2-<(7-Iodo-5-heptynyl)oxy>-2H-tetrahydropyran | 31703-58-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 2-<(7-Iodo-5-heptynyl)oxy>-2H-tetrahydropyran
• 英文别名: 1-iodo-7-(α-tetrahydropyranyl)oxy-2-heptyne；1-iodo-7-(α-tetrahydropyranyloxy)-2-heptyne；1-iodo-7-(tetrahydropyranyloxy)-2-heptyne；2-(7-iodo-hept-5-ynyloxy)-tetrahydro-pyran；2-(7-Iodohept-5-ynoxy)oxane
• CAS: 31703-58-9
• 化学式: C₁₂H₁₉IO₂
• 分子量: 322.186
• InChiKey: ZEQYKRNONYATTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-<(7-Iodo-5-heptynyl)oxy>-2H-tetrahydropyran 在 copper(I) bromide dimethylsulfide complex 、 nickel diacetate 、 乙二胺 咪唑 、 sodium tetrahydroborate 、 四溴化碳 、 乙基溴化镁 、 氢气 、 铬酸 、 对甲苯磺酸 、 三苯基膦 作用下， 以 甲醇 为溶剂， 生成 (10-methoxycarbonyldeca-3,6-cis,cis-dienyl)-triphenylphosphonium bromide
  参考文献：
  名称：

  The total synthesis of 15(S)-HPETE (hydroperoxyeicosatetraenoic acid)

  摘要：

  The total synthesis of 15(S)-HPETE in enantiomerically pure form is achieved through C=C bond formation in the presence of a masked hydroperoxide. Selective reduction of a peracid in the presence of a hydroperoxide affords a mild method for removal of an HPETE methyl ester.

  DOI：

  10.1021/jo00033a006
• 作为产物：
  描述：

  7-(tetrahydro-2H-pyran-2-yloxy)hept-2-yn-1-ol 在 咪唑 、 碘 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以72%的产率得到2-<(7-Iodo-5-heptynyl)oxy>-2H-tetrahydropyran
  参考文献：
  名称：

  A Chemoenzymic Approach to Hydroperoxyeicosatetraenoic Acids. Total Synthesis of 5(S)-HPETE

  摘要：

  A new synthetic approach to enantiomerically pure hydroperoxyeicosatetraenoic acids (HPETEs) is described in which the tetraene skeleton is assembled through chemoselective olefination of a protected hydroperoxy aldehyde. Soybean lipoxygenase-mediated dioxygenation of both natural and unnatural fats produces hydroperoxy dienes in high enantiomeric excess; the observed regioselectivity supports a revised hypothesis for substrate specificity. Protection of the diene hydroperoxides as peroxy ketals is followed by regioselective ozonolysis to afford enantiomerically pure 4-peroxy 2,3-enals which undergo olefination to produce peroxytetraenoates. Removal of the monoperoxy ketal and the methyl ester affords enantiomerically pure HPETEs. The generality of the strategy is illustrated with the first chemical synthesis of 5(S)-HPETE.

  DOI：

  10.1021/jo00106a037

文献信息

• Facile retro Diels–Alder reaction of a pentamethyltricyclo[5.2.1.0^2,6]decenone derivative: synthesis of (+)-15(S)-prostaglandin A₂
  作者：Paul A. Grieco、Norman Abood

  DOI：10.1039/c39900000410

  日期：——

  The incorporation of methyl groups into the C(1), C(7), C(8), C(9), and C(10) positions of tricyclo[5.2.1.02,6]decenone (1) dramatically accelerates the retro Diels–Alder reaction of (3) under Lewis acid catalysis thus permitting access to synthetic natural prostaglandin A2; the X-ray crystal structure of the ammonium salt of (7) is reported.

  三环[5.2.1.0 2,6 ]癸烯酮（1）的C（1），C（7），C（8），C（9）和C（10）位置上甲基的结合显着加速了（3）在路易斯酸催化下的Diels-Alder逆反应，因此可以使用合成的天然前列腺素A 2；报告了（7）的铵盐的X射线晶体结构。
• A Synthesis of <i>d,l</i>-Prostaglandin E₂ Methyl Ester and Related Compounds
  作者：E. S. Ferdinandi、G. Just

  DOI：10.1139/v71-177

  日期：1971.4.1

  A synthesis of d,l-prostaglandin E2 (PGE2) methyl ester is described. Two new acetylenic prostaglandins, methyl 11α,15-dihydroxy-9-oxo-prost-5-yn-13-enoate and its C15 epimer, were obtained as intermediates in this synthesis. A solvolytic rearrangement of a bicyclo[2.1.0]hexane to a cyclopentane vinyl system is discussed.

  描述了 d,l-前列腺素 E2 (PGE2) 甲酯的合成。获得了两种新的炔类前列腺素，甲基 11α,15-dihydroxy-9-oxo-prost-5-yn-13-enoate 及其 C15 差向异构体，作为该合成的中间体。讨论了双环 [2.1.0] 己烷溶剂分解重排为环戊烷乙烯基体系。
• Lis, L. G.; Zheldakova, T. A.; Pap, A. A., Journal of Organic Chemistry USSR (English Translation), 1992, vol. 28, # 9.1, p. 1485 - 1490
  作者：Lis, L. G.、Zheldakova, T. A.、Pap, A. A.、Lakhvich, F. A.

  DOI：——

  日期：——
• Lis, L. G.; Filich, E. R.; Zheldakova, T. A., Journal of Organic Chemistry USSR (English Translation), 1992, vol. 28, # 10, p. 1654 - 1658
  作者：Lis, L. G.、Filich, E. R.、Zheldakova, T. A.、Pap, A. A.、Lakhvich, F. A.

  DOI：——

  日期：——
• GRIECO, PAUL A.;ABOOD, NORMAN, J. CHEM. SOC. CHEM. COMMUN.,(1990) N, C. 410-412
  作者：GRIECO, PAUL A.、ABOOD, NORMAN

  DOI：——

  日期：——