methyl 6-iodohexanoate | 14273-91-7

• 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: methyl 6-iodohexanoate
• 英文别名: 6-iodo-hexanoic acid methyl ester
• CAS: 14273-91-7
• 化学式: C₇H₁₃IO₂
• 分子量: 256.084
• InChiKey: ZIASHHAADPIIDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  10
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P210,P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P332+P313,P337+P313,P362,P370+P378,P403+P233,P403+P235,P405,P501
• 危险性描述：
  H315,H319,H335,H227

反应信息

• 作为反应物：
  描述：

  methyl 6-iodohexanoate 在 palladium on activated charcoal 氢氧化钾 、 copper(l) iodide 、 lithium aluminium tetrahydride 、 三氯化铝 、 硫酸 、 氢溴酸 、 甲基锂 、 氢气 、 magnesium 作用下， 以 四氢呋喃 、 甲醇 、 水 、 溶剂黄146 、 甲苯 为溶剂， -78.0~25.0 ℃ 、399.99 kPa 条件下， 反应 109.0h， 生成 (R)-2-(9-phenylnonyl)pyrrolidine
  参考文献：
  名称：

  Enantioselective Total Synthesis of Irniine and Bgugaine, Bioactive 2-Alkylpyrrolidine Alkaloids

  摘要：

  An asymmetric total synthesis of the 2-(R)-alkylpyrrolidines, (-)-irniine (1a) and (-)-bgugaine (1b), toxic and antibiotic components of the tubers of Arisarum vulgare, and (+)-(S)-irniine (1c), was carried out by condensation of the corresponding 4-oxoalkanoic acid (9) with chiral phenylglycinol. Acids (9) were prepared from a hetero-organocuprate (I) complex, generated by reaction of methylcopper (I) with alkylmagnesium bromides and methyl chlorocarbonyl-propionate. Alkaloids (1a, 1b and 1c) displayed anti Gram(+) bacterial (MIC 12.5 - 50 mu g/ml) and antifungal (MIC 6.25 - 50 mu g/ml) activities.

  DOI：

  10.3987/com-95-7293
• 作为产物：
  描述：

  6-羟基己酸甲酯 在 咪唑 、 碘 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以61%的产率得到methyl 6-iodohexanoate
  参考文献：
  名称：

  Total Synthesis of the Eight Diastereomers of the Syn-Anti-Syn Phytoprostanes F₁ Types I and II

  摘要：

  Syntheses of the eight enantiomerically pure diastereomers of the syn-anti-syn phytoprostanes F-1 types I and II are described starting from D- and L-glucose. Key steps include Wittig coupling, Horner Wadsworth Emmons (HWE) reactions, and enantioselective reduction of alpha,beta-unsaturated ketones.

  DOI：

  10.1021/jo035638i

文献信息

• Prescreening of Nicotine Hapten Linkers in Vitro To Select Hapten-Conjugate Vaccine Candidates for Pharmacokinetic Evaluation in Vivo
  作者：Viswanath Arutla、Joseph Leal、Xiaowei Liu、Sriram Sokalingam、Michael Raleigh、Adejimi Adaralegbe、Li Liu、Paul R. Pentel、Sidney M. Hecht、Yung Chang

  DOI：10.1021/acscombsci.6b00179

  日期：2017.5.8

  (ELISA) to profile the interactions of nicotine haptens or hapten-protein conjugates with nicotine specific antibodies, both polyclonal and monoclonal. Another relies on computational modeling of the interactions between haptens and amino acid residues near the conjugation site of the carrier protein to infer linker-carrier protein conjugation effect on antinicotine antibody response. Using these two in

  自从证明尼古丁疫苗可作为治疗烟草烟雾影响的干预措施以来，人们为提高尼古丁特异性免疫力做出了巨大努力。尼古丁半抗原的接头修饰已成为改善尼古丁免疫原性的焦点，其中这些修饰的评估通常依赖于体内动物模型，例如小鼠，大鼠或非人灵长类动物。在这里，我们提出两种体外筛选策略，以评估和预测我们新设计的尼古丁半抗原的免疫原性。一种利用竞争性酶联免疫吸附测定法（ELISA）来分析尼古丁半抗原或半抗原-蛋白质缀合物与尼古丁特异性抗体（多克隆和单克隆）的相互作用。另一个依赖于半抗原与载体蛋白结合位点附近的氨基酸残基之间相互作用的计算模型，以推断接头-载体蛋白对抗烟碱抗体应答的结合作用。使用这两种体外方法，我们对具有不同连接子的半抗原作为有潜力的候选疫苗进行了排名。基于ELISA的半抗原排名与通过体内尼古丁药代动力学分析获得的结果一致。发现平均结合亲和力（IC 基于ELISA的半抗原排名与通过体内尼古丁药代动力学分
• Functional transformation of aldehydes and ketones via homolytic induced decomposition of unsaturated peroxy acetals and peroxy ketals
  作者：L. Moutet、D. Bonafoux、M. Degueil-Castaing、B. Maillard

  DOI：10.1039/a808418a

  日期：——

  Induced decomposition of unsaturated peroxy acetals prepared from trimethyl orthoformate, dodecanal or 2-methylundecanal and 2,3-dimethyl-2-hydroperoxybut-3-ene, in the presence of ethyl iodoacetate, CCl4 or dodecanethiol, allowed respectively their iodo-, chloro- and hydro- decarbonylation with yields of over 70%; the same reaction applied to the monoperoxy ketal or diperoxy ketal of cyclohexanone in the presence of ethyl iodoacetate resulted in its functional transformation in methyl 6-iodohexanoate or 1,5-diiodopentane with respective yields of 65 and 40%.

