1-Diamantanecarboxylic acid | 30545-18-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-Diamantanecarboxylic acid
• 英文别名: MDT-17；4-Diadamantylcarboxylic acid；pentacyclo[7.3.1.14,12.02,7.06,11]tetradecane-1-carboxylic acid
• CAS: 30545-18-7
• 化学式: C₁₅H₂₀O₂
• 分子量: 232.323
• InChiKey: BUVACXIHXVLWSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Diamantanecarboxylic acid 在 氯化亚砜 作用下， 生成 1-diamantanecarboxylic acid chloride
  参考文献：
  名称：

  Thermodynamic rearrangements of larger polycyclic hydrocarbons derived from the 38.5 and 41.5.degree.C melting dimers of cyclooctatetraene. Crystal and molecular structures of 5-bromoheptacyclo[8.6.0.02,8.03,13.04,11.05,9.012,16]hexadecane (5-bromo-(C2)-bisethanobisnordiamantane), 6,12-dibromoheptacyclo[7.7.0.02,6.03,15.04,12.05,10.011,16]hexadecane, and nonacyclo[11.7.1.12,28.03,16,04,13.05,10.06,14.07,11.015,20]docosane (bastardane)

  摘要：

  DOI：

  10.1021/jo01303a015
• 作为产物：
  描述：

  1-bromodiamantane 生成 1-Diamantanecarboxylic acid
  参考文献：
  名称：

  BURKHARD, J.;JANKU, J.;VODICKA, L., SB. VSCHT PRAZE., 1983, 47, 73-99

  摘要：

  DOI：

文献信息

• Intramolecular C-H Amination Reaction Provides Direct Access to 1,2-Disubstituted Diamondoids
  作者：Radim Hrdina、Fabian M. Metz、Marta Larrosa、Jan-Philipp Berndt、Yevgeniya Y. Zhygadlo、Sabine Becker、Jonathan Becker

  DOI：10.1002/ejoc.201500691

  日期：2015.10

  present a new approach to disubstituted diamondoids from corresponding carboxylic acids. A dirhodium-acetate-catalyzed (1 mol-%) nitrene insertion reaction of sulfamides was, for the first time, applied to intramolecular C–H functionalization reactions of rigid tricyclic frameworks. This straightforward approach enables the effective and regioselective synthesis of a variety of diamondoid-based cyclic

  我们提出了一种从相应的羧酸中提取双取代类金刚石的新方法。磺酰胺的乙酸二铑催化 (1 mol-%) 氮烯插入反应首次应用于刚性三环骨架的分子内 C-H 官能化反应。这种直接的方法能够有效地和区域选择性地合成各种基于金刚石的环状磺酰胺，它们是具有合成价值的构建块。氨基磺酸盐部分的还原脱保护产生相应的 1,3-氨基醇衍生物。通过 KMnO4 氧化磺胺酯部分可提供 1,3-酮醇或亚胺。最后，我们报告了 Vildagliptin® 类似物作为新的抗糖尿病候选药物（DPP-4 抑制剂）的合成。
• Nanodiamonds in sugar rings: an experimental and theoretical investigation of cyclodextrin–nanodiamond inclusion complexes
  作者：Jens Voskuhl、Mark Waller、Sateesh Bandaru、Boryslav A. Tkachenko、Carlo Fregonese、Birgit Wibbeling、Peter R. Schreiner、Bart Jan Ravoo

  DOI：10.1039/c2ob06915f

  日期：——

  We report on the noncovalent interactions of nanodiamond carboxylic acids derived from adamantane, diamantane, and triamantane with β- and γ-cyclodextrins. The water solubility of the nanodiamonds was increased by attaching an aromatic dicarboxylic acid via peptide coupling. Isothermal titration calorimetry experiments were performed to determine the thermodynamic parameters (Ka, ΔH, ΔG and ΔS) for

