3-hydroxy-5,7-dimethyladamantane-1-carboxylic acid | 14575-03-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-hydroxy-5,7-dimethyladamantane-1-carboxylic acid
• CAS: 14575-03-2
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: AUHXIJPALFNIHE-UHFFFAOYSA-N

物化性质

• 熔点：
  235-236 °C
• 沸点：
  346.6±25.0 °C(Predicted)
• 密度：
  1.337±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-hydroxy-5,7-dimethyladamantane-1-carboxylic acid 在 sodium tetrahydroborate 、 三氟甲磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 Petroleum ether 为溶剂， 反应 5.0h， 生成 5,7-dimethyl-3-(pentanoyloxy)methyl-1-adamantyl pentanoate
  参考文献：
  名称：

  Synthesis, Physicochemical Properties, and Thermo-Oxidative Stability of Diesters of 5,7-Dimethyl-3-hydroxymethyl-1-adamantanol

  摘要：

  Synthesis of 5,7-dimethyl-3-hydroxymethyl-1-adamantanol with limited conformational mobility and of a series of esters based thereon has been performed. The physicochemical properties and thermo-oxidative stability of synthesized diesters have been studied.

  DOI：

  10.1134/s1070363218080091
• 作为产物：
  描述：

  3,5-二甲基-1-金刚烷醇 在 硫酸 、 硝酸 作用下， 反应 9.0h， 生成 3-hydroxy-5,7-dimethyladamantane-1-carboxylic acid
  参考文献：
  名称：

  Process for producing hydroxy adamantane carboxylic acid compounds

  摘要：

  本发明可以提供一种生产由上述式(2)所代表的羟基脑酮酸化合物的方法，包括(i)将上述式(1)所代表的脑酮化合物与一氧化碳反应，或者与在质量浓度为90%或更高的质子酸溶液中制备的一氧化碳源反应，从而使氧化物基团的羧化作用发生，然后(ii)向反应混合物中加入氧化剂，使桥头C—H键氧化，从而生成羟基基团。

  公开号：

  US09051256B1

文献信息

• One-pot synthesis of cage alcohols
  作者：Yu. N. Klimochkin、A. V. Yudashkin、E. O. Zhilkina、E. A. Ivleva、I. K. Moiseev、Ya. F. Oshis

  DOI：10.1134/s1070428017070028

  日期：2017.7

  An efficient one-pot procedure has been developed for the synthesis of cage alcohols with hydroxy groups in the bridgehead positions. The procedure includes initial nitroxylation with nitric acid or a mixture of nitric acid with acetic acid and subsequent hydrolysis in the presence of urea.

  已经开发出一种有效的一锅法程序，用于合成在桥头位置具有羟基的笼型醇。该程序包括先用硝酸或硝酸与乙酸的混合物进行硝化，然后在尿素存在下进行水解。
• Synthesis of (3-Hydroxyadamantan-1-yl)methanols
  作者：E. A. Ivleva、A. V. Pogulyaiko、Yu. N. Klimochkin

  DOI：10.1134/s107042801809004x

  日期：2018.9

  of adamantan-1-ylmethanols with fuming nitring acid and subsequent reduction of intermediate nitric acid esters with hydrazine hydrate. The title diols have also been obtained by the reduction of 1-nitroxy-3-(nitroxymethyl)adamantanes. The nitroxylation process is accompanied by oxidation with the formation of substituted adamantane-1-carboxylic acids.

  已经开发了一种便利的方法，用于以烟酰胺硝化酸将金刚烷-1-基甲醇硝化并随后用水合肼还原中间体硝酸酯来合成（3-羟基金刚烷-1-基）-甲醇。通过还原1-硝基-3-（硝基甲基）金刚烷也获得了标题二醇。硝基氧化过程伴随着氧化，形成取代的金刚烷-1-羧酸。
• Oxidation of Deactivated Cage Substrates in the System H2SO4–HNO3
  作者：E. A. Ivleva、I. S. Grinʼ、I. S. Uchaev、Yu. N. Klimochkin

