析。研究结果表明，这些低聚物在溶液中优先采用的是由残基内六元氢键环的形成所诱导的链型构象，形成顺式融合的[4.2.0]辛烷结构单元，赋予这些δ肽高刚性。此外，正如 TEM、AFM 和 SPFM 所证明的那样，所有这些δ肽都容易自组装生成纳米级纤维，在某些情况下，它们还能形成凝胶。通过这些技术和分子建模，我们提出了一种组装结构的聚集模型，在该模型中，平行分子排列是首选，其构象与溶液中观察到的构象相似。根据该模型，氢键和疏水相互作用都是形成组装体的原因。
• POLYAMIC ACID AND POLYIMIDE
  申请人：Suzuki Hideo

  公开号：US20090292103A1

  公开（公告）日：2009-11-26

  A polyamic acid comprising at least 10 mol % repeating units represented by the formula [1] or [2]; and a polyimide represented by the formula [3] or [4] which is obtained from the polyamic acid. A polyimide film having high heat resistance and satisfactory in light-transmitting properties and tensile strength is obtained from the polyamic acid. (In the formulae, R 1 and R 2 each independently represents hydrogen or C 1-10 alkyl; R 3 and R 4 each independently represents hydrogen, halogeno, C 1-10 alkyl, or phenyl or the R 3 and R 4 on adjoining carbon atoms are bonded to each other to form C 3-8 cycloalkyl or phenyl; R 5 represents a divalent organic group; and n is an integer of 2 or larger.)
• GLYCOSYLATED LINKER, COMPOUND CONTAINING GLYCOSYLATED LINKER MOIETY AND PHYSIOLOGICALLY ACTIVE SUBSTANCE MOIETY OR SALT THEREOF, AND METHODS FOR PRODUCING SAID U OR SALT THEREOF
  申请人：GLYTECH, INC.

  公开号：US20150299337A1

  公开（公告）日：2015-10-22

  [Problem] The purpose is to provide a compound containing a carrier linker moiety and a physiologically active substance moiety or a salt of the compound, wherein a carrier in the carrier linker moiety is biodegradable and is soluble in water. [Solution] The purpose can be achieved by employing a sugar chain as a carrier and focusing on the structure of a carrier-linker having a specified structure. A compound containing a carrier linker moiety and a physiologically active substance moiety or a salt of the compound is discovered.
• US8067527B2
  申请人：——

  公开号：US8067527B2

  公开（公告）日：2011-11-29