11-iodoundec-1-yne | 2468-57-7

• 分子结构分类: 有机化合物 - 乙炔化物
• 英文名称: 11-iodoundec-1-yne
• 英文别名: 11-iodo-1-undecyne；11-Iod-undecin-1
• CAS: 2468-57-7
• 化学式: C₁₁H₁₉I
• 分子量: 278.176
• InChiKey: COWWYFOFCMTKHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  12
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  11-iodoundec-1-yne 在 吡啶 、 氧气 、 sodium hydride 、 三乙胺 、 nickel(II) nitrate 、 copper dichloride 作用下， 以 甲醇 、 甲苯 、 mineral oil 为溶剂， 反应 15.0h， 生成
  参考文献：
  名称：

  Phase Separation As a Strategy Toward Controlling Dilution Effects in Macrocyclic Glaser-Hay Couplings

  摘要：

  Macrocycles are abundant in numerous chemical applications, however the traditional strategy for the preparation of these compounds remains cumbersome and environmentally damaging; involving tedious reaction set-ups and extremely dilute reaction media. The development of a macrocyclization strategy conducted at high concentrations is described which exploits phase separation of the catalyst and substrate, as a strategy to control dilution effects. Sequestering a copper catalyst in a highly polar and/or hydrophilic phase can be achieved using a hydrophilic ligand, T-PEG(1900), a PEGylated TMEDA derivative. Similarly, phase separation is possible when suitable copper complexes are soluble in PEG(400), a green and efficient solvent which can be utilized in biphasic mixtures for promoting macrocyclization at high concentrations. The latter phase separation technique can be exploited for the synthesis of a wide range of industrially relevant macrocycles with varying ring sizes and functional groups.

  DOI：

  10.1021/ja208902t
• 作为产物：
  描述：

  undec-10-yn-1-yl methanesulfonate 在 sodium iodide 作用下， 以 丁酮 为溶剂， 反应 24.0h， 以75%的产率得到11-iodoundec-1-yne
  参考文献：
  名称：

  Preparation of biological labels with acetylenic linker arms

  摘要：

  The preparation of a series of fluorescent labels based on acridone, pyrene, fluorescein, dimedlylaminonaphthalenesulphonamide and tris-l,10-phenanthroline ruthenium and an enzymic label based on biotin with spacers containing a terminal acetylene is described. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(96)01084-8

文献信息

• Copper‐Catalyzed Difluoromethylation of Alkyl Iodides Enabled by Aryl Radical Activation of Carbon–Iodine Bonds
  作者：Aijie Cai、Wenhao Yan、Chao Wang、Wei Liu

  DOI：10.1002/anie.202111993

  日期：2021.12.20

  An aryl radical activation strategy has been developed that can engage unactivated alkyl iodides in copper-catalyzed Negishi-type cross-coupling reactions. The strategy is based on the largely overlooked yet highly efficient reactivity of aryl radicals to abstract iodine atoms from alkyl iodides.

  已经开发出一种芳基自由基活化策略，可以在铜催化的 Negishi 型交叉偶联反应中使用未活化的烷基碘。该策略基于芳基自由基从烷基碘化物中提取碘原子的很大程度上被忽视但高效的反应性。
• Prodigiosenes conjugated to tamoxifen and estradiol
  作者：Estelle Marchal、Carlotta Figliola、Alison Thompson

  DOI：10.1039/c7ob00943g

  日期：——

  We report the synthesis of the first click-appended prodigiosene conjugates. Four prodigiosene conjugates of estradiol functionalised at the 7α-position were prepared, as were three prodigiosene conjugates of tamoxifen. The coupling between a prodigiosene and an 11-hydroxy estradiol derivative via an ether linkage was investigated, as was the 11- and 7-functionalisation of the estradiol core. The robustness

  我们报告的第一个单击追加prodigiosene共轭物的合成。制备了在7α-位官能化的四种雌二醇的前黄花共轭物，以及他莫昔芬的三种前黄花共轭物。dig和11-羟基雌二醇衍生物之间的偶联通过研究了醚键，以及雌二醇核心的11-和7-官能化。雌二醇保护基团的稳健性受到通常用于为11和7官能化的这类骨架装备的反应的严峻挑战。特别是，对于涉及雌二醇的合成而言，TBS，TMS和THP对合成至关重要，对于该核心的功能化而言，它不是有用的保护基。当治疗剂的化学特征限制了保护基团的选择（在这种情况下，带有芳基，NH，烯基和酯基的pro二烯），点击化学就成为一种有吸引力的合成策略。评估了七种单击的前黄酮共轭物的抗癌活性。
• New myocardial imaging agents: stabilization of radioiodine as a terminal vinyl iodide moiety on tellurium fatty acids
  作者：F. F. Knapp、M. M. Goodman、A. P. Callahan、L. A. Ferren、G. W. Kabalka、K. A. R. Sastry