  我们报道了衍生自纳米金刚石羧酸的非共价相互作用 金刚烷， 金刚烷， 和 金刚烷含β-和γ-环糊精。这水通过肽偶联连接芳族二羧酸可增加纳米金刚石的溶解度。进行了等温滴定热分析实验，以确定宿主-客体夹杂物的热力学参数（K a，ΔH，ΔG和ΔS）。配合物的化学计量始终为1：1。发现较大的纳米金刚石的K a，ΔG和ΔH的夹杂物增加。Δ小号通常是阳性的，特别是对于最大的纳米金刚石。β-环糊精结合所有纳米金刚石，γ-环糊精显然更喜欢体积最大的纳米金刚石。9-三金刚烷羧酸的相互作用显示出有史以来针对γ-环糊精的最强络合常数之一，K a = 5.0×10 5 M -1。为了对这些包合物的可能结构基础有所了解，我们在理论上的B97-D3 / def2-TZVPP水平上进行了密度泛函计算。
• Method for Producing Substituted Diamantanes
  申请人：Schreiner Peter R.

  公开号：US20100036153A1

  公开（公告）日：2010-02-11

  The invention at hand provides at least dinitroxylated diamantanes. In addition, it provides methods for producing substituted diamantanes with high yields and selectivity. According to the invention, dinitroxylated diamantanes are suitable for being reacted with nucleophiles to form the corresponding disubstituted diamantanes. Surprisingly, it was discovered that at least dinitroxylated or hydroxylated diamantanes are rearranged in the presence of a strong acid, creating at least 4,9-nitroxylated or hydroxylated diamantanes. On the basis of this, 4,9-substituted diamantanes are able to be produced in a targeted manner by reaction with further nucleophiles. Thus, the invention at hand provides the following methods according to the present invention for producing at least disubstituted diamantanes: a) at least dinitroxylation, followed by the substitution of all nitroxy groups by a nucleophile or b) at least dinitroxylation, subsequent rearrangement in the presence of a strong acid, after realised rearrangement all nitroxy groups are replaced by a nucleophile or c) at least dinitroxylation, subsequent reaction with water (as nucleophile), rearrangement of the at least dihydroxylated compound in the presence of a strong acid, after realised rearrangement all hydroxy groups are replaced by another nucleophile.

  该发明提供至少二硝基化二莽烷。此外，它提供了一种高产率和选择性生产取代二莽烷的方法。根据该发明，二硝基化的二莽烷适合与亲核试剂反应，形成相应的二取代二莽烷。令人惊讶的是，在强酸存在的情况下发现，至少二硝基化或羟基化的二莽烷会重排，形成至少4,9-硝基化或羟基化的二莽烷。基于此，通过与进一步的亲核试剂反应，可以有针对性地生产4,9-取代的二莽烷。因此，该发明提供了以下根据本发明的方法，用于生产至少二取代的二莽烷：a) 至少二硝基化，然后用亲核试剂替换所有硝基团或b) 至少二硝基化，后在强酸存在下重排，重排后用亲核试剂替换所有硝基团或c) 至少二硝基化，后与水（作为亲核试剂）反应，在强酸存在下重排，重排后用另一亲核试剂替换所有羟基。
• Host–Guest Complexes of Cyclodextrins and Nanodiamonds as a Strong Non‐Covalent Binding Motif for Self‐Assembled Nanomaterials
  作者：Frauke Schibilla、Jens Voskuhl、Natalie A. Fokina、Jeremy E. P. Dahl、Peter R. Schreiner、Bart Jan Ravoo

  DOI：10.1002/chem.201703392

  日期：2017.11.13

  Be our guest! Carboxy- and amino-substituted molecular nanodiamonds (adamantane, diamantane, and triamantane) are excellent guest molecules for β- and γ-cyclodextrin due to their hydrophobicity and symmetry. Additionally, these high-affinity guest molecules are used as non-covalent anchor molecules for the selective self-assembly of cyclodextrin vesicles (see scheme; ConA=concanavalin A).

  成为我们的客人！羧基和氨基取代的分子纳米金刚石（金刚烷，金刚烷和金刚烷）由于其疏水性和对称性，是β-和γ-环糊精的优良客体分子。另外，这些高亲和力的客体分子被用作非共价锚分子，用于环糊精囊泡的选择性自组装（参见方案； ConA ＝伴刀豆球蛋白A）。
• 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