1,16-diiodohexadecane | 24772-67-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机碘化物
• 英文名称: 1,16-diiodohexadecane
• CAS: 24772-67-6
• 化学式: C₁₆H₃₂I₂
• 分子量: 478.239
• InChiKey: PELBSTYGIAZBMM-UHFFFAOYSA-N

物化性质

• 熔点：
  55-56 °C
• 沸点：
  427.3±13.0 °C(Predicted)
• 密度：
  1.447±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  18
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  1,16-diiodohexadecane 在 乙醚 、 二丁醚 、 氢碘酸 、 sodium 、 potassium n-butoxide 、 正丁醇 作用下， 生成 1,22-diiododocosane
  参考文献：
  名称：

  Assessments for the courts: A survey of Australian psychologists

  摘要：

  DOI：

  10.1080/13218710009524981
• 作为产物：
  描述：

  16-溴-1-十六烷醇 在 四溴化碳 、 三苯基膦 、 sodium iodide 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 16.0h， 生成 1,16-diiodohexadecane
  参考文献：
  名称：

  Conformationally-locked N-glycosides: Exploiting long-range non-glycone interactions in the design of pharmacological chaperones for Gaucher disease

  摘要：

  Pyranoid-type glycomimetics having a cis-1,2-fused glucopyranose-2-alkylsulfany1-1,3-oxazoline (Glc-PSO) structure exhibit an unprecedented specificity as inhibitors of mammalian beta-glucosidase. Notably, their inhibitory potency against human beta-glucocerebrosidase (GCase) was found to be strongly dependent on the nature of aglycone-type moieties attached at the sulfur atom. In the particular case of omega-substituted hexadecyl chains, an amazing influence of the terminal group was observed. A comparative study on a series of Glc-PSO derivatives suggests that hydrogen bond acceptor functionalities, e.g. fluoro or methyloxycarbonyl, significantly stabilize the Glc-PSO:GCase complex. The S-(16-fluorohexadecyl)-PSO glycomimetic turned out to be a more potent GCase competitive inhibitor than ambroxol, a non glycomimetic drug currently in pilot trials as a pharmacological chaperone for Gaucher disease. Moreover, the inhibition constant increased by one order of magnitude when shifting from neutral (pH 7) to acidic (pH 5) media, a favorable characteristic for a chaperone candidate. Indeed, the fluoro-PSO derivative also proved superior to ambroxol in mutant GCase activity enhancement assays in N370S/N370S Gaucher fibroblasts. The results presented here represent a proof of concept of the potential of exploiting long-range non-glycone interactions for the optimization of glycosidase inhibitors with chaperone activity. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.11.002

文献信息

• Synthesis and Antibacterial Evaluation of Bis‐thiazolium, Bis‐imidazolium, and Bis‐triazolium Derivatives
  作者：Benoît Thomas、Raphaël E. Duval、Stéphane Fontanay、Mihayl Varbanov、Michel Boisbrun

  DOI：10.1002/cmdc.201900151

  日期：2019.7.3

  compounds: bis‐thiazoliums, bis‐imidazoliums, and bis‐1,2,4‐triazoliums. If some compounds of the first series showed fair antibacterial activity, most of those belonging to the two other series were highly potent, with minimum inhibitory concentrations close to 1 μg mL−1. Some of them also exhibited low toxicity toward eukaryotic MRC‐5 lung fibroblasts, and we showed that this toxicity is clearly correlated

  鉴于细菌耐药性在世界范围内的传播，迫切需要开发具有有效抗菌活性且不受该现象影响的新化合物。季铵化合物已被用作消毒剂多年，但是最近的进展表明，与通常使用的单阳离子化合物相比，聚阳离子衍生物具有更强的活性，并且不易产生细菌耐药性。从这个意义上讲，我们制备了三套新的双阳离子化合物：双噻唑鎓，双咪唑鎓和双1,2,4-三唑鎓。如果第一个系列的某些化合物显示出良好的抗菌活性，则其他两个系列的大多数化合物都具有很高的效力，最低抑菌浓度接近1μgmL -1。它们中的一些对真核MRC-5肺成纤维细胞的毒性也很低，我们证明了这种毒性与Clog P明显相关。最后，发现四种选定的化合物表现出明显的杀菌作用。
• Unexpected Regiochemistry in the Benzannulation Reaction of Fischer Carbene Complexes in the Synthesis of Cyclophanes
  作者：Huan Wang、William D. Wulff、Arnold L. Rheingold

