methyl 6-hydroxy-5-iodo-2-naphthoate | 364372-03-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 6-hydroxy-5-iodo-2-naphthoate
• 英文别名: Methyl 6-hydroxy-5-iodonaphthalene-2-carboxylate
• CAS: 364372-03-2
• 化学式: C₁₂H₉IO₃
• 分子量: 328.106
• InChiKey: RIFGGBOSKMTNDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 6-hydroxy-5-iodo-2-naphthoate 在 吡啶 、 4-二甲氨基吡啶 、 S-联萘酚磷酸酯 、 potassium carbonate 、 (4R,5R)-2-(diisopropylamino)-1,3-dimethyl-4,5-diphenyl-1,3,2-diazaphospholidine 2-selenide 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 38.0h， 生成 methyl 2-hydroxy-2'-((2-nitrophenyl)selanyl)-3',4'-dihydro-[1,1'-binaphthalene]-6-carboxylate
  参考文献：
  名称：

  路易斯碱催化炔烃的硒基官能化，具有酸控制的发散化学选择性†

  摘要：

  首次开发了路易斯碱催化和布朗斯台德酸控制的炔烃化学发散亲电硒基官能化。各种含硒四取代烯烃很容易以中等至优异的产率获得，并且具有完全的 E/Z 选择性。以1-乙炔基萘酚衍生物为底物，在不存在酸添加剂的情况下，通过分子间氧亲核攻击生成直链含硒四取代烯烃；相比之下，环状含硒四取代烯烃是通过添加布朗斯台德酸进行分子内碳亲核捕获而生成的。

  DOI：

  10.1002/cjoc.202400015
• 作为产物：
  描述：

  2-溴-6-甲氧基萘 在 sodium hydroxide 、 一氯化碘 、 三溴化硼 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 methyl 6-hydroxy-5-iodo-2-naphthoate
  参考文献：
  名称：

  Utilization of a Peptide Lead for the Discovery of a Novel PTP1B-Binding Motif

  摘要：

  Examination of the PTP1B inhibitory potency of an extensive series of phosphotyrosyl (pTyr) mimetics (Xxx) expressed in the EGFr-derived hexapeptide platform Ac-Asp-Ala-Asp-Xxx-Leu-amide previously led to the finding of high inhibitory potency when Xxx = 4-(phosphono-difluoromethyl)phenylalanyl (F(2)Pmp) (K-i = 0.2 muM) and when Xxx = 3-carboxy-4-carboxy-methyloxyphenylalanyl (K-i = 3.6 muM). In the first instance, further work led from the F(2)Pmp-containing peptide to monomeric inhibitor, 6-(phosphonodifluoromethyl)-2-naphthoic acid (Ki = 22 muM), and to the pseudo-dipeptide mimetic, N-[6-(phosphonodifluoromethyl)-2-naphthoyl]-glutamic acid (K-i = 12 muM). In the current study, a similar approach was applied to the 3-carboxy-4-carboxymethyloxyphenylalanyl-containing peptide, which led to the preparation of monomeric 5-carboxy-6-carboxymethyloxy-2-naphthoic acid (K-i = 900 muM). However, contrary to expectations based on the aforementioned F(2)Pmp work, incorporation of this putative pTyr mimetic into the pseudo-dipeptide, N-[5-carboxy-6-carboxymethyloxy-2-naphthoyl]-glutamic acid, resulted in a substantial loss of binding affinity. A reevaluation of binding orientation for 5-carboxy-6-carboxymethyloxy-2-naphthoic acid was therefore undertaken, which indicated a 180 degrees reversal of the binding orientation within the PTP1B catalytic site. In the new orientation, the naphthyl 2-carboxyl group, and not the o-carboxy carboxymethyloxy groups, mimics a phosphoryl group. Indeed, when 5-carboxy-2-naphthoic acid itself was examined at neutral pH for inhibitory potency, it was found to have K-i = 31 +/- 7 muM, which is lower than parent 5-carboxy-6-carboxymethyloxy-2-naphthoic acid. In this fashion, 5-carboxy-2-naphthoic acid (or more appropriately, 6-carboxy-1-naphthoic acid) has been identified as a novel PTP1B binding motif.

  DOI：

  10.1021/jm010020r

文献信息

• Asymmetric Hydrophosphinylation of Alkynes: Facile Access to Axially Chiral Styrene‐Phosphines
  作者：Baohua Cai、Yuan Cui、Jian Zhou、Yong‐Bin Wang、Limin Yang、Bin Tan、Jun (Joelle) Wang

  DOI：10.1002/anie.202215820

  日期：2023.1.16

  Through a newly developed Cu/CPA co-catalytic system, the direct hydrophosphinylation of alkynes with nucleophilic phosphine oxides was achieved to access novel axially chiral phosphorus-containing alkenes in high yields and excellent enantioselectivities (up to 99 % yield and 99 % ee). DFT calculations were performed to elucidate the reaction pathway and the enantiocontrol model.

  通过新开发的 Cu/CPA 助催化系统，实现了炔烃与亲核氧化膦的直接氢化膦酰化，以高产率和优异的对映选择性（高达 99% 产率和 99% ee）获得新型轴向手性含磷烯烃。进行 DFT 计算以阐明反应途径和对映体控制模型。
• Copper-Catalyzed Asymmetric Functionalization of Vinyl Radicals for the Access to Vinylarene Atropisomers
  作者：Liang Fu、Xin Chen、Wenzheng Fan、Pinhong Chen、Guosheng Liu

  DOI：10.1021/jacs.3c04498

  日期：2023.6.21

  A novel asymmetric radical strategy for the straightforward synthesis of atropisomerically chiral vinyl arenes has been established herein, proceeding through copper-catalyzed atroposelective cyanation/azidation of aryl-substituted vinyl radicals. Critical to the success of the radical relay process is the atroposelective capture of the highly reactive vinyl radicals with chiral L*Cu(II) cyanide or

  本文建立了一种用于直接合成阻转异构手性乙烯基芳烃的新颖的不对称自由基策略，通过芳基取代的乙烯基自由基的铜催化的阻转选择性氰化/叠氮化进行。自由基中继过程成功的关键是用手性 L*Cu(II) 氰化物或叠氮化物对高反应性乙烯基自由基进行间质选择性捕获。此外，这些轴向手性乙烯基芳烃产物可以通过轴到中心手性转移过程轻松转化为阻转异构体富集的酰胺和胺、对映体富集的苄基腈，以及用于化学、非对映和对映选择性的阻转异构纯有机催化剂（4 + 2) 环化反应。