(-)-7a-Epianastrephin | 146451-40-3

• 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: (-)-7a-Epianastrephin
• 英文别名: (3aS,4R,7aR)-4-ethenyl-4,7a-dimethyl-3a,5,6,7-tetrahydro-3H-1-benzofuran-2-one
• CAS: 146451-40-3
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: VWOPTUCATATVGQ-ZMLRMANQSA-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

• 作为产物：
  描述：

  (3aS,4R,7aR)-4-Methyl-4-vinylhexahydrobenzofuran-2(3H)-one 在 咪唑 、 lithium aluminium tetrahydride 、 molecular sieve 、 四氯化钛 、 碳酸氢钠 、 间氯过氧苯甲酸 、 pyridinium chlorochromate 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (-)-7a-Epianastrephin
  参考文献：
  名称：

  mar（II）碘化物介导的还原环化方法可完全合成昆虫性引诱剂（-）-阿斯特拉芬

  摘要：

  在THF-HMPA中使用SmI 2有效地实现了对映体纯的γ，γ-差异C-取代的α，β-不饱和酯5的分子内还原环化，该酯具有末端醛官能团。从主要的环化产物6开始，（-）-anastrephin的对映体特异性全合成。1完成。

  DOI：

  10.1016/s0040-4039(00)74773-3

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）。
• Samarium(II) iodide-mediated reductive cyclization approach to total synthesis of the insect sex Attractant (−)-anastrephin
  作者：Kin-ichi Tadano、Yoshiaki Isshiki、Masaki Minami、Seiichiro Ogawa

  DOI：10.1016/s0040-4039(00)74773-3

  日期：1992.12

  C-substituted α,β-unsaturated ester 5 having a terminal aldehyde functionality, was effectively achieved using SmI2 in THF-HMPA. Starting with the major cyclization product 6, enantiospecific total synthesis of (−)-anastrephin. 1 was completed.

  在THF-HMPA中使用SmI 2有效地实现了对映体纯的γ，γ-差异C-取代的α，β-不饱和酯5的分子内还原环化，该酯具有末端醛官能团。从主要的环化产物6开始，（-）-anastrephin的对映体特异性全合成。1完成。
• Total syntheses of (-)-anastrephin, (-)-epianastrephin, and their 7a-epimers: use of samarium(II) iodide-mediated intramolecular reductive coupling for the construction of their hexahydrobenzofuran-2(3H)-one skeletons
  作者：Kinichi Tadano、Yoshiaki Isshiki、Masaki Minami、Seiichiro Ogawa

  DOI：10.1021/jo00075a021

  日期：1993.11

  D-Glucose-derived alpha,beta-unsaturated ester 17, which includes a geminally and differntially substituted gamma-carbon and a terminal aldehyde functionality, was subjected to a SMI2-Mediated intramolecular reductive coupling reaction in a THF solution containing 1/10 volume of HMPA. The reaction proceeded with moderate stereoselectivity to provide a diastereomeric mixture of hexahydrobenzofuran-2 (3H)-ones, in which cis-fused product 25 was obtained as the major isomer in 35% isolated yield. Two trans-fused coupling products 26 (17%) and 27 (14%) were also obtained. Starting from major product 25, the insect sex attractants (-)-anastrephin (1) and (-)-epianastrephin (2) were synthesized enantiospecifically. Two unnatural stereocongeners, (-)-7a-epi-anastrephin (3) and (-)-7a-epi-epianastrephin (4), were also derived from 25.