diamantane-1,6-diol | 62297-03-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: diamantane-1,6-diol
• 英文别名: MDT-12；pentacyclo[7.3.1.14,12.02,7.06,11]tetradecane-1,6-diol
• CAS: 62297-03-4
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: ZDTKTUIFQISHLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  diamantane-1,6-diol 在 草酰氯 、 硫酸 作用下， 以 苯 为溶剂， 生成 Diamantan-1.6-dicarbonsaeurechlorid
  参考文献：
  名称：

  A new approach to the construction of diamondoid hydrocarbons. Synthesis of anti-tetramantane

  摘要：

  DOI：

  10.1021/ja00471a041
• 作为产物：
  描述：

  双金刚烷 在 溴 、 硝酸 作用下， 反应 18.33h， 生成 diamantane-1,6-diol
  参考文献：
  名称：

  Vodicka, Ludek; Janku, Josef; Burkhard, Jiri, Collection of Czechoslovak Chemical Communications, 1983, vol. 48, # 4, p. 1162 - 1172

  摘要：

  DOI：

文献信息

• Monoprotection of Diols as a Key Step for the Selective Synthesis of Unequally Disubstituted Diamondoids (Nanodiamonds)
  作者：Hartmut Schwertfeger、Christian Würtele、Michael Serafin、Heike Hausmann、Robert M. K. Carlson、Jeremy E. P. Dahl、Peter R. Schreiner

  DOI：10.1021/jo801321s

  日期：2008.10.3

  (desymmetrization) of diamondoid, benzylic, and ethynyl diols has been achieved using fluorinated alcohols such as 2,2,2-trifluoroethanol (TFE) under acidic conditions. This practical acid-catalyzed S(N)1 reaction opens the door for the synthesis of novel bifunctional diamondoids. With diamantane as an example, we show that the resulting monoethers can be used to prepare selectively, for instance, amino

  使用氟化醇（例如2,2,2-三氟乙醇（TFE））在酸性条件下已实现了类金刚石，苄基和乙炔基二醇的单保护（脱对称）。这种实用的酸催化S（N）1反应为合成新型双功能类金刚石打开了大门。以金刚烷为例，我们表明所得的单醚可用于选择性制备，例如氨基或硝基醇和非天然氨基酸。在探索功能化纳米金刚石的电子，药理和材料特性方面，这些是重要的化合物。
• MONOETHERIFIED DIOLS OF DIAMONDOIDS
  申请人：Schreiner Peter R.

  公开号：US20110124912A1

  公开（公告）日：2011-05-26

  The invention at hand describes functionalized diols of diamondoids, in which one of the two hydroxy groups is masked by a protective group, as well as methods for producing these functionalized diols. The protective group is a group —CHR 1 R 2 , wherein R 1 and R 2 stand for alkyl groups and the protective group comprises at least one halogen atom. The monoethers of the diamondoid diols according to the present invention are produced by reacting the diamondoid diol with a halogenated alcohol CHOHR 1 R 2 in the presence of a catalyst acid. The monoetherified diols allow for the targeted production of derivatives of diamondoids, for example, of the corresponding aminoalcohols and aminocarboxylic acids. For that purpose, the diamondoid monoether is reacted in a first step with a halogen nitrile in a Ritter reaction to the corresponding monoether amide. From this monoether amide, the corresponding aminoalcohol can be produced by reacting the protective group —CHR 1 R 2 first with trifluoroacetic acid to the alkanoyloxy group and by subsequently obtaining the aminoalcohol by reaction with thiourea, ethanol and glacial acetic acid. The aminoalcohol can be reacted with a sulfuric acid/formic acid or oleum/formic acid to the corresponding aminocarboxylic acid. The amino, hydroxy and carboxylic groups of the diamondoids can be converted into many other functional groups.