  DOI：10.1134/s1070428020030082

  日期：2020.3

  the adamantane series in the system H2SO4–HNO3 have been studied, and the effective rate constants have been determined. The reaction is described by the pseudo-first-order kinetic equation. The primary kinetic isotope effect has been estimated at 2.9±0.3. The rate-determining step of the oxidation process is cleavage of the adamantane C–H bond. The presence of an ethyl group at the bridgehead position

  摘要研究了H 2 SO 4 -HNO 3体系中16种金刚烷系列羧酸酯的氧化动力学 ，并确定了有效的速率常数。该反应由拟一级动力学方程式描述。初步的动力学同位素效应估计为2.9±0.3。氧化过程的决定速率的步骤是金刚烷CH键的断裂。在桥头位置存在乙基会增加金刚烷底物对氧化的反应性，而甲基，乙氧羰基和乙氧羰基甲基会降低反应性。
• (METH)ACRYLIC ACID ESTER COMPOUND AND PRODUCTION METHOD THEREFOR
  申请人：MITSUBISHI GAS CHEMICAL COMPANY, INC.

  公开号：US20170008830A1

  公开（公告）日：2017-01-12

  Provided are a novel alicyclic ester compound and a method for producing a compound of general formula (1) at a high yield from a compound of general formula (2) and a compound of general formula (3). An adamantane compound expressed by general formula (2) and a hydroxyalkyl (meth)acrylate ester compound expressed by general formula (3) are reacted with each other by use of a dehydration condensation agent as a catalyst to obtain an alicyclic ester compound expressed by general formula

  提供了一种新的脂环酯化合物及从一般式(2)和一般式(3)的化合物高产得到一般式(1)化合物的方法。通过使用脱水缩合剂作为催化剂，将一般式(2)表示的金刚烷化合物和一般式(3)表示的羟基烷基（甲基）丙烯酸酯化合物相互反应，得到一种表示为一般式的脂环酯化合物。
• METHOD FOR PRODUCING NOVEL ALI CYCLIC ESTER COMPOUND, NOVEL ALICYCLIC ESTER COMPOUND, (METH)ACRYLIC COPOLYMER PRODUCED BY POLYMERIZING SAID COMPOUND, AND PHOTOSENSITIVE RESIN COMPOSITION USING SAID COPOLYMER
  申请人：MITSUBISHI GAS CHEMICAL COMPANY, INC.

  公开号：US20160355461A1

  公开（公告）日：2016-12-08

  Provided are a resist and a compound for the resist improving the sensitivity, the resolution and the line edge roughness (LER) in a good balance without spoiling basic properties of a chemical amplification resist such as pattern shape, dry etching resistance, heat resistance and the like. Provided are a method for producing an alicyclic ester compound expressed by general formula (1), an alicyclic ester compound expressed by general formula (1), a (meth)acrylic copolymer obtained by polymerization of the alicyclic ester compound, and a photosensitive resin composition containing the (meth)acrylic copolymer. A method for producing an alicyclic ester compound expressed by general formula (1) includes reacting an adamantane compound expressed by general formula (2) with hydroxyalkylamine expressed by general formula (3) to produce an adamantaneamide compound expressed by general formula (4), and then reacting the adamantaneamide compound expressed by general formula (4) with (meth)acrylic acid.

  提供了一种抗蚀剂和化合物，用于在不破坏化学放大抗蚀剂的基本性能（如图案形状、干法蚀刻抗性、耐热性等）的情况下，平衡提高敏感性、分辨率和线边粗糙度（LER）。提供了一种制备由通式（1）表示的脂环酯化合物的方法，一种由通式（1）表示的脂环酯化合物，通过聚合脂环酯化合物得到的（甲）基丙烯酸酯共聚物，以及含有（甲）基丙烯酸酯共聚物的光敏树脂组合物。制备由通式（1）表示的脂环酯化合物的方法包括将由通式（2）表示的金刚烷化合物与由通式（3）表示的羟基烷基胺反应，生成由通式（4）表示的金刚酰胺化合物，然后将由通式（4）表示的金刚酰胺化合物与（甲）基丙烯酸反应。