2-(3-adamantan-1-yl-4-methoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane | 1036766-56-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(3-adamantan-1-yl-4-methoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane
• 英文别名: 1,3,2-dioxaborolane, 2-(4-methoxy-3-tricyclo[3.3.1.13,7]dec-1-ylphenyl)-4,4,5,5-tetramethyl；3-(1-adamantyl)-4-methoxyphenylboronic acid pinacol ester；3-(1-adamantyl)-4-methoxyphenylboric acid pinacol ester；2-[3-(1-adamantyl)-4-methoxyphenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 1036766-56-9
• 化学式: C₂₃H₃₃BO₃
• 分子量: 368.324
• InChiKey: MZZSSQYTKSTPQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.46
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.74
• 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：

  2-(3-adamantan-1-yl-4-methoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 在 sodium chlorite 、 disodium hydrogenphosphate 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 2-甲基-2-丁烯 、 草酰氯 、 lithium hydroxide monohydrate 、 sodium carbonate 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 82.0h， 生成 3-(3′-adamantan-1-yl-2-carbamoyl-4′-methoxybiphenyl-4-yl)acrylic acid
  参考文献：
  名称：

  Novel adamantyl retinoid-related molecules with POLA1 inhibitory activity

  摘要：

  Atypical retinoids (AR) or retinoid-related molecules (RRMs) represent a promising class of antitumor compounds. Among AR, E-3-(3'-adamantan-1-yl-4'-hydroxybiphenyl-4-yl)acrylic acid (adarotene), has been extensively investigated. In the present work we report the results of our efforts to develop new adarotene-related atypical retinoids endowed also with POLA1 inhibitory activity. The effects of the synthesized compounds on cell growth were determined on a panel of human and hematological cancer cell lines. The most promising compounds showed antitumor activity against several tumor histotypes and increased cytotoxic activity against an adarotene-resistant cell line, compared to the parent molecule. The antitumor activity of a selected compound was evaluated on HT-29 human colon carcinoma and human mesothelioma (MM487) xenografts. Particularly significant was the in vivo activity of the compound as a single agent compared to adarotene and cisplatin, against pleural mesothelioma MM487. No reduction of mice body weight was observed, thus suggesting a higher tolerability with respect to the parent compound adarotene.

  DOI：

  10.1016/j.bioorg.2020.104253
• 作为产物：
  描述：

  2-(1-金刚烷基)-4-溴苯甲醚 在 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 生成 2-(3-adamantan-1-yl-4-methoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane
  参考文献：
  名称：

  平行宇宙之门：生物表面活性剂在胶束催化中的应用

  摘要：

  胶束催化通过增溶疏水性有机化合物为催化转化提供了一种绿色替代方法。生物表面活性剂代表了合成表面活性剂的可持续替代品，因为它们具有生物降解性、低毒性和可再生原料的生产能力。在这项工作中，我们展示了生物表面活性剂鼠李糖脂在各种胶束交叉偶联中的适用性，并制备了特殊的氟化共轭体系、活性药物成分 (API) 构建块和生物活性化合物。

  DOI：

  10.1039/d3gc00365e

文献信息

• METHOD FOR PREPARATION OF 6-[3(1-ADAMANTYL) -4-METHOXYPHENYL]-2-NAPHTOIC ACID
  申请人：Kalvinsh Ivars

  公开号：US20100076219A1

  公开（公告）日：2010-03-25

  A method for preparation of 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid is disclosed based on “one pot” synthesis approach including a direct synthesis of boronic acid derivative from 2-(1-adamantyl)-4-bromoanisole and cycloboranes with a subsequent Suzuki-Miyaura coupling with 6-halonaphthenoates and basic hydrolysis of the reaction product in ethylene glycol or 1,2-propanediol.

  揭示了一种制备6-[3-(1-戊二醇基)-4-甲氧基苯基]-2-萘甲酸的方法，基于“一锅法”合成方法，包括从2-(1-戊二醇基)-4-溴基苯甲醚和环硼烷直接合成硼酸衍生物，然后与6-卤代萘酸酯进行Suzuki-Miyaura偶联反应，最后在乙二醇或1,2-丙二醇中对反应产物进行碱性水解。
• PROCESS FOR PREPARATION OF 6-[3-(1-ADMANTYL)-4-METHOXYPHENYL]-2-NAPHTOIC ACID.
  申请人：Kalvinsh Ivars

  公开号：US20100160677A1

  公开（公告）日：2010-06-24

  A process for preparation of 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid from 2-(1-adamantyl)-4-bromanisolee is disclosed, based on transformation of 2-(1-adamantyl)-4-bromanisole into a Grignard's reagent by using metallic magnesium, anhydrous lithium chloride and dibromoethane followed by transmetallation with borates to 3-(adamantyl)-4-methoxyphenylboronic acid, which is converted into 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid esters by Suzuki-Miyaura cross-coupling reaction with alkyl-6-halonaftoates catalyzed by Pd [0] or Pd/phosphine ligands and followed by basic hydrolysis in ethylene glycol or 1,2-propanediol of ester thus obtained into 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid.

  揭示了一种从2-(1-金刚烷基)-4-溴苯甲醚制备6-[3-(1-金刚烷基)-4-甲氧基苯基]-2-萘甲酸的方法，基于将2-(1-金刚烷基)-4-溴苯甲醚转化为格氏试剂，使用金属镁、无水氯化锂和二溴乙烷进行转化，随后通过与硼酸盐的转金属化反应得到3-(金刚烷基)-4-甲氧基苯基硼酸，再通过Suzuki-Miyaura交叉偶联反应与Pd [0]或Pd/膦配体催化的烷基-6-卤代萘酸酯反应，最后在乙二醇或1,2-丙二醇中进行酯的碱性水解，得到6-[3-(1-金刚烷基)-4-甲氧基苯基]-2-萘甲酸。
• One-pot synthesis of methyl 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthenoate
  作者：V. G. Tribulovich、A. V. Garabadzhiu、I. Kalvins

  DOI：10.1134/s1070363210040328

  日期：2010.4

  leaving group. An alternative method of introducing this functional group is catalytic coupling of boron-containing nucleophilic agent with electrophilic aryl substrate, which unlike the transmetallation reaction can be performed in one stage [2]. The main advantage of direct catalytic heterofunctionalization of aryl halides is its easy technological application. Conditions of this reaction differ only slightly

  6-[3(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid (Adapalene) 分子构建骨架的关键阶段是 3-(1-adamantyl)-4 之间形成 C-C 键-甲氧基苯基和 2carbomethoxy-6-naphthyl 片段。根据 Suzuki-Miyaura [1] 的方法，已知最有效的现代 C-C 键形成方法之一是催化偶联过程。要使用此方法，其中一个偶联片段应带有含硼官能团。为了引入这样的基团，最广泛使用的方法是在具有卤素或烷氧基残基作为离去基团的硼化合物的作用下，预先制备的格氏试剂或锂衍生物的金属转移。引入该官能团的另一种方法是含硼亲核试剂与亲电子芳基底物的催化偶联，与金属转移反应不同，该反应可以在一个阶段进行 [2]。芳基卤化物直接催化异功能化的主要优点是其易于技术应用。该反应的条件与 Suzuki-Miyaura 交叉偶联反
• Synthesis of 3-(1-adamantyl)-4-methoxyphenylboric acid
  作者：V. G. Tribulovich、A. V. Garabadzhiu、I. Kalvins

  DOI：10.1134/s1070363210040316

  日期：2010.4