  通过三甲基原甲酸酯、十二醛或2-甲基十一醛和2,3-二甲基-2-羟过氧丁-3-烯在乙基碘乙酸酯、CCl4或十二硫醇的存在下引发的未饱和过氧缩醛的分解反应，分别实现了它们的碘代、氯代和羟基脱羰反应，产率均超过70%；同样的反应在乙基碘乙酸酯存在下应用于环己酮的单过氧缩酮或双过氧缩酮，分别得到了甲基6-碘己酸酯或1,5-二碘戊烷，产率分别为65%和40%。
• 8,12-Dialkyl-PGE, and PGF.sub.1.sub..alpha.
  申请人：The Upjohn Company

  公开号：US03953499A1

  公开（公告）日：1976-04-27

  Prostaglandins E.sub.1 -type and F.sub.1 -type compounds of the formula ##EQU1## wherein R is hydrogen or a hydrocarbyl group containing from 1 to 12 carbon atoms, inclusive, wherein W is ##EQU2## or O =, wherein R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11, R.sub.12, R.sub.13, and R.sub.14 are hydrogen or alkyl of 1 to 4 carbon atoms, inclusive, provided (1) that at least one of R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11, R.sub.12, R.sub.13, and R.sub.14 is alkyl (2) that when R.sub.13 is alkyl, at least one of R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11, R.sub.12, and R.sub.14 is alkyl, and (3) that when R.sub.7 is alkyl or thwn R.sub.7 and R.sub.8 are alkyl, at least one of R.sub.9, R.sub.10, R.sub.11, R.sub.12, R.sub.13, and R.sub.14 is alkyl; and the enantiomers and racemic mixtures thereof. These are useful for the same pharmacological purposes as the unsubstituted prostaglandins.

  前列腺素E.sub.1-型和F.sub.1-型化合物的化学式为##EQU1##其中R为氢或含有1至12个碳原子的烃基，其中W为##EQU2##或O=，其中R.sub.7、R.sub.8、R.sub.9、R.sub.10、R.sub.11、R.sub.12、R.sub.13和R.sub.14为氢或1至4个碳原子的烷基，满足以下条件：(1)至少有一个R.sub.7、R.sub.8、R.sub.9、R.sub.10、R.sub.11、R.sub.12、R.sub.13和R.sub.14为烷基；(2)当R.sub.13为烷基时，至少有一个R.sub.7、R.sub.8、R.sub.9、R.sub.10、R.sub.11、R.sub.12和R.sub.14为烷基；(3)当R.sub.7为烷基或R.sub.7和R.sub.8为烷基时，至少有一个R.sub.9、R.sub.10、R.sub.11、R.sub.12、R.sub.13和R.sub.14为烷基；以及它们的对映体和消旋混合物。这些化合物可用于与未取代前列腺素相同的药理目的。
• Fenton-Inspired C–H Functionalization: Peroxide-Directed C–H Thioetherification
  作者：Brian J. Groendyke、Atanu Modak、Silas P. Cook

  DOI：10.1021/acs.joc.9b01979

  日期：2019.10.18

  catalytic amount of iron(II) triflate, TIPS-protected peroxides bearing primary, secondary, and tertiary C-H sites undergo chemoselective thioetherification of remote C-H bonds with diaryl disulfides. The reaction demonstrates a broad substrate scope and functional group tolerance without the use of any noble metal additives. Mechanistic experiments suggest that the reaction proceeds through 1,5-H atom

  亚化学计量的铁介导了常驻甲硅烷基过氧化物指导的未活化脂族CH键的硫醚化作用。暴露于催化量的三氟甲磺酸铁（II）后，带有伯，仲和叔CH位的TIPS保护的过氧化物会通过二芳基二硫化物对远端CH键进行化学选择性硫醚化。该反应证明了广泛的底物范围和官能团耐受性，而无需使用任何贵金属添加剂。机理实验表明，反应是通过铁生成的羟基自由基通过1，5-H原子提取而进行的。
• Transition Metal Free Stannylation of Alkyl Halides: The Rapid Synthesis of Alkyltrimethylstannanes
  作者：Songyi Li、Chang Lian、Guanglu Yue、Jianning Zhang、Di Qiu、Fanyang Mo

  DOI：10.1021/acs.joc.1c03135

  日期：2022.3.18

  A transition metal free stannylation reaction of alkyl bromides and iodides with hexamethyldistannane has been developed. This protocol is operationally convenient and features a rapid reaction and good functional group tolerance. A wide range of functionalized primary and secondary alkyl and benzyl trimethyl stannanes are prepared in moderate to excellent yields. The success of the gram-scale procedure

  已经开发了烷基溴化物和碘化物与六甲基二锡烷的无过渡金属的锡烷基化反应。该协议操作方便，反应速度快，官能团耐受性好。以中等至优异的产率制备了范围广泛的官能化伯和仲烷基和苄基三甲基锡烷。克级程序和串联 Stille 偶联反应的成功使该协议展示了在有机合成中的应用潜力。实验和理论研究都揭示了这种酸化反应的机理细节。