(±)-anastrephin | 86003-24-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (±)-anastrephin
• 英文别名: (+/-)-anastrephin；anastrephin；(3aR,4S,7aR)-4-ethenyl-4,7a-dimethyl-3a,5,6,7-tetrahydro-3H-1-benzofuran-2-one
• CAS: 86003-24-9
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: VWOPTUCATATVGQ-YUSALJHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (±)-anastrephin 在 2-羟基吡啶 、 sodium hydroxide 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 48.0h， 生成 (1R,2R,6S)-(-)-(2-Hydroxy-2,6-dimethyl-6-vinylcyclohexyl)acetic acid
  参考文献：
  名称：

  Resolution and assignment of absolute configuration to the enantiomers of anastrephin and epianastrephin and their analogs

  摘要：

  DOI：

  10.1021/jo00375a016
• 作为产物：
  描述：

  (E,E)-9-Chloro-3,7-dimethyl-1-(tetrahydropyran-2'-yloxy)-2,7-nonadiene 在 氢氧化钾 、 正丁基锂 、 溶剂黄146 、 三苯基膦 、 mercury dichloride 、 mercury(II) oxide 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 反应 26.5h， 生成 (±)-anastrephin
  参考文献：
  名称：

  Stereospecific Synthesis of Suspensolide, a Male-Produced Pheromone of the Caribbean Fruit Fly, Anastrepha suspensa (Loew), and the Mexican Fruit Fly, Anastrepha ludens (Loew)

  摘要：

  An efficient synthesis of (E,E)-4,8-dimethyl-3,8-decadien-10-olide, suspensolide, a major component of the pheromone blend of the Caribbean and Mexican fruit flies, is described. The synthesis involves dicarboalumination of 1,6-heptadiyne with in situ conversion to a dialanate and reaction with paraformaldehyde. Monoprotection of the symmetrical diol formed in this process as the mono-THP derivative allowed conversion of the free hydroxyl to the chloride (NCS/DMS). Addition of one carbon to the chain was achieved by displacement of the chloride by cyanide (phase-transfer conditions) or the lithium salt of a thioorthoester. Hydrolysis of the masked carbonyls and deprotection of the omega-hydroxyl gave (E,E)-4,8-dimethyl-10-hydroxy-3,8-decadienoic acid. This diunsaturated hydroxy acid was cyclized to suspensolide in 30% yield using Mitsunobu conditions. The overall yield of suspensolide in this eight-step synthesis was 10%.

  DOI：

  10.1021/jo00096a029

文献信息

• Diastereoselective Synthesis of (±)-Epianastrephin, (±)-Anastrephin and Analogs Thereof
  申请人：The United States of America, as Represented by the Secretary of Agriculture

  公开号：US20170305874A1

  公开（公告）日：2017-10-26

  A process for the synthesis of trans-fused γ-lactones having Formula (IV) from substituted cyclic ketones having Formula (I). A diastereoselective synthesis of (±)-epianastrephin (1) (wherein: R 1 is ethenyl, R 2 and R 3 is methyl, and n is 1), (±)-anastrephin (2) (wherein: R 2 is ethenyl, R 1 and R 3 is methyl and n is 1), and analogs thereof (wherein: R 1 is H, C 1-5 alkyl, C 2-6 alkenyl or C 2-6 alkynyl, R 2 is H, C 1-5 alkyl, C 2-6 alkenyl or C 2-6 alkynyl, R 1 and R 2 together with the carbon atom they are attached form a C 3-6 cycloalkyl ring, R 3 is C 1-5 alkyl and n is 0-2):

  从具有化学式（I）的取代环状酮合成具有化学式（IV）的反式γ-内酯的过程。对（±）-epianastrephin（1）进行立体选择合成（其中：R1为乙烯基，R2和R3为甲基，n为1），（±）-anastrephin（2）进行立体选择合成（其中：R2为乙烯基，R1和R3为甲基，n为1），以及它们的类似物（其中：R1为H，C1-5烷基，C2-6烯基或C2-6炔基，R2为H，C1-5烷基，C2-6烯基或C2-6炔基，R1和R2与它们附着的碳原子一起形成C3-6环烷基环，R3为C1-5烷基，n为0-2）。
• SYNTHESIS OF (±)-ANASTREPHIN AND (±)-EPIANASTREPHIN
  作者：Akira Saito、Hajime Matsushita、Hajime Kaneko

  DOI：10.1246/cl.1984.729

  日期：1984.5.5

  (±)-Anastrephin and (±)-epianastrephin, sex and aggregation pheromenes of Caribbean and Mexican fruit flies, were synthesized by acid-catalyzed cyclization of 10-hydroxy-4,8-dimethyldeca-(3E,8E)-3,8-dienoic acid in 67% yield as a 1:1 mixture.

  通过酸催化环化 10-羟基-4,8-二甲基癸-(3E,8E)-3,8-二烯酸合成了加勒比和墨西哥果蝇的 (±)-Anastrephin 和 (±)-epianastrephin 性信息素和聚集信息素，它们是 1:1 的混合物，收率为 67%。
• Anastrephin and epianastrephin, novel lactone components isolated from the sex pheromone blend of male caribbean and mexican fruit flies
  作者：Merle A Battiste、Lucjan Strekowski、David P Vanderbilt、Melean Visnick、Roy W King、James L Nation

  DOI：10.1016/s0040-4039(00)87958-7

  日期：1983.1

  Anastrephin and epianastrephin, novel lactone components isolated from the male produced pheromone of two Anastrepha fruit fly species (Caribbean and Mexican) are assigned the structure and relative stereochemistry and , respectively, on the basis of spectroscopic and chemical evidence including synthesis.

  Anastrephin和从两个阳生产信息素分离epianastrephin，新颖内酯组分按实蝇果蝇物种（加勒比和墨西哥）被分配的结构和相对立体化学和分别的光谱和化学证据包括合成的基础上。
• Resolution and assignment of absolute configuration to the enantiomers of anastrephin and epianastrephin and their analogs
  作者：Lucjan Strekowski、Melean Visnick、Merle A. Battiste

  DOI：10.1021/jo00375a016

  日期：1986.12
• MORI, KEHNDZI;NAKADZONO, YUTAKA
  作者：MORI, KEHNDZI、NAKADZONO, YUTAKA

  DOI：——

  日期：——