3-羟基苄基碘 | 102998-68-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-羟基苄基碘
• 英文名称: 3-hydroxybenzyl iodide
• 英文别名: 3-(Iodomethyl)phenol
• CAS: 102998-68-5
• 化学式: C₇H₇IO
• 分子量: 234.036
• InChiKey: ZPHASNOMPKOXET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-羟基苄基碘 在 indium 、 水 作用下， 反应 5.0h， 以86%的产率得到间甲酚
  参考文献：
  名称：

  Indium as a reducing agent. Chemoselective reduction of α-halocarbonyl compounds and benzyl halides by indium metal in water under sonication

  摘要：

  在水中的铟金属在超声波作用下能够高效地将α-卤代羰基化合物和苄基碘还原为相应的去卤化产物，虽然简单烷基和芳基碘在这些条件下保持惰性。

  DOI：

  10.1039/a901493d
• 作为产物：
  描述：

  3-羟基苯甲醇 在 三氟化硼乙醚 、 potassium iodide 作用下， 以 1,4-二氧六环 为溶剂， 生成 3-羟基苄基碘
  参考文献：
  名称：

  Inhibition of Nucleoside Transport by New Analogues of 4-Nitrobenzylthioinosine:  Replacement of the Ribose Moiety by Substituted Benzyl Groups

  摘要：

  4-Nitrobenzylthioinosine (NBTI, 1) is a well-known inhibitor for the nucleoside transport protein ENT1. However, its highly polar nature is unfavorable for oral absorption and/or penetration into the CNS. In the search for compounds with lower polarity than NBTI we replaced its ribose moiety by substituted benzyl groups. Halogen, hydroxyl, (trifluoro)methyl(-oxy), nitro, and amine functionalities were among the substituents at the benzyl group. In general, substitution of the benzyl group resulted in a lower affinity for ENT1. Only 2-hydroxyl substitution showed a higher affinity. Most likely this is the result of hydrogen bonding. Substitution at the 2-position of the benzyl group with aryl groups was also addressed. Compared to parent compound carrying a 2-phenylbenzyl group, all synthesized analogues gave higher affinities. Introduction of fluoro, trifluoromethyl, methoxy, and hydroxyl groups at the phenyl group clearly showed that addition to the 4-position was preferable. Despite the highly different character of a ribose and a benzyl group, K-i values in the low nanomolar range were obtained for the benzyl-substituted derivatives. Compound 35, LUF5919, and compound 60, LUF5929, displayed the highest affinity (K-i = 39 nM for both compounds), having a polar surface area of 101 Angstrom(2) and 85 Angstrom(2), respectively.

  DOI：

  10.1021/jm049735v

文献信息

• [EN] MACROCYCLIC INHIBITORS OF FLAVIVIRIDAE VIRUSES<br/>[FR] INHIBITEURS MACROCYCLIQUES DE VIRUS FLAVIVIRIDAE
  申请人：GILEAD SCIENCES INC

  公开号：WO2012078915A1

  公开（公告）日：2012-06-14

  Provided are compounds of Formula (I): and pharmaceutically acceptable salts and esters thereof. The compounds, compositions, and methods provided are useful for the treatment of Flaviviridae virus infections, particularly hepatitis C infections.

  提供的是化合物的化学式(I)及其药用可接受的盐和酯。所提供的化合物、组合物和方法对于治疗黄病毒科病毒感染，特别是丙型肝炎感染是有用的。
• Reagents and synthetic methods 52. Silane reduction of carbonyl compounds in the presence of iodine
  作者：B. Lecea、J.M. Aizpurua、C. Palomo

  DOI：10.1016/s0040-4020(01)82361-9

  日期：1985.1

  utility of 1,1,3,3-tetramethyldisiloxane (TMDS) reagent under the influence of iodine is described. TMDS reagent in combination with iodine produces alkyl iodides from carbonyl compounds and oxiranes in good to excellent yields. Reduction of quinones into hydroquinones is also described. The mentioned transformations are explained from mechanistic points of view.

  描述了在碘影响下的1,1,3,3-四甲基二硅氧烷（TMDS）试剂的合成效用。TMDS试剂与碘结合可从羰基化合物和环氧乙烷以高至极好的收率生产烷基碘。还描述了将醌还原为对苯二酚。所提到的转换是从机械角度进行解释的。
• Electron-transfer-induced photochemical reactions of (silylallyl)iminium and benzylpyrrolinium salts by dual diradical and diradical cation cyclization pathways
  作者：In Seop Cho、Chung Lan Tu、Patrick S. Mariano

  DOI：10.1021/ja00165a052

  日期：1990.4

  The electron-transfer-induced photocyclization reactions of a series of N- and C-silylmethallyl-substituted iminium and 1-benzyl-1-pyrrolinium salts have been investigated in order to gain information about their mechanistic course and to probe their synthetic potential. The results obtained from these studies demonstrate that diradical cation intermediates formed in these processes can be transformed

  已经研究了一系列 N-和 C-甲硅烷基甲代烯丙基取代的亚胺盐和 1-苄基-1-吡咯啉盐的电子转移诱导的光环化反应，以获得有关其机理过程的信息并探讨其合成潜力。从这些研究中获得的结果表明，在这些过程中形成的双自由基阳离子中间体可以通过两种相互竞争的机制途径转化为产物，包括自由基偶联或烯丙基或苄基电离基团的丢失
• LECEA, B.;AIZPURUA, J. M.;PALOMO, C., TETRAHEDRON, 1985, 41, N 20, 4657-4665
  作者：LECEA, B.、AIZPURUA, J. M.、PALOMO, C.

  DOI：——

  日期：——
• HETEROCYCLIC ASPARTYL PROTEASE INHIBITORS
  申请人：Merck Sharp & Dohme Corp.

  公开号：EP2097387B1

  公开（公告）日：2016-05-04