3-(adamantan-1-yl)-4-hydroxybenzaldehyde | 352647-05-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(adamantan-1-yl)-4-hydroxybenzaldehyde
• 英文别名: 4-hydroxy-3-(1-adamantyl)benzaldehyde；3-(adamant-1-yl)-4-hydroxybenzaldehyde；3-(1-adamantanyl)-4-hydroxybenzaldehyde；3-(1-admantyl)-4-hydroxybenzaldehyde；3-(1-adamantyl)-4-hydroxybenzaldehyde
• CAS: 352647-05-3
• 化学式: C₁₇H₂₀O₂
• 分子量: 256.345
• InChiKey: MNVBTDRBEALBKN-UHFFFAOYSA-N

物化性质

• 沸点：
  404.4±38.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 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：

  3-(adamantan-1-yl)-4-hydroxybenzaldehyde 在 palladium on activated charcoal manganese(IV) oxide 、 氢气 、 sodium hydride 、 potassium carbonate 、 三乙胺 、 红铝 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 12.0h， 生成 ethyl 3'-(adamantan-1-yl)-2-(3-(1,3-dioxoisoindolin-2-yl)propoxy)-4'-hydroxybiphenyl-4-carboxylate
  参考文献：
  名称：

  New synthetic approach to atypical retinoids: application of a versatile annulation procedure

  摘要：

  A new approach to an atypical retinoid is presented. The C-15 skeleton was built up by exploiting a step-by-step sequence: the C-9 fragment of an intermediate was homologated by reaction with a C-4 phosphorane, and then submitted to a benzannulation reaction. The last two carbon atoms were inserted by a Wittig reaction with the C-2 phosphorane of ethyl bromoacetate. Manipulation of functional groups was then performed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.12.038
• 作为产物：
  描述：

  1-金刚烷醇 、 对羟基苯甲醛 在 Amberlite 200 (H⁺ form) 作用下， 以 溶剂黄146 为溶剂， 反应 4.0h， 以84%的产率得到3-(adamantan-1-yl)-4-hydroxybenzaldehyde
  参考文献：
  名称：

  Ion-exchange-resin-catalyzed adamantylation of phenol derivatives with adamantanols: Developing a clean process for synthesis of 2-(1-adamantyl)-4-bromophenol, a key intermediate of adapalene

  摘要：

  已经开发出一种清洁的过程，通过商业可获得且可循环利用的离子交换磺酸树脂在醋酸中催化取代酚类化合物与孔雀石醇进行孔雀石化反应合成2-孔雀石基苯酚衍生物。孔雀石化反应的唯一副产物，即水，可以通过在工作过程中添加少量过量的乙酸酐将其转化为溶剂乙酸，使得该过程除了再生离子交换树脂外无废物产生，并有助于催化剂树脂的循环利用。离子交换磺酸树脂催化剂可以通过过滤轻松回收，并在至少十次的直接再利用中没有明显的活性损失。通过这种无废物过程可以制备阿达帕林的关键中间体2-(1-孔雀石基)-4-溴苯酚。

  DOI：

  10.3762/bjoc.8.23

文献信息

• [EN] S1P RECEPTORS MODULATORS AND THEIR USE THEREOF<br/>[FR] MODULATEURS DES RÉCEPTEURS S1P ET LEUR UTILISATION
  申请人：AKAAL PHARMA PTY LTD

  公开号：WO2010043000A1

  公开（公告）日：2010-04-22

  The invention relates to novel compounds that have S1P receptor modulating activity. Further, the invention relates to a pharmaceutical comprising at least one compound of the invention for the treatment of diseases and/or conditions caused by or associated with inappropriate S1P receptor modulating activity or expression, for example, autoimmune response. A further aspect of the invention relates to the use of a pharmaceutical comprising at least one compound of the invention for the manufacture of a medicament for the treatment of diseases and/or conditions caused by or associated with inappropriate S1P receptor modulating activity or expression such as autoimmune response.

  这项发明涉及具有S1P受体调节活性的新化合物。此外，该发明涉及包括本发明中至少一种化合物的药物，用于治疗由不当的S1P受体调节活性或表达引起或相关的疾病和/或病况，例如自身免疫反应。该发明的另一个方面涉及使用包括本发明中至少一种化合物的药物制造药物，用于治疗由不当的S1P受体调节活性或表达引起或相关的疾病和/或病况，如自身免疫反应。
• [EN] S1P RECEPTORS MODULATORS<br/>[FR] MODULATEURS DES RÉCEPTEURS S1P
  申请人：AKAAL PHARMA PTY LTD

  公开号：WO2010042998A1

  公开（公告）日：2010-04-22

  The invention relates to novel compounds that have S1P receptor modulating activity and, preferably, apoptotic activity and/or anti proliferative activity against cancer cells and other cell types. Further, the invention relates to a pharmaceutical comprising at least one compound of the invention for the treatment of diseases and/or conditions caused by or associated with inappropriate S1P receptor modulating activity or expression, for example, cancer. A further aspect of the invention relates to the use of a pharmaceutical comprising at least one compound of the invention for the manufacture of a medicament for the treatment of diseases and/or conditions caused by or associated with inappropriate S1P receptor modulating activity or expression such as cancer.