  DOI：10.1021/jm00363a014

  日期：1983.9

  To determine the myocardial uptake and retention properties of radioiodinated tellurium fatty acids, we prepared two new tellurium fatty acids in which iodine-125 has been chemically stabilized by attachment as a trans-vinyl iodide (I-CH = CH-R-Te-R'-COOH) and evaluated them in rats. Fabrication of 18-iodo-13-tellura-17-octadecenoic acid was accomplished by coupling 1,5-diiodo-1-pentene with sodium

  为了确定放射性碘化碲脂肪酸的心肌摄取和保留特性，我们制备了两种新的碲脂肪酸，其中碘125已通过附着作为反乙烯基碘而化学稳定（I-CH = CH-R-Te-R '-COOH），并在大鼠中对其进行了评估。通过将1，5-二碘-1-戊烯与12-（甲氧基羰基）-n-十二烷基-1-基碲化钠偶联来完成18-碘-13-碲-十七-十八烯酸的制备。[5-125I] -1,5-二碘-1-戊烯是通过有机硼烷技术制备的，该技术涉及125I +处理5-碘-1-戊-1-基硼酸[I（CH2）3CH = CHB（OH）2 ]。该药物的绝对心脏摄取量中等（60分钟后为1.47-2.52％剂量/克），但心脏/血液比率较低（约2.6：1）。仅发生体内边缘脱碘，因为甲状腺摄取量低（60分钟后剂量为15-18％/ g）。碲在位置13的影响是出乎意料的。为了确定低心脏特异性和低心/血比是否取决于碲的位置，我们制备了具有相同链长的类似物18-
• The first total synthesis of 15-epi-annonin I
  作者：Ingo Wöhrle、Arno Claßen、Marcus Peterek、Hans-Dieter Scharf

  DOI：10.1016/0040-4039(96)01589-4

  日期：1996.9

  The first total synthesis of the 15-epimer 1b of the naturally occurring acetogenin annonin I 1a is described. All stereogenic centres in the bis-THF subunit are controlled via successive Sharpless asymmetric epoxidations (AE). Alkyl side chains were attached directly to the core using alkyne-epoxide couplings.

  描述了天然存在的产乙酸甘油酯Annnonin I 1a的15-受体1b的第一全合成。通过连续的Sharpless不对称环氧化（AE）控制bis-THF亚基中的所有立体异构中心。使用炔烃-环氧偶联剂将烷基侧链直接连接到核上。
• Threading of various ‘U’ shaped bidentate axles into a heteroditopic macrocyclic wheel via Ni^II/Cu^II templation
  作者：Mandira Nandi、Saikat Santra、Bidyut Akhuli、Pradyut Ghosh

  DOI：10.1039/c7dt00699c

  日期：——

  functionalities (Axle1-Axle10) is investigated by using a heteroditopic amido-amine macrocyclic (MC) wheel via NiII or CuII metal ion templation. These bent shaped axles are the derivatives of 4, 4' substituted 2, 2' bipyridine, which are composed of various terminal groups like alkene, alkyne, bromide, hydroxyl and azide. Such metallo [2]pseudorotaxanes are well characterised by ESI-MS, EPR and FT-IR spectroscopic

  通过使用异二位酰胺基胺大环（MC）轮，通过NiII或CuII金属离子模板，研究了具有各种功能（Axle1-Axle10）的“ U”形弯轴的螺纹。这些弯曲的轴是4、4'取代的2、2'联吡啶的衍生物，它们由各种末端基团组成，如烯烃，炔烃，溴化物，羟基和叠氮化物。尽可能通过ESI-MS，EPR和FT-IR光谱研究，UV-Vis吸收研究，元素分析和单晶X射线衍射研究对此类金属[2]假轮烷进行了很好的表征。实验证据支持MC，金属离子和轴之间的1：1：1三元络合。三种CuII模板化三元配合物（PR1'，PR3'和PR7'的单晶X射线结构 ）显示了模板金属离子周围的五配位排列。有趣的是，在互补的车轮和车轴组件中明智地选择化学功能可以显示各种共价和非共价相互作用的存在。