rac-4-iodo-5-phenyldihydrofuran-2(3H)-one | 36598-07-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: rac-4-iodo-5-phenyldihydrofuran-2(3H)-one
• 英文别名: 4-iodo-5-phenyl-dihydrofuran-2-(3H)-one；(4R,5S)-4-iodo-5-phenyloxolan-2-one
• CAS: 36598-07-9；100238-89-9
• 化学式: C₁₀H₉IO₂
• 分子量: 288.085
• InChiKey: FARYFRZCCNUQHB-SCZZXKLOSA-N

物化性质

• 沸点：
  409.1±45.0 °C(Predicted)
• 密度：
  1.78±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  rac-4-iodo-5-phenyldihydrofuran-2(3H)-one 在 镍 、 异丙醇 作用下， 反应 0.25h， 以40%的产率得到γ-苯基-γ-丁内酯
  参考文献：
  名称：

  使用雷尼镍和 2-丙醇通过转移氢解脱碘内酯

  摘要：

  摘要 回流 2-丙醇中的雷尼镍是一种有效的催化体系，可将碘内酯还原为相应的内酯。

  DOI：

  10.1081/scc-120004856
• 作为产物：
  描述：

  反-苯乙烯乙酸 在 碘 、 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 以57 %的产率得到rac-4-iodo-5-phenyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  使用高价碘试剂简便合成 5-烷氧基-4-芳基四氢呋喃-2-酮

  摘要：

  γ-内酯用作合成多种天然产物和生物活性化合物的基础材料。本工作开发了一种γ位取代氧原子构建γ-内酯环的方法，该方法反应时间短，反应条件温和，操作简单，具有立体选择性。使用该反应，可以合成在γ位具有各种取代基（主要是卤代烷氧基）的γ-内酯环。

  DOI：

  10.1016/j.tetlet.2023.154382

文献信息

• Oxone^®-KI Induced Lactonization and Etherification of Unsaturated Acids and Alcohols: A Formal Synthesis of Mintlactone
  作者：M. Carla Marcotullio、Massimo Curini、Francesco Epifano、Francesca Montanari

  DOI：10.1055/s-2003-45009

  日期：——

  Unsaturated acids and alcohols interact with Oxone® and KI in acetonitrile-H 2 O and undergo iodolactonization and iodoetherification in short times with good yields. The reaction has been used for the formal synthesis ofmintlactone starting from isopulegol.

  不饱和酸和醇在乙腈-H 2 O 中与 Oxone® 和 KI 相互作用，并在短时间内以良好的产率进行碘内酯化和碘醚化。该反应已用于从异胡薄荷醇开始正式合成薄荷内酯。
• Are bis(pyridine)iodine(<scp>i</scp>) complexes applicable for asymmetric halogenation?
  作者：Daniel von der Heiden、Flóra Boróka Németh、Måns Andreasson、Daniel Sethio、Imre Pápai、Mate Erdelyi

  DOI：10.1039/d1ob01532j

  日期：——

  chiral trans-chelating bis(pyridine)iodine(I) complexes in the development of substrate independent, catalytic enantioselective halofunctionalization has been explored herein. Six novel chiral bidentate pyridine donor ligands have been designed, routes for their synthesis developed and their [N–I–N]+-type halogen bond complexes studied by 15N NMR and DFT. The chiral complexes encompassing a halogen

  对映体纯卤化分子作为合成中间体在药物、香料、香精、天然产物、杀虫剂和功能材料的构造中具有极其重要的作用。对映选择性卤代官能化仍然知之甚少，缺乏普遍适用的程序。本文探讨了手性反式螯合双(吡啶)碘( I )配合物在开发与底物无关的催化对映选择性卤代官能化中的适用性。设计了六种新型手性双齿吡啶供体配体，开发了它们的合成路线，并由15研究了它们的 [N-I-N] +型卤素键配合物N核磁共振和密度泛函。包含卤素键稳定的碘鎓离子的手性配合物显示能够有效地将碘鎓转移到烯烃；然而，没有对映选择性。立体选择性的缺乏被证明源于具有可比能量的多个配体构象的可用性和手性配体的空间影响不足。手性催化剂对底物的预组织似乎是对映选择性卤代官能化的必要条件。
• Tributylstannyl 4-tributylstannylbut-3-enoate: a useful C-4 homologating agent. Application to the synthesis of aryl iodolactones
  作者：Jérôme Thibonnet、Mohamed Abarbri、Jean-Luc Parrain、Alain Duchêne

  DOI：10.1016/0040-4039(96)01725-x

  日期：1996.10

  Tributylstannyl 4-tributylstannylbut-3-enoate, readily prepared by radical hydrostannation, is used for the transfer of a but-3-enoic acid synthon. Some of the potentialities of this synthon are established by the synthesis of aryl iodolactones or tetralones (one of them is a key intermediate for ABT-200 synthesis). Copyright (C) 1996 Published by Elsevier Science Ltd
• Microbially-Mediated Environmental Influences on Metazoan Colonization of Matground Ecosystems: Evidence from the Lower Cambrian Harkless Formation
  作者：J. V. BAILEY、F. A. CORSETTI、D. J. BOTTJER、K. N. MARENCO

  DOI：10.2110/palo.2005-p05-51e

  日期：2006.6.1

  Pro-Ordovician times, microbial mats may have covered large expanses of the continental shelf Evidence of mat-grounds in shallow-marine settings is provided by abundant wrinkle structures in Lower Cambrian strata of the Great Basin, United States. Wrinkle structures from the Lower Cambrian Harkless Formation commonly co-occur with a distinctive assemblage of invertebrate fossils, providing evidence for the possibility of selective metazoan colonization of matground substrates. Molds of linguliform brachiopods are abundant on many wrinkle surfaces. The agglutinated problematicum, Volborthella tenuis, also is found on wrinkle surfaces and in laminations beneath wrinkle-structure surfaces. Bedding-parallel trace fossils, such as Planolites, Diplichnites, and Taphrhelminthopsis, commonly crosscut wrinkle structures, while vertically oriented trace fossils are absent.Microbial mats containing layered microbial communities would have considerably compressed stratified redox zones beneath the sediment-water interface in marine-shelf settings. Sulfidic and anoxic conditions within and beneath Microbial mats would have precluded habitation by many mnetazoans, while those that adapted to such conditions may have found matgrounds a unique, though temporally fleeting, ecological niche. The distinctive, low-diversity fossil assemblage found in association with the wrinkle structures in the Great Basin suggests that some early animals may have been adapted to hypoxic and sulfidic conditions found in matground substrates, while others may have been physiologically excluded from these environments.
• Motohashi, Shigeyasu; Satomi, Masakichi; Fujimoto, Yasuo, Heterocycles, 1985, vol. 23, # 8, p. 2035 - 2039
  作者：Motohashi, Shigeyasu、Satomi, Masakichi、Fujimoto, Yasuo、Tatsuno, Takashi

  DOI：——

  日期：——