4-iodohexahydro-benzofuran-2(3H)-one | 113335-95-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 4-iodohexahydro-benzofuran-2(3H)-one
• 英文别名: (3aS,7aS)-4-iodo-3a,4,5,6,7,7a-hexahydro-3H-1-benzofuran-2-one
• CAS: 113335-95-8；113335-96-9
• 化学式: C₈H₁₁IO₂
• 分子量: 266.079
• InChiKey: ZKKHPQMLIYXCKF-UYMSWOSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  4-iodohexahydro-benzofuran-2(3H)-one 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 4.0h， 生成 (3aS,7aS)-hexahydrobenzofuran-2(3H)-one
  参考文献：
  名称：

  Atom transfer cyclization reactions of .alpha.-iodo esters, ketones, and malonates: examples of selective 5-exo, 6-endo, 6-exo, and 7-endo ring closures

  摘要：

  DOI：

  10.1021/jo00274a034
• 作为产物：
  描述：

  2-cyclohexen-1-yl 2-iodoacetate 在 polystyrene resin supported (-CH₂O(CH₂)3Sn(Me₂)-)2 作用下， 以 苯 为溶剂， 反应 16.0h， 以90%的产率得到4-iodohexahydro-benzofuran-2(3H)-one
  参考文献：
  名称：

  Polymer-supported distannanes: a new and efficient synthesis of highly effective reagents for iodine atom transfer cyclisations

  摘要：

  Polymeric distannanes were synthesised by the cross-linking of polystyrene bound tin hydride functionalities using a palladium mediated dehydrogenative coupling. The polymers were characterised by spectroscopic methods (IR and C-13, Sn-119 NMR) and elemental analysis and were successfully applied to two iodine atom transfer cyclisations, performing as well as solution based hexaalkylditin reagents and significantly better than previously reported polymer-supported ditin reagents. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.11.039

文献信息

• A Novel Approach for the Formation of Carbon−Nitrogen Bonds:  Azidation of Alkyl Radicals with Sulfonyl Azides
  作者：Cyril Ollivier、Philippe Renaud

  DOI：10.1021/ja004129k

  日期：2001.5.1

  Two preparatively attractive methods for the azidation of alkyl radicals are described. Secondary and tertiary alkyl iodides and dithiocarbonates are easily converted into the corresponding azides, either by reaction with ethanesulfonyl azide in the presence of dilauroyl peroxide, or by treatment with benzenesulfonyl azide and hexabutylditin in the presence of a radical initiator. Interestingly, intramolecular

  描述了用于烷基基团叠氮化的两种制备性有吸引力的方法。通过在过氧化二月桂酰存在下与乙磺酰叠氮化物反应，或在自由基引发剂存在下用苯磺酰叠氮化物和六丁基二锡处理，仲和叔烷基碘和二硫代碳酸酯很容易转化为相应的叠氮化物。有趣的是，分子内串联自由基环化-叠氮化过程可以以高产率进行。
• Atom transfer cyclization reactions of α-iodo carbonyls
  作者：Dennis P. Curran、Chi-Tai Chang

  DOI：10.1016/s0040-4039(00)95445-5

  日期：1987.1
• Formation of Carbon−Nitrogen Bonds via a Novel Radical Azidation Process
  作者：Cyril Ollivier、Philippe Renaud

  DOI：10.1021/ja000673h

  日期：2000.7.1