isopropyl 2-(4-iodophenoxy)-2-methylpropanoate | 1375008-18-6

• 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: isopropyl 2-(4-iodophenoxy)-2-methylpropanoate
• 英文别名: Propan-2-yl 2-(4-iodophenoxy)-2-methylpropanoate
• CAS: 1375008-18-6
• 化学式: C₁₃H₁₇IO₃
• 分子量: 348.181
• InChiKey: YPMKNJOMGTUZEE-UHFFFAOYSA-N

物化性质

• 沸点：
  351.4±22.0 °C(Predicted)
• 密度：
  1.460±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  isopropyl 2-(4-iodophenoxy)-2-methylpropanoate 、 9-methyl-9H-fluorene-9-carbonyl chloride 在 dichloro(cycloocta-1,5-diene)palladium (II) 、 N-甲基二环己基胺 、 potassium formate 、 四丁基碘化铵 、 tricyclohexylphosphine tetrafluoroborate 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以91%的产率得到isopropyl 2-(4-formylphenoxy)-2-methylpropanoate
  参考文献：
  名称：

  Reductive Carbonylation of Aryl Halides Employing a Two-Chamber Reactor: A Protocol for the Synthesis of Aryl Aldehydes Including ¹³C- and D-Isotope Labeling

  摘要：

  A protocol has been developed for conducting the palladium-catalyzed reductive carbonylation of aryl iodides and bromides using 9-methylfluorene-9-carbonyl chloride (COgen) as a source of externally delivered carbon monoxide in a sealed two-chamber system (COware), and potassium formate as the in situ hydride source. The method is tolerant to a wide number Of functional groups positioned on the aromatic ring, and it can be exploited for the isotope labeling of the aldehyde group. Hence, reductive carbonylations run with (13)COgen provide a facile access to C-13-labeled aromatic aldehydes, whereas with DCO2K, the aldehyde is specifically labeled with deuterium. Two examples of double isotopic labeling are also demonstrated. Finally, the method was applied to the specific carbon-13 labeling of the beta-amyloid binding compound, florbetaben.

  DOI：

  10.1021/jo400741t
• 作为产物：
  描述：

  2-溴异丁酸异丙酯 、 4-碘苯酚 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以36%的产率得到isopropyl 2-(4-iodophenoxy)-2-methylpropanoate
  参考文献：
  名称：

  可控的单和双二氟亚甲基插入 C-Cu 键：铜介导的芳基碘与 TMSCF2H 和 TMSCF2Br 的四氟乙基化和六氟丙基化

  摘要：

  选择性地将二氟亚甲基插入 C-Cu 键是一项具有挑战性的任务，目前仅限于单 CF 2插入 CuCF 3或双 CF 2插入 CuC 6 F 5（或 ( Z )-CF 3 CF = CFCu） . 在相同的 C-Cu 键中实现选择性单和双 CF 2插入甚至更加困难。在此，已经描述了使用 TMSCF 2 Br 试剂将高度可控的单和双 CF 2插入到 CuCF 2 H 物质中，提供了两种以前未知的氟烷基铜物质“Cu(CF 2 ) nCF 2 H” ( n = 1 和 2) 在不同反应条件下独立。这项工作代表了单和双 CF 2以高选择性方式插入同一 C-Cu 键的第一个例子。所获得的“Cu(CF 2 ) n CF 2 H” ( n = 1 和 2) 物质的合成价值通过它们与芳基碘、卤化剂和肉桂酰氯的反应来证明，这使得 HCF 2 CF的直接转移成为可能2和HCF 2 CF 2 CF 2部分变成有机分子。碳氟化合物链可控伸长率的关键1到

  DOI：

  10.1021/jacs.2c03104

文献信息

• Palladium Catalyzed Carbonylative Heck Reaction Affording Monoprotected 1,3-Ketoaldehydes
  作者：Thomas M. Gøgsig、Dennis U. Nielsen、Anders T. Lindhardt、Troels Skrydstrup

  DOI：10.1021/ol300837d

  日期：2012.5.18

  The direct carbonylative palladium catalyzed synthesis of monoprotected 1,3-ketoaldehydes is reported starting from aryl iodides applying near stoichiometric amounts of carbon monoxide. Besides representing platforms for a variety of heterocyclic structures, these motives serve as viable precursors for the highly relevant aryl methyl ketones. The presented strategy can also be adapted for the facile

  据报道，从芳基碘化物开始以接近化学计算量的一氧化碳开始，直接羰基钯催化的单保护的1，3-酮醛的羰基钯催化合成。这些动机除了代表各种杂环结构的平台外，还用作高度相关的芳基甲基酮的可行前体。所提出的策略也可以适用于13 C标记的一氧化碳的简便有效结合。
• ¹⁴Carbon monoxide made simple - novel approach to the generation, utilization, and scrubbing of¹⁴carbon monoxide
  作者：Anders T. Lindhardt、Roger Simonssen、Rolf H. Taaning、Thomas M. Gøgsig、Göran N. Nilsson、Gunnar Stenhagen、Charles S. Elmore、Troels Skrydstrup