  DOI：10.1021/ja0020106

  日期：2000.10.1

  complex 6 would undergo an intramolecular benzannulation with incorporation of the tethered terminal alkyne to givem-cyclophane8b in 58% yield.4,5 This method gives synthetically useful yields of m-cyclophanes and has been examined for tether lengths up to 17 methylenes with no dropoff in yield (60% yield forn ) 17). Them-cyclophane8b was expected from this reaction on the basis of the regiochemistry observed

  Fischer 卡宾配合物与炔烃的苯环化反应是构建取代苯酚的最通用方法之一。1 之前观察到的两种可能的区域化学结果在 4-甲氧基苯酚 2a 和 2b 中进行了说明，它们在炔烃的结合方向上有所不同。炔烃结合的区域化学通常由炔烃 2,3 的两个取代基之间的空间差异控制，并且最大的取代基优先引入与苯酚官能团相邻，如 2a 所示。整个过程的断开显示在 3 中三个亚基的组装中。我们在这里报告了苯酚 4 的观察结果，该反应的新区域异构体是出乎意料的，因为它的形成需要破坏卡宾 - 碳和复合物中含碳取代基 R 1 之间的碳 - 碳键。苯酚4形成过程中的整体组装如图5所示，其中起始卡宾配合物的乙烯基以与正常苯酚2a和2b相反的方式结合。我们最近报道，β-系链乙烯基铬卡宾配合物6将经历一种分子内苯并环化，将连接的末端炔烃以 58% 的产率加入到环芳烃 8b 中。4,5 这种方法可提供间环芳烃的合成有用产率，并且已经检查了长达
• Quaternary bis-ammonium salt precursors and their uses as prodrugs having an antiparasitic activity
  申请人：Vial Henri

  公开号：US06972343B1

  公开（公告）日：2005-12-06

  The invention concerns drug precursors with antimalarial effect, characterised in that it consists in quaternary bis-ammonium salts of general formula (I) wherein A and A′, identical or different, are respectively either a group A1 and A′1 of formula (1) wherein n=2 to 4; R′1 is hydrogen, C1-C5 alkyl, optionally substituted by an aryl, a hydroxy, an alkoxy, wherein the alkyl comprises 1 to 5 C, or aryloxy and W is halogen or a nucleofuge group; or a group A2 which represents formyl-CHO, or acetyl-COCH3. B and B′, identical or different, represent respectively either the group B1 and B′1, if A and A′ respectively represent A1, A′1, B1, B′1 representing a group R1 which has the same definition as R′1 above, but cannot be a hydrogen atom; or respectively the groups B2 and B′2, if A and A′ represent A2, B2 or B′2 being the group R1 as defined above, or a group of formula (2) wherein —Ra is RS— or RCO—, wherein R is a C1-C6 alkyl, substituted if required, a phenyl or benzyl, wherein the phenyl is substituted if required, the latter being optionally substituted; R2 is hydrogen, C1-C5 alkyl, or a —CH2-COO— (C1-C5)alkyl group; and R3 is hydrogen, C1-C5 alkyl or alkenyl, substituted if required, a phosphate, an alkoxy wherein the alkyl is a C1-C3 alkyl, or aryloxy; or an alkyl (or arylcarbonyloxy; or R2 and R3 form together a cycle with 5 or 6 C; R and R3 can be bound to form a cycle. ± represents: either a single bond when A and A′ represent A1 and A′1: or when A and A′ represent A2, and B2 and B′2 Represent (3) either, when A and A′ are —CHO or —COCH3 and B2 and B′2 are R1, a group of formula (4) or a group of formula (5) wherein (a) represents a bond towards Z and (b) a bond towards the nitrogen atom. Z is a C9-C21 alkyl, if required with insertion of one or several bonds, and/or one or several heteroatoms O and/or S and/or several aromatic cycles, and the pharmaceutically acceptable salts of said compounds. Said precursors and cyclized thiazolium derivatives are useful as antiparasitic medicines in particular antimalarial and antibabesiosis.

