5-(iodomethyl)-1,2,3-trimethoxybenzene | 18111-18-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(iodomethyl)-1,2,3-trimethoxybenzene
• 英文别名: 3,4,5-trimethoxybenzyl iodide；5-iodomethyl-1,2,3-trimethoxy-benzene；5-Jodmethyl-1,2,3-trimethoxy-benzol
• CAS: 18111-18-7
• 化学式: C₁₀H₁₃IO₃
• 分子量: 308.116
• InChiKey: MRBLMQBDPAINQJ-UHFFFAOYSA-N

物化性质

• 熔点：
  57-58 °C (decomp)
• 沸点：
  327.8±42.0 °C(Predicted)
• 密度：
  1.567±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(iodomethyl)-1,2,3-trimethoxybenzene 在 四氯化钛 、 双(三甲基硅烷基)氨基钾 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 (R)-3-Hydroxymethyl-6,7,8-trimethoxy-2-((R)-2-methoxy-1-phenyl-ethyl)-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid
  参考文献：
  名称：

  Asymmetric synthesis of quaternary tetrahydroisoquinoline-3-carboxylic acid derivatives

  摘要：

  A new route towards the asymmetric preparation of quaternary 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid derivatives has been developed. The key step involves an intramolecular Pictet-Spengler reaction of an oxazolidino ester. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00075-2
• 作为产物：
  描述：

  3,4,5-三甲氧基苄氯 在 sodium iodide 作用下， 反应 14.0h， 以90%的产率得到5-(iodomethyl)-1,2,3-trimethoxybenzene
  参考文献：
  名称：

  6,7-二甲氧基-2-苯乙基-1,2,3,4-四氢异喹啉衍生物作为多药耐药逆转剂的结构-活性关系研究。

  摘要：

  为了研究两种P-糖蛋白（P-gp）调节剂elacridar和tariquidar的结构-活性关系，合成并研究了一系列衍生物。然后，插入不同的芳基取代的酰胺，并探讨改变酰胺功能的影响，合成了相应的等位酯衍生物和一些烷基胺类似物。对新化合物进行了研究，以评估其与其他两种ABC转运蛋白（多药耐药相关蛋白1（MRP-1）和乳腺癌耐药蛋白（BCRP））的P-gp相互作用谱和选择性。对酰胺和酯衍生物对自发或酶促水解的化学稳定性的研究表明，这些化合物在磷酸盐缓冲液和人体血浆中稳定。这项研究使我们能够评估在三个外排泵上三个系列的选择性，并提出定义P-gp相互作用曲线的结构要求。我们确定了两种P-gp底物，一种P-gp抑制剂和三种对BCRP具有活性的酯衍生物，这为开发对该泵具有活性的配体开辟了新的前景。

  DOI：

  10.1002/cmdc.201700239

文献信息

• 5-amino-4-hydroxyhexanoic acid derivatives
  申请人：Ciba-Geigy Corporation

  公开号：US05643878A1

  公开（公告）日：1997-07-01

  Compounds of formula I ##STR1## or their hydroxy-protected derivatives, and compounds of formula I' ##STR2## wherein T is an acyl radical of formula Z ##STR3## wherein R.sup.z is unsubstituted or substituted hydrocarbyl wherein at least one carbon atom has been replaced by a hetero atom with the proviso that a hetero atom is not bonded directly to the carbonyl to which the radical R.sup.z is bonded, alkyl having two or more carbon atoms, lower alkenyl, lower alkynyl, aryl or unsubstituted or substituted amino, and wherein the radicals R.sub.1, B.sub.1, R.sub.2, R.sub.3, A.sub.1, A.sub.2 and NR.sub.4 R.sub.5 are as defined in the description, and precursors thereof, are described. The compounds have pharmaceutical activity, for example in the treatment of retroviral diseases, such as AIDS.

