(Z)-2-((5-iodopent-4-en-1-yl)oxy)tetrahydro-2H-pyran | 924889-40-7

• 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: (Z)-2-((5-iodopent-4-en-1-yl)oxy)tetrahydro-2H-pyran
• 英文别名: 2-(5-iodo-pent-4-enyloxy)-tetrahydropyran
• CAS: 924889-40-7
• 化学式: C₁₀H₁₇IO₂
• 分子量: 296.148
• InChiKey: YAERKECNVYBXKN-CLTKARDFSA-N

物化性质

• 沸点：
  312.9±42.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.26
• 重原子数：
  13.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (Z)-2-((5-iodopent-4-en-1-yl)oxy)tetrahydro-2H-pyran 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 对甲苯磺酸 、 二乙胺 作用下， 以 甲醇 为溶剂， 反应 13.0h， 生成 tridec-4-en-6-yn-1-ol
  参考文献：
  名称：

  Dicobaltoctacarbonyl-Mediated Synthesis of Tricyclic 5,6-Diydropyran-2-one Derivatives via Tandem Cycloaddition Reaction between cis-Epoxyalkynes, a Tethered Olefin, and Carbon Monoxide

  摘要：

  [GRAPHIC]Cobalt carbonyl complex Co-2(CO)(8) implemented an intramolecular carbonylation of cis-epoxyalkynes to generate Co-2(CO)(6)-stabilized gamma-lactonyl allene species. For 1,1,2-trisubstituted epoxyalkynes, this Co-2(CO)(6)-allene species reacted with a tethered olefin to give [2 + 2]-cycloadducts, and with CO and a tethered olefin to produce [2 + 2 + 1]-cycloadducts. These resulting cycloadducts have a 5,6-diydropyran-2-one core fused with a cyclobutane and a cyclopentanone ring, respectively. For 1,2-disubstituted cis-epoxyalkyne and 1,1,2-trisubstituted cis-epoxyalkynes bearing a heteroatom constituent, cyclization of the corresponding epoxyalkyne with a tethered alkene is invariably accompanied by incorporation of CO to produce a [2 + 2 + 1]-cycloadduct, even in the absence of CO. We have prepared various 1,1,2-trisubstituted and 1,2-disubstituted cis-epoxyalkynes to generalize such cycloaddition pathways. Attempt to use an organic promoter to perform these tandem cycloadditions was unsuccessful because of a competing Pauson-Khand reaction. Cyclization of a 1,2-disubstituted epoxyalkyne with a tethered diene was achieved successfully in one case, but the yield was low (25%).

  DOI：

  10.1021/jo0620617
• 作为产物：
  描述：

  4-(四氢-2H-吡喃-2-基氧基)丁醛 在 tris(dibenzylideneacetone)dipalladium (0) 、 三苯基膦 N-碘代丁二酰亚胺 、 三正丁基氢锡 、 sodium hexamethyldisilazane 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.25h， 生成 (Z)-2-((5-iodopent-4-en-1-yl)oxy)tetrahydro-2H-pyran
  参考文献：
  名称：

  Palladium-catalysed hydrostannylations of 1-bromoalkynes. A practical synthesis of (E)-1-stannylalk-1-enes

  摘要：

  重点介绍了一种包含多种氧和氮官能团的(E)-1-锡烷基-1-烯的实用合成方法，涉及1-溴炔的氢锡化反应，随后通过钯催化的碳-溴键断裂反应。

  DOI：

  10.1039/p19960002417

文献信息

• Enantioselective Aza-Sakurai Cyclizations: Dual Role of Thiourea as H-Bond Donor and Lewis Base
  作者：Yongho Park、Corinna S. Schindler、Eric N. Jacobsen

  DOI：10.1021/jacs.6b09736

  日期：2016.11.16

  An enantioselective, catalytic aza-Sakurai cyclization of chlorolactams has been developed as an efficient entry into indolizidine and quinolizidine frameworks. Structure-enantioselectivity relationship studies and mechanistic analysis point to a dual role of the catalyst wherein the thiourea moiety of the catalyst is engaged in both anion binding and Lewis base activation of a substrate.