  该发明涉及具有抗疟疾作用的药物前体，其特征在于它由通式(I)的季铵双盐组成，其中A和A′，相同或不同，分别是通式(1)的A1和A′1基团，其中n=2至4；R′1是氢，C1-C5烷基，可选地被芳基、羟基、烷氧基（其中烷基包括1至5个碳）、芳氧基取代，W是卤素或亲核离去基；或者是代表甲酰基-CHO或乙酰基-COCH3的A2基团。B和B′，相同或不同，分别代表A和A′分别表示A1、A′1、B1、B′1的情况下的B1和B′1基团，其中B1、B′1代表与上述R′1相同定义的R1基团，但不能是氢原子；或者分别代表A和A′表示A2的情况下的B2和B′2基团，其中B2或B′2是如上定义的R1基团，或者是通式(2)的基团，其中-Ra是RS-或RCO-，其中R是C1-C6烷基，必要时取代，苯基或苄基，其中苯基在必要时取代，后者是可选地取代的；R2是氢、C1-C5烷基，或者是—CH2-COO-(C1-C5)烷基；R3是氢、C1-C5烷基或烯烃基，必要时取代，磷酸酯、烷氧基（其中烷基是C1-C3烷基）或芳氧基；或者是烷基（或芳基羰基氧基；或者R2和R3共同形成一个含有5或6个碳的环；R和R3可以结合形成一个环。±表示：当A和A′表示A1和A′1时，是单键；或者当A和A′表示A2，B2和B′2表示(3)时，当A和A′为—CHO或—COCH3，B2和B′2为R1时，是通式(4)的基团或通式(5)的基团，其中(a)表示朝向Z的键，(b)表示朝向氮原子的键。Z是C9-C21烷基，必要时插入一个或多个键，和/或一个或多个杂原子O和/或S，和/或几个芳香环，以及所述化合物的药学上可接受的盐。所述前体和环化噻唑衍生物作为抗寄生虫药物，特别是抗疟疾和抗巴贝斯病的药物是有用的。
• The First Examples of a <i>Meta</i>-Benzannulation from the Reaction of Fischer Carbene Complexes with Alkynes
  作者：Huan Wang、Jie Huang、William D. Wulff、Arnold L. Rheingold

  DOI：10.1021/ja035428n

  日期：2003.7.1

  intramolecular benzannulations of carbene complexes with alkynes are examined where the alkyne is tethered to the alpha-carbon of the vinyl carbene complex. These reactions are sensitive to the length of the tether and to the nature of the solvent. With a tether length of 16 methylenes, the reaction occurs in the same fashion as the intermolecular reactions to give a p-cyclophane. With intermediate

  检查卡宾配合物与炔烃的分子内苯环化，其中炔烃系在乙烯基卡宾配合物的α-碳上。这些反应对系绳的长度和溶剂的性质很敏感。系链长度为 16 亚甲基时，反应以与分子间反应相同的方式发生，得到对环烷。对于中间系链长度 (n = 10, 13)，该反应产生了一个额外的对环芳，其中两个氧取代基在芳烃环上是间位的。这种类型的产品是前所未有的卡宾配合物和炔烃的反应，并且非常令人惊讶，因为这种产品的形成需要乙烯基卡宾配合物的 α-和β-碳之间的碳-碳键被破坏。
• [EN] NEW LIGANDS FOR TARGETING OF S1P RECEPTORS FOR IN VIVO IMAGING AND TREATMENT OF DISEASES<br/>[FR] NOUVEAUX LIGANDS POUR LE CIBLAGE DE RÉCEPTEURS DE S1P, UTILISÉS DANS L'IMAGERIE IN VIVO ET LE TRAITEMENT DE MALADIES
  申请人：UNIV MUENSTER WILHELMS

  公开号：WO2013026765A1

  公开（公告）日：2013-02-28

  The present invention relates to novel compounds of formulae (I) and (II) which are useful in the prevention, treatment and diagnosis, in vivo diagnosis of diseases or disorders related to S1P receptors, in particular, in diseases which are connected to the regulatory function of sphingosine-1-phosphate (S1P) and its analogues, such as inflammation, pain, autoimmune diseases and cardiovascular diseases.

  本发明涉及具有以下式（I）和（II）的新化合物，其在与S1P受体相关的疾病或紊乱的预防、治疗和体内诊断方面具有用途，特别是在与神经酰胺-1-磷酸鞘氨醇（S1P）及其类似物的调节功能相关的疾病中，如炎症、疼痛、自身免疫疾病和心血管疾病。