  这项发明描述了钻石烷的官能化二元醇，其中两个羟基中的一个被保护基掩盖，以及制备这些官能化二元醇的方法。保护基是一个基团—CHR1R2，其中R1和R2代表烷基，保护基包含至少一个卤素原子。根据本发明，钻石烷二元醇的单醚是通过在催化酸的存在下将钻石烷二元醇与卤代醇CHOHR1R2反应而制备的。单醚化的二元醇允许有针对性地生产钻石烷的衍生物，例如相应的氨基醇和氨基羧酸。为此，首先将钻石烷单醚与卤代腈在里特反应中反应得到相应的单醚酰胺。从这个单醚酰胺中，通过将保护基—CHR1R2先与三氟乙酸反应成烷酰氧基，然后通过与硫脲、乙醇和冰醋酸反应获得氨基醇。氨基醇可以与硫酸/甲酸或油酸/甲酸反应成相应的氨基羧酸。钻石烷的氨基、羟基和羧基可以转化为许多其他官能团。
• Synthetic Routes to Aminotriamantanes, Topological Analogues of the Neuroprotector Memantine^®
  作者：Andrey Fokin、Anika Merz、Natalie Fokina、Hartmut Schwertfeger、Shenggao Liu、Jeremy Dahl、Robert Carlson、Peter Schreiner

  DOI：10.1055/s-0028-1087979

  日期：——

  The amino derivatives of diamantane and triamantane, representing close topological analogues of the neuroprotective drug Memantine®, were prepared via amination of the respective carboxylic acids or alcohols. amines - diols - drugs - hydrocarbons - medicinal chemistry

  金刚烷和金刚烷胺的氨基衍生物是神经保护药Memantine®的紧密拓扑类似物，是通过相应的羧酸或醇的胺化反应制备的。 胺-二醇-药物-碳氢化合物-药物化学
• RESIST COMPOSITION FOR NEGATIVE DEVELOPMENT AND METHOD OF FORMING PATTERN THEREWITH
  申请人：Fujifilm Corporation

  公开号：EP2157479A1

  公开（公告）日：2010-02-24

  To provide a resist composition for negative tone development, which can form a pattern having a good profile improved in the pattern undercut and moreover, can reduce the line edge roughness and enhance the in-plane uniformity of the pattern dimension, and a pattern forming method using the same. A resist composition for negative tone development, comprising (A) a resin capable of increasing the polarity by the action of an acid to increase the solubility in a positive tone developer and decrease the solubility in a negative tone developer, (B) a compound capable of generating an acid having an acid dissociation index pKa of -4.0 or less upon irradiation with an actinic ray or radiation, and (C) a solvent; and a pattern forming method using the same.

  提供一种用于负阶调显影的抗蚀剂组合物，该组合物可形成在图案下切处具有良好轮廓改善的图案，此外，还可降低线边粗糙度并提高图案尺寸的平面内均匀性，以及使用该组合物的图案形成方法。 一种用于负阶调显影的抗蚀剂组合物，包括（A）在酸的作用下能够增加极性以提高在正阶调显影剂中的溶解度并降低在负阶调显影剂中的溶解度的树脂，（B）在用辐照射线或辐射照射时能够生成酸解离指数 pKa 为 -4.0 或以下的酸的化合物，以及（C）溶剂；以及使用该组合物的图案形成方法。
• Selective Preparation of Diamondoid Fluorides^[1]
  作者：Hartmut Schwertfeger、Christian Würtele、Heike Hausmann、Jeremy E. P. Dahl、Robert M. K. Carlson、Andrey A. Fokin、Peter R. Schreiner

  DOI：10.1002/adsc.200800787

  日期：2009.5

  Abstractmagnified imageThe selective fluorination of diamantane, triamantane, [121]tetramantane, and [1(2,3)4]pentamantane bromides and alcohols was achieved by using the fluorinating agents silver fluoride (AgF) and diethylaminosulfur trifluoride (DAST). Various mono‐, di‐, tri‐ and even tetrafluorinated diamondoid derivatives were prepared and characterized. We were also able to prepare the amino fluoro and the fluoro alcohol derivatives of diamantane from the corresponding monoprotected diamondoid diols. These reactions can be carried out in a highly selective manner and proceed without isomerizations. The fluorinated, unequally disubstituted derivatives are valuable compounds for the exploration of electronic, pharmacological, and material properties of functionalized diamondoids.