2-(4-iodobutyl)-1,3-dioxolane | 150238-91-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: 2-(4-iodobutyl)-1,3-dioxolane
• CAS: 150238-91-8
• 化学式: C₇H₁₃IO₂
• 分子量: 256.084
• InChiKey: TVOVDEARTZNLGD-UHFFFAOYSA-N

物化性质

• 沸点：
  259.5±15.0 °C(Predicted)
• 密度：
  1.598±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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-(4-iodobutyl)-1,3-dioxolane 在 盐酸 、 二甲基氯化铝 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 81.0h， 生成 2-(2-benzyl-1-oxo-2-azaspiro[5.5]undecan-7-yl)-N-methoxy-N-methylacetamide
  参考文献：
  名称：

  Construction of the Myrioneuron Alkaloids: A Total Synthesis of (±)-Myrioneurinol

  摘要：

  A strategy has been developed that culminated in a stereoselective total synthesis of the tetracyclic antimalarial Myrioneuron alkaloid myrioneurinol. The synthesis relies on three highly diastereoselective reactions, including an intramolecular chelation-controlled Michael spirocyclization of an N-Cbz-lactam titanium enolate to an alpha,beta-unsaturated ester for construction of the A/D-ring system and the attendant C5 (quaternary), C6 relative stereochemistry; a malonate enolate conjugate addition to a nitrosoalkene in order to install the appropriate functionality and establish the configuration at C7; and an intramolecular aza-Sakurai reaction to form the B-ring and the accompanying C9 and C10 stereocenters.

  DOI：

  10.1021/jo5026404
• 作为产物：
  描述：

  2-(4-氯丁基)-1,3-二氧戊环 在 sodium iodide 作用下， 以 丙酮 为溶剂， 以88%的产率得到2-(4-iodobutyl)-1,3-dioxolane
  参考文献：
  名称：

  Lithiated anions derived from (alkenyl)pentamethyl phosphoric triamides: Useful synthons for the stereoselective synthesis of 9-oxo- and 10-hydroxy-2(E)-decenoic acids, important components of queen substance and royal jelly of honeybee Apis mellifera

  摘要：

  Lithiated anions derived from (alkenyl) pentamethyl phosphoric triamides as homoenolate equivalents are used in the reaction with halogenated acetal and ketal giving regioselectively the gamma-alkylation adducts. Chemoselective acidic hydrolysis of the enephosphoramide moiety in the presence of acetal or ketal groups leads to expected carbonyl products, key intermediates in the synthesis of natural compounds. The synthetic potential of the presented strategy is illustrated by stereoselective synthesis of two pheromones namely, 9-oxo-2(E)-decenoic acid 1 from queen substance and 10-hydroxy-2(E)-decenoic acid 2 from royal jelly of honeybee Apis mellifera. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2010.06.020

文献信息

• Asymmetric Synthesis of Chiral Sulfoximines through the S‐Alkylation of Sulfinamides
  作者：Yusuke Aota、Taichi Kano、Keiji Maruoka

  DOI：10.1002/anie.201911021

  日期：2019.12.2

  bioisosteric groups. Chiral sulfoximines, which contain a tetrasubstituted sulfur atom that bears one nitrogen, one oxygen, and two different carbon substituents, represent an emerging chiral bioisostere in medicinal chemistry. Chiral sulfoximines are conventionally prepared by a stereospecific nitrene transfer reaction to chiral sulfoxides; however, the number of readily available chiral sulfoxides remains

  药物发现中的创新关键取决于新的生物等排团的发展。包含带有一个氮，一个氧和两个不同碳取代基的四取代硫原子的手性亚砜亚胺在药物化学中代表了一种新兴的手性生物等排体。手性亚砜亚胺通常通过立体定向的腈转移反应制备为手性亚砜。然而，容易获得的手性亚砜的数量仍然有限。在此，我们报道了迄今难以获得的具有两个结构相似的烷基链的手性亚磺酰亚胺类的不对称合成。我们的合成方法是基于在简单安全的条件下，使用市售试剂对易于获得的手性亚磺酰胺进行的硫选择性烷基化。
• New masked δ-lithiocarbonyl compounds: preparation and synthetic applications
  作者：Juan F. Gil、Diego J. Ramón、Miguel Yus

  DOI：10.1016/s0040-4020(01)80409-9

  日期：1993.5

  (1a–c) or 2-(4-chlorobutyl)-2-ethyl-1,3-dithiane (1d) with an excess of lithium powder and a catalytic amount of naphthalene (8 mol %) in THF at -78°C leads to a solution of the corresponding masked lithium δ-enolates 2, which react with different electrophiles (water, deuterium oxide, carbonyl compounds, carboxylic acid derivatives, dibenzyl disulfide or benzylideneaniline) to yield the expected products

  2-（4-氯丁基）-1,3-二氧戊环（1a–c）或2-（4-氯丁基）-2-乙基-1,3-二硫杂环丁烷（1d）与过量的锂粉和在-78°C下萘在THF中的催化量（8 mol％）导致相应的被掩盖的δ-烯醇锂2溶液，其与不同的亲电试剂（水，氘化氢，羰基化合物，羧酸衍生物，二苄基二硫化物）反应（或亚苄基苯胺）产生预期的产物3-15。在催化量的CuBr.Me 2 S存在下，中间体2a与环己-2-烯酮反应，通过共轭加成得到化合物16a。化合物10a的脱保护，12a，16a和4b–6b加上2 N HCl分别给出了预期的官能化羰基化合物17a–19a和20b–22b。最后，使用硅试剂，可以分别从原位生成的17a型羟醛与三乙基硅烷，烯丙基三甲基硅烷和三甲基甲硅烷基氰化物制备醇20a-25a，二烯醇26a-29a和氰基氧杂环戊烷30a-33a。
• Ligand-controlled NiH-catalyzed regiodivergent hydroalkylation of 2-alkenylazaarenes
  作者：Ya-Ping Shao、Zhuo-Min Chi、Yong-Min Liang

  DOI：10.1007/s11426-024-1949-1

  日期：2024.6

  azaarenes with alkyl iodines has been established through strategic modulation of N- or P-donor ligands. This method enables the synthesis of diverse β- or γ-branched aromatic N-heterocycles. The mild regiodivergent protocols exhibit wide substrate scope, excellent functional tolerance, and great reaction yield with remarkable regioselectivity. Importantly, deuterium labeling studies reveal NiH-catalyzed

  通过 N- 或 P- 供体配体的策略调节，建立了氢化镍 (NiH) 催化的 2-烯基氮杂芳烃与烷基碘的迁移和非迁移加氢烷基化反应。该方法能够合成多种β-或γ-支化芳香族N-杂环。温和的区域差异方案表现出广泛的底物范围、出色的功能耐受性、高反应产率和显着的区域选择性。重要的是，氘标记研究揭示了 NiH 催化的中断链行走模式是远程 β-选择性加氢烷基化反应背后的机制，这是一种通过芳香亚胺导向基团介导的有趣现象。
• Synthesis of juniperonic acid
  作者：Anders Vik、Trond Vidar Hansen、Anne Kristin Holmeide、Lars Skattebøl

  DOI：10.1016/j.tetlet.2010.03.085

  日期：2010.5

  Synthesis of juniperonic acid [(all-Z)-5,11,14,17-eicosatetraenoic acid], has been achieved in eight steps and in 19% overall yield starting from eicosapentaenoic acid. (C) 2010 Elsevier Ltd. All rights reserved.