  该发明涉及具有S1P受体调节活性的新化合物，最好具有对癌细胞和其他细胞类型具有凋亡活性和/或抗增殖活性。此外，该发明涉及包含该发明中至少一种化合物的药物，用于治疗由不当的S1P受体调节活性或表达引起或相关的疾病和/或病况，例如癌症。该发明的另一个方面涉及使用包含该发明中至少一种化合物的药物制备药物，用于治疗由不当的S1P受体调节活性或表达引起或相关的疾病和/或病况，如癌症。
• 一类黄酮衍生物及其制备方法和用途
  申请人：厦门大学

  公开号：CN106220600A

  公开（公告）日：2016-12-14

  一类黄酮衍生物及其制备方法和用途，涉及黄酮衍生物。依次制备2,4‑二羟基‑5‑(1‑金刚烷基)‑苯乙酮、2,5‑二羟基‑3‑(1‑金刚烷基)‑苯乙酮、2‑羟基‑4‑苄氧基‑5‑(1‑金刚烷基)‑苯乙酮、2‑羟基‑5‑苄氧基‑3‑(1‑金刚烷基)‑苯乙酮、4‑羟基‑3‑(1‑金刚烷基)‑苯甲醛、4‑苄氧基‑3‑(1‑金刚烷基)‑苯甲醛、6,7,8‑取代基‑2‑(3,4,5‑取代基苯基)‑二氢色原酮、1‑(2,5‑取代基)‑3‑(3,4‑取代基)‑丙烯酮、8‑取代基‑2‑(3,4‑取代基苯基)‑色原酮、黄酮衍生物。可在制备抗癌药物、抗艾滋病药物和作为组蛋白去乙酰化酶的抑制剂中应用。
• S1P Receptors Modulators
  申请人：Grobelny Damian W.

  公开号：US20120034270A1

  公开（公告）日：2012-02-09

  The invention relates to novel compounds that have S1P receptor modulating activity and, preferably, apoptotic activity and/or anti proliferative activity against cancer cells and other cell types. Further, the invention relates to a pharmaceutical comprising at least one compound of the invention for the treatment of diseases and/or conditions caused by or associated with in-appropriate S1P receptor modulating activity or expression, for example, cancer. A further aspect of the invention relates to the use of a pharmaceutical comprising at least one compound of the invention for the manufacture of a medicament for the treatment of diseases and/or conditions caused by or associated with inappropriate S1P receptor modulating activity or expression such as cancer.

  本发明涉及一种具有S1P受体调节活性的新化合物，优选具有凋亡活性和/或抗癌细胞和其他细胞类型增殖活性。此外，本发明涉及一种药物，包括本发明中至少一种化合物，用于治疗由于或与不适当的S1P受体调节活性或表达相关的疾病和/或状况，例如癌症。本发明的另一方面涉及使用包括本发明中至少一种化合物的药物制造药物，用于治疗由于或与不适当的S1P受体调节活性或表达相关的疾病和/或状况，例如癌症。
• S1P Receptors Modulators and Their Use Thereof
  申请人：Gill Gurmit S.

  公开号：US20110318388A1

  公开（公告）日：2011-12-29

  The invention relates to novel compounds that have S1P receptor modulating activity. Further, the invention relates to a pharmaceutical comprising at least one compound of the invention for the treatment of diseases and/or conditions caused by or associated with inappropriate S1P receptor modulating activity or expression, for example, autoimmune response. A further aspect of the invention relates to the use of a pharmaceutical comprising at least one compound of the invention for the manufacture of a medicament for the treatment of diseases and/or conditions caused by or associated with inappropriate S1P receptor modulating activity or expression such as autoimmune response.

  本发明涉及具有S1P受体调节活性的新化合物。此外，本发明涉及包括本发明中至少一种化合物的药物，用于治疗由不适当的S1P受体调节活性或表达引起或相关的疾病和/或病情，例如自身免疫反应。本发明的另一个方面涉及使用包括本发明中至少一种化合物的药物制造药物，用于治疗由不适当的S1P受体调节活性或表达引起或相关的疾病和/或病情，例如自身免疫反应。