  公式I的化合物##STR1##或其羟基保护衍生物，以及公式I'的化合物##STR2##，其中T是公式Z的酰基自由基##STR3##，其中R.sup.z是不取代或取代的碳氢化合物，至少有一个碳原子被杂原子替换，但需满足杂原子不直接与R.sup.z连接的酰基相连，烷基含有两个或更多碳原子，低级烯基，低级炔基，芳基或不取代或取代的氨基，且其中R.sub.1、B.sub.1、R.sub.2、R.sub.3、A.sub.1、A.sub.2和NR.sub.4 R.sub.5如描述中定义，以及它们的先驱物，都有药物活性，例如在治疗反转录病毒疾病，如艾滋病。
• A simplified isoquinoline synthesis
  作者：Dale L. Boger、Christine E. Brotherton、Marshall D. Kelley

  DOI：10.1016/s0040-4020(01)93272-7

  日期：——

  A simple variation of the Pomeranz-Fritsch cyclization provides a short, efficient route to isoquinolines. Treatment of benzylic halides or mesylates 1 with the sodium anion of N-tosyl aminoacetaldehyde dimethyl acetal (2) followed by acid-catalyzed cyclization provides an effective, two-step preparation of isoquinolines 4.

  Pomeranz-Fritsch环化的简单变化为异喹啉提供了一条短而有效的途径。用N-甲苯磺酰基氨基乙醛二甲基乙缩醛的钠阴离子处理苄基卤化物或甲磺酸盐1（2），然后进行酸催化环化，可有效地进行两步制备异喹啉4。
• Enantio- and Diastereoselective Assembly of Tetrahydrofuran and Tetrahydropyran Skeletons with All-Carbon-Substituted Quaternary Stereocenters
  作者：Zhilong Chen、Jianwei Sun

  DOI：10.1002/anie.201306801

  日期：2013.12.16

  desymmetrization of meso 1,3‐diols through mono‐transacetalization with a tethered acetal unit (see scheme). This new strategy leads to the efficient assembly of tetrahydrofuran and tetrahydropyran skeletons bearing remote all‐carbon‐substituted quaternary stereocenters that are not straightforward to access by other methods.

  手性磷酸（HB *）通过束缚乙缩醛单元的单反缩醛化催化中消旋1,3-二醇的不对称脱对称反应（参见方案）。这项新策略可有效组装带有远程全碳取代的季立体中心的四氢呋喃和四氢吡喃骨架，而其他方法无法直接访问这些骨架。
• [EN] COMPOUNDS AND KITS FOR PREPARING IMAGING AGENTS AND METHODS OF IMAGING<br/>[FR] COMPOSES ET KITS DE PREPARATION D'AGENTS D'IMAGERIE ET PROCEDES D'IMAGERIE
  申请人：GEN ELECTRIC

  公开号：WO2005023317A1

  公开（公告）日：2005-03-17

  Compounds that include a targeting moiety bound to a regioselective leaving group are useful for preparing imaging agents. The imaging agents can be isolated from by­products derived from the leaving group based on differences in the chemical attributes (e.g., net charge or polarity) of the molecules or physical attributes of the molecules through the use of a solid support. Methods of producing an imaging agent include the steps of providing a compound that includes a targeting moiety bound to a support via a linker group that contains a site for regioselective substitution of a detectable species, contacting the compound with a solution containing the detectable species, and recovering the imaging agent. Kits which include a first container (5) having therein a solution (31) containing a detectable species and a second container (2) having therein a compound that includes a targeting moiety bound to a support (30) via a leaving group that contains a site for regioselective substitution of the detectable species are also useful for preparing imaging agents.

  将包括与一个区域选择性离去基团结合的靶向基团的化合物用于制备成像剂是有用的。这些成像剂可以通过固体支持物来分离出来，基于分子的化学属性（例如净电荷或极性）或物理属性之间的差异，以此与离去基团衍生的副产物进行区分。制备成像剂的方法包括以下步骤：提供一个包含通过链连接基团与支持物相结合的靶向基团的化合物，该链连接基团包含一个用于区域选择性取代可检测物种的位点；将该化合物与含有可检测物种的溶液接触；并回收成像剂。还有一种用于制备成像剂的工具包，其中包括一个第一容器（5），其中含有一个含有可检测物种的溶液（31），以及一个第二容器（2），其中含有一个通过含有一个用于区域选择性取代可检测物种的离去基团的位点而与支持物（30）相结合的靶向基团的化合物。
• Antiviral ethers of aspartate protease substrate isosteres
  申请人：Ciba-Geigy Corporation

