octamethylene maleate | 145389-60-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: octamethylene maleate
• 英文别名: Octamethylene maleate；(3Z)-1,6-dioxacyclotetradec-3-ene-2,5-dione
• CAS: 145389-60-2
• 化学式: C₁₂H₁₈O₄
• 分子量: 226.273
• InChiKey: SXUWEONUUBUCSD-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  octamethylene maleate 、 1-diazo-2-(1-methyl-2-oxocyclohexyl)ethan-2-one 在 dirhodium tetraacetate 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以74%的产率得到
  参考文献：
  名称：

  α-重氮酮与大环烯烃的串联反应：氧杂硼硼烷稠合的大环内酯的非对映选择性合成

  摘要：

  在乙酸铑（II）催化剂的存在下，α-重氮酮与大环烯烃的串联环化-环加成反应可中等收率产生氧杂硼烷烷稠合的大环二或四内酯环体系。这形成了以大环烯烃作为双极性亲和剂进行的1,3-偶极环加成反应的第一个实例，从而提供了具有非对映选择性的各种新的氧杂降冰片烷稠合大环。

  DOI：

  10.1016/j.tet.2007.02.029
• 作为产物：
  描述：

  1,8-辛二醇 在 [Ru(2,6-Cl2tpp)CO] 对甲苯磺酰叠氮 、 sodium acetate 、 三乙胺 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 33.0h， 生成 octamethylene maleate
  参考文献：
  名称：

  Highly Selective Intra- and Intermolecular Coupling Reactions of Diazo Compounds to Form cis-Alkenes Using a Ruthenium Porphyrin Catalyst

  摘要：

  [Ru(2,6-Cl2TPP)(CO)] catalyzed intramolecular coupling reactions of bisdiazoacetates and intermolecular coupling reactions of monodiazoacetates to afford the coupling products in up to 76% and 93% yields, respectively. Only the cis isomers were obtained from the reactions. Employing such a ruthenium-catalyzed coupling reaction of a diazo compound as a key step allowed the synthesis of Patulolide B in 67% yield with a ratio of >40:1 against its trans isomer.

  DOI：

  10.1021/ol049626a

文献信息

• Gold-catalyzed intramolecular diazo coupling: an efficient macrocyclization towards cyclic olefins
  作者：Chenghao Zhu、Guangyang Xu、Kai Liu、Lin Qiu、Shiyong Peng、Jiangtao Sun

  DOI：10.1039/c5cc04830c

  日期：——

  A gold-catalyzed synthesis of medium to large membered cyclic olefins has been developed.

  一种利用金催化的合成中等到大环烯烃的方法已经开发出来了。
• Assembly of ion channel mimics from a modular construction set
  作者：Thomas M. Fyles、Tony D. James、Allana Pryhitka、Mohammad Zojaji

  DOI：10.1021/jo00078a026

  日期：1993.12

  Ion channel mimics were assembled from a modular construction set consisting of core units, derived from polycarboxylate 18-crown-6 ethers, wall units, derived from macrocyclic tetraesters, and polar head groups which provide overall amphiphilic character. The preparation of symmetrical and side-discriminated macrocyclic tetraesters from diols and maleic anhydride gave the required macrocycles in low yields by acid-catalyzed esterification, or by carboxylate alkylation. Addition of 1 equiv of 3-mercaptopropanol to the macrocyclic dienes gave the wall unit precursor. Coupling of the walls to the crown ether via esters was achieved by carboxylate alkylation. The syntheses were completed by Michael addition of head group thiolates. Twenty-one candidate ion channels of molecular weight 1600-4800 g/mol were prepared and characterized.
• [EN] VERSATILE BLODEGRADABLE ELASTIC POLYMERS FEATURED WITH DUAL CROSSLINKING MECHANISM FOR BIOMEDICAL APPLICATIONS<br/>[FR] POLYMÈRES ÉLASTIQUES BIODÉGRADABLES POLYVALENTS POURVUS D'UN MÉCANISME DE DOUBLE RÉTICULATION POUR DES APPLICATIONS BIOMÉDICALES
  申请人：UNIV TEXAS

  公开号：WO2009137715A2

  公开（公告）日：2009-11-12

  The present invention provides a dual crosslinked biodegradable polymer and methods of making and using the polymer. The dual crosslinked biodegradable polymer composition includes a multifunctional monomer; a diol; and an unsaturated di-acid at least partially polymerized to form a network and photocrosslinked into a dual crosslinked polymer network.
• Highly Selective Intra- and Intermolecular Coupling Reactions of Diazo Compounds to Form <i>cis</i>-Alkenes Using a Ruthenium Porphyrin Catalyst
  作者：Gong-Yong Li、Chi-Ming Che

  DOI：10.1021/ol049626a

  日期：2004.5.1

  [Ru(2,6-Cl2TPP)(CO)] catalyzed intramolecular coupling reactions of bisdiazoacetates and intermolecular coupling reactions of monodiazoacetates to afford the coupling products in up to 76% and 93% yields, respectively. Only the cis isomers were obtained from the reactions. Employing such a ruthenium-catalyzed coupling reaction of a diazo compound as a key step allowed the synthesis of Patulolide B in 67% yield with a ratio of >40:1 against its trans isomer.
• Tandem reactions of α-diazo ketones with macrocyclic olefins: diastereoselective synthesis of oxanorbornane fused macrocyclic lactones
  作者：Sengodagounder Muthusamy、Boopathy Gnanaprakasam

  DOI：10.1016/j.tet.2007.02.029

  日期：2007.4

  Tandem cyclization–cycloaddition reactions of α-diazo ketones with macrocyclic olefins in the presence of rhodium(II) acetate catalyst led to the oxanorbornane fused macrocyclic di- or tetralactone ring systems in moderate yield. This forms the first example of 1,3-dipolar cycloaddition reactions with a macrocyclic olefin as a dipolarophile, affording a variety of new oxanorbornane fused macrocycles

  在乙酸铑（II）催化剂的存在下，α-重氮酮与大环烯烃的串联环化-环加成反应可中等收率产生氧杂硼烷烷稠合的大环二或四内酯环体系。这形成了以大环烯烃作为双极性亲和剂进行的1,3-偶极环加成反应的第一个实例，从而提供了具有非对映选择性的各种新的氧杂降冰片烷稠合大环。