5-iodopentanoic acid | 19448-36-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-iodopentanoic acid
• 英文别名: 5-iodovaleric acid
• CAS: 19448-36-3
• 化学式: C₅H₉IO₂
• 分子量: 228.03
• InChiKey: RBFGSILNBZJPFI-UHFFFAOYSA-N

物化性质

• 熔点：
  56 °C
• 沸点：
  274.5±23.0 °C(Predicted)
• 密度：
  1.831±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-iodopentanoic acid 在 硼烷 、 sodium hydride 作用下， 生成 ethyl (2E)-7-iodohept-2-enoate
  参考文献：
  名称：

  Palladium-Catalyzed Diastereoselective Cyclization of the Allylic Precursors. A Concise Synthetic Route to 3-Azabicyclo[3.3.0]Octane and Hydroisoindole Skeletons

  摘要：

  A useful variant of palladium-catalyzed 1,2-diastereoselective cyclization of the allylic precursors based on the steric nature of the anion stabilizing groups has been developed. The 1,1,2-trisubstituted cycloalkane products have also been efficiently transformed into the azabicyclic systems.

  DOI：

  10.1080/00397910008087454
• 作为产物：
  描述：

  5-溴戊酸 在 氢碘酸 、 potassium hydrosulfide 作用下， 生成 5-iodopentanoic acid
  参考文献：
  名称：

  Koegl; de Man, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1941, vol. 269, p. 89

  摘要：

  DOI：

文献信息

• Cleavage of Carboxylic Esters by Aluminum and Iodine
  作者：Dayong Sang、Huaxin Yue、Yang Fu、Juan Tian

  DOI：10.1021/acs.joc.1c00034

  日期：2021.3.5

  A one-pot procedure for deprotecting carboxylic esters under nonhydrolytic conditions is described. Typical alkyl carboxylates are readily deblocked to the carboxylic acids by the action of aluminum powder and iodine in anhydrous acetonitrile. Cleavage of lactones affords the corresponding ω-iodoalkylcarboxylic acids. Aryl acetylates undergo deacetylation with the participation of the neighboring group

  描述了一种在非水解条件下使羧酸酯脱保护的一锅法方法。在无水乙腈中，铝粉和碘的作用下，典型的羧酸烷基酯很容易解封为羧酸。切割内酯得到相应的ω-碘代烷基羧酸。乙酸芳基酯在相邻基团的参与下进行脱乙酰化。该方法能够在芳基酯存在下选择性裂解烷基羧酸酯。
• Expedient Synthesis of Long-Chain ω-Substituted Fatty Acids and Esters from Cyclic Ketones Using Iodine and Hydrogen Peroxide
  作者：Viktor Zhdankin、Mekhman Yusubov、Ekaterina Podrezova、Maria Larkina、Mikhail Belousov、Andreas Kirschning

  DOI：10.1055/s-0036-1591598

  日期：2018.10

  convenient synthesis of ω-iodoaliphatic carboxylic acids and esters by the reaction of cyclic ketones with iodine and hydrogen peroxide in the presence of catalytic CuCl has been developed. ω-Iodoaliphatic carboxylic esters were further used for the efficient preparation of di(2-pyridylmethylamino)alkanoic acids in excellent yields. A simple and convenient synthesis of ω-iodoaliphatic carboxylic acids and

  摘要 已经开发了在催化CuCl存在下，通过环酮与碘和过氧化氢的反应，简单而方便地合成ω-碘代脂肪族羧酸和酯的方法。ω-碘代脂族羧酸酯还被用于以优异的产率有效地制备二（2-吡啶基甲基氨基）链烷酸。 已经开发了在催化CuCl存在下，通过环酮与碘和过氧化氢的反应，简单而方便地合成ω-碘代脂肪族羧酸和酯的方法。ω-碘代脂族羧酸酯还被用于以优异的产率有效地制备二（2-吡啶基甲基氨基）链烷酸。
• Efficient Synthesis of ω‐[ ¹⁸ F]Fluoroaliphatic Carboxylic Esters and Acids for Positron Emission Tomography
  作者：Mariia S. Larkina、Anastasia V. Ozerskaya、Ekaterina V. Podrezova、Mikhail V. Belousov、Vladimir Tolmachev、Viktor V. Zhdankin、Mekhman S. Yusubov

  DOI：10.1002/ejoc.202000934

  日期：2020.10.31

  The important PET tracers, ω‐[18F]fluoroaliphatic carboxylic acid derivatives, were prepared by nucleophilic radiofluorination of the readily available iodocarboxylic esters. Methyl 6‐[18F]fluorohexanoate was further applied as a starting material for the preparation of the succinimide ester (NHS ester)‐containing bifunctional radiofluorinated prosthetic group in two simple steps, 10 min each.

  重要的PET示踪剂是ω-[ 18 F]氟代脂族羧酸衍生物，是通过对易得的碘代羧酸酯进行亲核放射性氟化制备的。通过两个简单的步骤（每次10分钟），将6- [ 18 F]氟己酸甲酯进一步用作制备含琥珀酰亚胺酯（NHS酯）的双功能放射性氟化假体的原料。
• Catalytic Enantioselective Aldol Reactions of Unprotected Carboxylic Acids under Phosphine Oxide Catalysis
  作者：Shunsuke Kotani、Yusaku Yoshiwara、Masamichi Ogasawara、Masaharu Sugiura、Makoto Nakajima

  DOI：10.1002/anie.201810599

  日期：2018.11.26

  The first catalytic enantioselective aldol reaction of various unprotected carboxylic acids is described. In the presence of a chiral bis(phosphine oxide) as a Lewis base catalyst, carboxylic acids were activated with silicon tetrachloride to form the corresponding bis(trichlorosilyl)enediolates in situ, which subsequently underwent an aldol reaction with an aldehyde or a ketone to produce β‐hydroxycarboxylic

  描述了各种未保护的羧酸的第一催化对映选择性醛醇缩合反应。在手性双（氧化膦）作为路易斯碱催化剂的存在下，用四氯化硅活化羧酸以原位形成相应的双（三氯甲硅烷基）亚乙基二醇酯，随后将其与醛或酮进行醛醇缩合反应以生成高达92％ee的高对映选择性的β-羟基羧酸。
• Pyridazines, LXXII: On the Synthesis of Azinium and Diazinium Compounds Structurally Related to Pyridazomycin
  作者：Johnny Easmon、Gottfried Heinisch、Wolfgang Holzer、Barbara Matuszczak

  DOI：10.1002/ardp.19953280403

  日期：——

  series of pyridine‐, pyridazine‐, and pyrazine‐derived carboxamides bearing at the ring N‐atom an alkyl side‐chain with a terminal carboxylic group (7–11) or with a terminal acetylamino malonic ester moiety (13–17, 19–23) is described. Two desaza‐pyridazomycin derivatives (24, 26) and homologs thereof (25, 27) were synthesised. The novel compounds which are structurally related to the antifungal antibiotic

  制备一系列吡啶、哒嗪和吡嗪衍生的羧酰胺，在环 N 原子上带有一个烷基侧链，带有末端羧基 (7-11) 或末端乙酰氨基丙二酸酯部分 (13-17, 19-23) 进行了描述。合成了两种去氮杂-哒唑霉素衍生物 (24, 26) 及其同系物 (25, 27)。筛选了结构上与抗真菌抗生素哒嗪霉素相关的新化合物的抗真菌活性：初步体外试验显示没有活性。