  公开号：US05663200A1

  公开（公告）日：1997-09-02

  Antiretroviral compounds (which are effective, for example, against HIV) of the formula I ##STR1## in which R.sub.1 is an acyl radical lower-alkoxyl-lower-alkanoyl whose lower alkoxy radical is unsubstituted or is substituted by halogen, phenyl, lower alkoxy or a heterocyclic radical selected from piperidinyl, pyrrolidinyl, tetrahydropyranyl, tetrahydrofuranyl, thiazolidinyl, thiazolyl, indolyl or 4H-1-benzopyranyl which is unsubstituted or substituted by oxo, hydroxyl, amine, lower alkyl, lower-alkoxycarbonyl and/or phenyl-lower-alkoxycarbonyl; lower alkanoyl which is unsubstituted or is substituted by one of the said unsubstituted or substituted heterocyclic radicals; arylcarbonyl or heterocyclylcarbonyl which are substituted by heterocyclyl or heterocyclyl-lower-alkyl; phenyl-lower-alkanoyl which is substituted by hydroxyl and lower alkyl; or arylsulfonyl; or the residue of an amino acid which is defined in accordance with the description (and which may be acylated on the amino nitrogen by one of the abovementioned acyl radicals); R.sub.2 and R.sub.3 are in each case cyclohexyl, cyclohexenyl, phenyl, naphthyl or tetrahydronaphthyl which are unsubstituted or substituted by lower alkyl, phenyl, cyanophenyl, phenyl-lower-alkyl, halogen, halo-lower-alkyl, cyano, hydroxyl, lower alkoxy, phenyl-lower-alkoxyl, pyridyl-lower-alkoxy, lower-alkoxy-lower-alkoxy, lower-alkoxycarbonyl-lower-alkoxy, carboxyl-lower-alkoxy, hydroxyl-lower-alkoxy, carbamoyl-lower-alkoxy, cyano-lower-alkoxy, and phenyl-lower-alkanesulfonyl which is unsubstituted or substituted by halogen; R.sub.4 is lower alkyl, cyclohexyl or phenyl; and R.sub.5 is lower alkyl; and n is 1 or 2, or salts thereof, are novel.

  式I中的抗逆转录病毒化合物（例如针对HIV有效）## STR1 ##其中R.sub.1是酰基较低的烷氧基较低的酰基，其较低的烷氧基未取代或被卤素，苯基，较低的烷氧基或从哌啶基，吡咯烷基，四氢吡喃基，四氢呋喃基，噻唑烷基，噻唑基，吲哚基或未取代或取代为氧代，羟基，氨基，较低的烷基，较低的烷氧羰基和/或苯基-较低的烷氧羰基选择的杂环基团取代；未取代或取代为上述未取代或取代的杂环基团之一的未取代或取代的较低烷酰基；被杂环基或杂环基较低烷基取代的苯基羰基或杂环基羰基；被羟基和较低烷基取代的苯基较低烷酰基；或苯基磺酰基；或根据描述定义的氨基酸残基（并且可以通过上述酰基之一在氨基氮上酰化）；R.sub.2和R.sub.3分别是未取代或取代的环己基，环己烯基，苯基，萘基或四氢萘基，其未取代或被较低烷基，苯基，氰基苯基-较低烷基，卤素，卤代较低烷基，氰基，羟基，较低烷氧基，苯基-较低烷氧基，吡啶基-较低烷氧基，较低烷氧基-较低烷氧基，较低烷氧基羰基-较低烷氧基，羧基-较低烷氧基，羟基-较低烷氧基，氨基甲酰-较低烷氧基，氰基-较低烷氧基和未取代或取代为卤素的苯基-较低烷基磺酰基；R.sub.4是较低的烷基，环己基或苯基；而R.sub.5是较低的烷基；n为1或2，或其盐，是新颖的。