(3-Iodo-5-methoxy-4-methoxymethoxy-phenyl)-methanol | 368435-39-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3-Iodo-5-methoxy-4-methoxymethoxy-phenyl)-methanol
• 英文别名: [3-iodo-5-methoxy-4-(methoxymethoxy)phenyl]methanol
• CAS: 368435-39-6
• 化学式: C₁₀H₁₃IO₄
• 分子量: 324.115
• InChiKey: JSSPHVODMFPDGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 重原子数：
  15.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3-Iodo-5-methoxy-4-methoxymethoxy-phenyl)-methanol 在 二苯基磷酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 生成 3-Iodo-5-methoxy-4-methoxymethoxy-benzylamine
  参考文献：
  名称：

  Halogenation of 4-hydroxy-3-methoxybenzyl thiourea TRPV1 agonists showed enhanced antagonism to capsaicin

  摘要：

  Selected potent TRPV1 agonists (1-6) have been modified by 5- or 6-halogenation on the aromatic A-region to analyze their effects on potency and efficacy (agonism versus antagonism). The halogenation caused enhanced functional antagonism at TRPV1 compared to the corresponding prototype agonists. The analysis of SAR indicated that the antagonism was enhanced as the size of the halogen increased (I > Br > CI) and when the 6-position was halogenated. Compounds 23c and 31b were found to be potent full antagonists with K-i (as functional antagonist) = 23.1 and 30.3 nM in rTRPV1/CHO system, respectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.059
• 作为产物：
  描述：

  3-iodo-5-methoxy-4-methoxymethoxy-benzaldehyde 在 sodium tetrahydroborate 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 (3-Iodo-5-methoxy-4-methoxymethoxy-phenyl)-methanol
  参考文献：
  名称：

  Halogenation of 4-hydroxy-3-methoxybenzyl thiourea TRPV1 agonists showed enhanced antagonism to capsaicin

  摘要：

  Selected potent TRPV1 agonists (1-6) have been modified by 5- or 6-halogenation on the aromatic A-region to analyze their effects on potency and efficacy (agonism versus antagonism). The halogenation caused enhanced functional antagonism at TRPV1 compared to the corresponding prototype agonists. The analysis of SAR indicated that the antagonism was enhanced as the size of the halogen increased (I > Br > CI) and when the 6-position was halogenated. Compounds 23c and 31b were found to be potent full antagonists with K-i (as functional antagonist) = 23.1 and 30.3 nM in rTRPV1/CHO system, respectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.059

文献信息

• Enantioselective Ruthenium-Catalyzed Benzocyclobutenone–Ketol Cycloaddition: Merging C–C Bond Activation and Transfer Hydrogenative Coupling for Type II Polyketide Construction
  作者：Brett R. Ambler、Ben W. H. Turnbull、Sankar Rao Suravarapu、Maulen M. Uteuliyev、Nancy O. Huynh、Michael J. Krische

  DOI：10.1021/jacs.8b05724

  日期：2018.7.25

  The first enantioselective intermolecular metal-catalyzed cycloadditions of benzocyclobutenones via C-C bond oxidative addition are described. In the presence of a ruthenium(0) complex modified by ( R)-DM-SEGPHOS, tetralone-derived ketols and benzocyclobutenones combine to form cycloadducts with complete regio- and diastereoselectivity and high enantioselectivity. Using this method, the "bay region"

  描述了苯并环丁烯酮通过 CC 键氧化加成的第一个对映选择性分子间金属催化环加成。在 (R)-DM-SEGPHOS 修饰的钌 (0) 络合物存在下，四氢萘酮衍生的酮醇和苯并环丁烯酮结合形成具有完全区域和非对映选择性以及高对映选择性的环加合物。利用该方法制备了安古环素天然产物沙霉素的“湾区”亚结构。