cis/trans-Hexahydro-1H-cycloheptafuran-1,3-dione | 4432-22-8

• 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: cis/trans-Hexahydro-1H-cycloheptafuran-1,3-dione
• 英文别名: cycloheptane1,2-dicarboxylic acid anhydride；4,5,6,7,8,8a-hexahydro-3aH-cyclohepta[c]furan-1,3-dione
• CAS: 4432-22-8
• 化学式: C₉H₁₂O₃
• 分子量: 168.192
• InChiKey: SDVIYPBSYKHGTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  cis/trans-Hexahydro-1H-cycloheptafuran-1,3-dione 在 sodium tetrahydroborate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.67h， 生成 trans-8a-(2-Hexynyl)octahydro-1H-cycloheptafuran-1-one
  参考文献：
  名称：

  Formation of trans ring-fused compounds by an alkylation-radical cyclization sequence

  摘要：

  Enolates derived from bicyclic lactones of type 1 (Scheme I) can be alkylated with 2-propynylic halides to give products 2, in which the unsaturated alkyl group is syn to the adjacent ring-fusion hydrogen. Reaction of 2 with sodium phenyl selenide and then with diazomethane produces esters 3, and these give trans ring-fused bicyclic compounds 4 when treated with triphenyltin hydride in the presence of a radical initiator. The bicyclic compounds afford ketones on double-bond cleavage, and the angular ester function can be converted into a methyl group. Similar processes occur if an aldehyde is used in the first step instead of a halide. The methodology is general.

  DOI：

  10.1021/jo00076a057

文献信息

• Influence of bicyclic anhydride structure on the outcome of the Castagnoli–Cushman reaction
  作者：Oleh K. Smyrnov、Mykhailo I. Adamovskyi、Tetiana V. Druzhenko、Kostiantyn P. Melnykov、Dmitriy M. Volochnyuk、Sergey V. Ryabukhin

  DOI：10.1007/s10593-023-03211-0

  日期：2023.7

  Castagnoli–Cushman reaction was carried out with various fused and bridged bicyclic anhydrides. The influence of the anhydride nature and, specifically, the size of fused anhydride rings on the reaction pathway were investigated. The negative outcome of the reaction in the case of small rings and bridged systems was mechanistically described. The scope and limitations of the procedure involving anhydrides and imines

  Castagnoli-Cushman 反应是用各种稠合和桥联的双环酸酐进行的。研究了酸酐性质，特别是稠合酸酐环的尺寸对反应途径的影响。机械地描述了小环和桥接系统中反应的负面结果。讨论了涉及酸酐和亚胺的程序的范围和局限性。证明了该方法具有较高的非对映选择性，并与前期结果具有相关性。该反应经过优化并扩大规模，可在单次运行中提供数克量的产物（最多 50 克）。
• GLYCOSYLATED LINKER, COMPOUND CONTAINING GLYCOSYLATED LINKER MOIETY AND PHYSIOLOGICALLY ACTIVE SUBSTANCE MOIETY OR SALT THEREOF, AND METHODS FOR PRODUCING SAID COMPOUND OR SALT THEREOF
  申请人：Glytech, Inc.

  公开号：EP2924053A1

  公开（公告）日：2015-09-30

  [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.

  [问题]目的是提供一种含有载体连接体分子和生理活性物质分子或化合物盐的化合物，其中载体连接体分子中的载体可生物降解并可溶于水。 [解]采用糖链作为载体，并注重具有特定结构的载体连接体的结构，可以达到上述目的。发现了一种含有载体连接体分子和生理活性物质分子或化合物盐的化合物。
• PROCESS FOR THE PREPARATION OF CHLORINE-RESISTANT POLYESTER SEMIPERMEABLE MEMBRANES
  申请人：AlliedSignal Inc.

  公开号：EP0467903B1

  公开（公告）日：1992-12-30
• IMPROVED MATRIX METALLOPROTEASE INHIBITORS
  申请人：GALARDY, Richard, E.

  公开号：EP0558648A1

  公开（公告）日：1993-09-08
• EP0558648A4
  申请人：——

  公开号：EP0558648A4

  公开（公告）日：1993-11-24