  DOI：10.1002/jlcr.2962

  日期：2012.9

  A new method is reported for the efficient generation of 14CO that can be applied in transition metal-catalyzed carbonylation reactions. 14CO is produced by palladium-catalyzed decarbonylation of the stable acid chloride, 14COgen. When combined in a two-chamber system, the produced 14CO is incorporated into the target molecule with high efficiency. As the carbonylation chemistry is performed under mild conditions, this allows the 14C isotope to enter the synthesis into an advanced stage intermediate. The presented work includes two aminocarbonylations, one amidocarbonylation, and one carbonylative Suzuki–Miyaura coupling, all installing the 14C isotope in the final step of the synthesis. Finally, the identification of a highly efficient scrubber for the safe trapping and removal of any leftover 14CO is also disclosed.

  报道了一种高效生成适用于过渡金属催化的羰基化反应的14CO的新方法。14CO是通过钯催化的稳定酰氯14COgen的去羰基化反应生成的。在双室系统中结合使用时，生成的14CO高效地被整合到目标分子中。由于羰基化反应是在温和条件下进行的，这使得14C同位素能够进入合成的高级中间体阶段。所述工作包括两种氨基羰基化、一种酰胺羰基化和一种羰基化Suzuki-Miyaura偶联，所有这些都在合成的最后一步引入14C同位素。最后，还披露了一种高效的安全捕集和移除任何剩余14CO的洗涤器。
• Ligand‐free Palladium‐Catalyzed Carbonylative Suzuki Coupling of Aryl Iodides in Aqueous CH ₃ CN with Sub‐stoichiometric Amount of Mo(CO) ₆ as CO Source
  作者：Nan Sun、Qingxia Sun、Wei Zhao、Liqun Jin、Baoxiang Hu、Zhenlu Shen、Xinquan Hu

  DOI：10.1002/adsc.201900011

  日期：2019.4.23

  established based on the palladium‐catalyzed carbonylative Suzuki coupling approach with sub‐stoichiometric Mo(CO)6 as CO source. Using 0.5 mol% of Pd(TFA)2 as catalyst, 0.5 equivalent of Mo(CO)6 as solid carbonyl reagent and 3 equivalent of K3PO4 as base, a wide range of functionalized (hetero)aryl iodides and (hetero)aryl boronic acids could smoothly proceed the carbonylative cross‐coupling reaction in aqueous

  基于亚化学计量的Mo（CO）6作为CO源的钯催化羰基化Suzuki偶联方法，已经建立了一种合成二芳基和杂二芳基酮的新方法。使用0.5摩尔％的Pd（TFA）2作为催化剂，0.5当量的Mo（CO）6作为固体羰基试剂和3当量的K 3 PO 4作为碱，各种官能化的（杂）芳基碘和（杂）芳基硼酸可以在50°C的CH 3 CN水溶液中平稳地进行羰基交叉偶联反应，从而提供相应的酮，收率非常好。新开发的方法易于在温和条件下高效地操作。
• Integrative Photoreduction of CO₂ with Subsequent Carbonylation: Photocatalysis for Reductive Functionalization of CO₂
  作者：Xing He、Yu Cao、Xian-Dong Lang、Ning Wang、Liang-Nian He

  DOI：10.1002/cssc.201801621

  日期：2018.10.11

  conversion of CO2 into fuels and chemicals with solar energy would be promising, but also faces great challenge. In this context, we describe the photoreductive functionalization of CO2 to construct new C−C, C−N, and C−O bonds through the respective Pd‐catalyzed Suzuki carbonylation, aminocarbonylation, and alkoxycarbonylation of aryl iodides with CO in situ generated through the photoreduction of CO2. This

  利用太阳能将CO 2有效地转化为燃料和化学物质将是有希望的，但同时也面临着巨大的挑战。在这种情况下，我们描述了CO 2的光还原功能化，通过相应的Pd催化的芳基碘化物的Pd催化的Suzuki羰基化，氨基羰基化和烷氧基羰基化，通过原位生成CO来构建新的C C，C N和C O键。 CO 2的光还原。该协议通过利用太阳能为CO 2利用开辟了一条替代途径。
• Transition-metal-free, ambient-pressure carbonylative cross-coupling reactions of aryl halides with potassium aryltrifluoroborates
  作者：Fengli Jin、Wei Han

  DOI：10.1039/c5cc01968k

  日期：——

  We disclose an unprecedented transition-metal-free carbonylative cross coupling of aryl halides with potassium aryl trifluoroborates even at atmospheric pressure of carbon monoxide. This protocol is efficient, operationally simple, and shows...

  我们公开了空前的无过渡金属的芳基卤化物与芳基三氟硼酸钾的无过渡金属羰基交叉偶合，即使在一氧化碳的大气压下也是如此。该协议高效，操作简单，并显示...