1-hydroxy-2-oxaadamantane | 2879-40-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 1-hydroxy-2-oxaadamantane
• 英文别名: 2-oxaadamantane-1-ol；2-oxaadamantan-1-ol；2-oxa-1-adamantanol；1-Hydroxy-2-oxa-adamantan；3-Hydroxy-2-oxa-adamantan；2-oxatricyclo[3.3.1.13,7]decan-1-ol
• CAS: 2879-40-5
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: DOVTWALDTTVCFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-hydroxy-2-oxaadamantane 在 四磷十氧化物 、 磷酸 、 potassium iodide 作用下， 反应 2.0h， 以59%的产率得到7-exo-iodobicyclo<3.3.1>nonan-3-one
  参考文献：
  名称：

  Synthesis of 2-oxaadamantane and 1-aryl-2-oxaadamantanes

  摘要：

  The direct reduction of 1-hydroxy-2-oxaadamantanes derivatives to give 2-oxaadamantanes was unsuccessful. 2-Oxaadamantanes could, however, be prepared from 1-hydroxy-2-oxaadamantes by a ring opening reaction followed by reduction and subsequent ring-closure. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2016.06.027
• 作为产物：
  描述：

  在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 1-hydroxy-2-oxaadamantane
  参考文献：
  名称：

  Synthesis of 2-oxaadamantane and 1-aryl-2-oxaadamantanes

  摘要：

  The direct reduction of 1-hydroxy-2-oxaadamantanes derivatives to give 2-oxaadamantanes was unsuccessful. 2-Oxaadamantanes could, however, be prepared from 1-hydroxy-2-oxaadamantes by a ring opening reaction followed by reduction and subsequent ring-closure. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2016.06.027

文献信息

• Photochemically induced radical alkenylation of C(sp³)–H bonds
  作者：Yuuki Amaoka、Masanori Nagatomo、Mizuki Watanabe、Keisuke Tao、Shin Kamijo、Masayuki Inoue

  DOI：10.1039/c4sc01631a

  日期：——

  The direct alkenylation of C(sp3)–H bonds was achieved by employing benzophenone and 1,2-bis(phenylsulfonyl)ethylene under photo-irradiation conditions. This simple metal-free reaction enables the substitution of heteroatom-substituted methine, methylene and aliphatic C(sp3)–H bonds by (E)-sulfonylalkene units in a highly chemoselective manner. The derived sulfonylalkenes were further converted in a single step to the prenyl derivatives via a second photo-induced radical substitution and to the pyrrole derivatives via cyclization and aromatization steps. The present protocol thus serves as an efficient method for the direct extension of carbon skeletons for the synthesis of structurally complex natural products and pharmaceuticals.

  直接将C(sp3)−H键进行烯基化反应，通过在光照射条件下使用苯甲酮和1,2-双(苯磺酰基)乙烯实现。这一简单的无金属反应以高度化学选择性的方式，实现了杂原子取代的次甲基、亚甲基和脂族C(sp3)−H键被(E)-磺酰基烯烃单元的取代。由此衍生的磺酰基烯烃进一步通过第二次光引发的自由基取代反应一步转化为异戊二烯衍生物，或通过环化芳构化步骤转化为吡咯衍生物。因此，本方案成为一种高效的方法，可直接扩展碳骨架，用于合成结构复杂的天然产物和药物。
• COMPOUNDS CONTAINING AN ALICYCLIE STRUCTURE AND ANTI-TUMOR APPLICATION
  申请人：Xu Lifeng

  公开号：US20140045779A1

  公开（公告）日：2014-02-13

  This invention relates with anti-tumor activities of new compounds containing an adamantyl group or analogs thereof. The invention also relates with the medication applications of anti-tumor and other diseases by this kind of compounds with the combination of S, P, T structures containing adamantyl group and the formation of stereoisomer, tautomers, prodrug, pharmaceutically acceptable salts, complex salts or solvates to their anticancer application and anticancer agents, which have the following general formula:

  这项发明涉及含有金刚烷基团或其类似物的新化合物的抗肿瘤活性。该发明还涉及利用这种含有金刚烷基团的S、P、T结构的化合物与立体异构体、互变异构体、前药、药用盐、复杂盐或溶剂化物的结合来治疗抗肿瘤和其他疾病的药物应用，这些抗肿瘤剂具有以下一般公式：
• Easy synthesis of 7-alkylbicyclo[3.3.1]non-6-en-3-ones by silica gel-promoted fragmentation of 3-alkyl-2-oxaadamant-1-yl mesylates
  作者：Pelayo Camps、Rachid El Achab、Merce` Font-Bardia、Diana Go¨rbig、Jordi Morral、Diego Mun˜oz-Torrero、Xavier Solans、Montserrat Simon

  DOI：10.1016/0040-4020(96)00217-7

  日期：1996.4

  A synthesis of 7-alkylbicyclo[3.3.1]non-6-en-3-ones4b-f and 4j, k by reaction of the corresponding 3-alkyl-2-oxaadamant-1-yl mesylates3 with silica gel in methylene chloride at room temperature, is described. The method failed to give enones4a, g and the related compounds4l, m, what can be rationalized on mechanistic grounds.

  通过使相应的3-烷基-2-氧杂芳基-1-基甲磺酸基酯3与硅胶在亚甲基中的反应，合成7-烷基双环[3.3.1] non-6-en-3-ones 4b-f和4j，k描述了室温下的氯化物。该方法未能给出烯酮4a，g和相关化合物4l，m，可以根据机械原理对其进行合理化。
• Apoptosis inducing adamantyl derivatives and their usage as anti-cancer
  申请人：Galderma Research & Development, S.N.C.

  公开号：US06127415A1

  公开（公告）日：2000-10-03

  The present invention relates to specific adamantyl or adamantyl group derivative containing retinoid compounds induce apoptosis of cancer cells. These adamantyl retinoid derivatives are useful for the treatment of many cancers and solid tumors, especially androgen-independent prostate cancer, skin cancer, pancreatic carcinomas, colon cancer, melanoma, ovarian cancer, liver cancer, small cell lung carcinoma, non-small cell lung carcinoma, cervical carcinoma, brain cancer, bladder cancer, breast cancer, neuroblastoma/glioblastoma, and leukemia. Also, the invention relates to novel adamantyl or adamantyl group derivative compounds which are useful as active agents for the treatment or prevention of keratinization disorders and other dermatological conditions, and other diseases.

  本发明涉及含有特定金刚烷基或金刚烷基衍生物的视黄醇类化合物，可诱导癌细胞凋亡。这些金刚烷基视黄醇衍生物对许多癌症和实体瘤的治疗有用，特别是雄激素非依赖性前列腺癌、皮肤癌、胰腺癌、结肠癌、黑色素瘤、卵巢癌、肝癌、小细胞肺癌、非小细胞肺癌、宫颈癌、脑癌、膀胱癌、乳腺癌、神经母细胞瘤/胶质母细胞瘤和白血病。此外，本发明还涉及新型金刚烷基或金刚烷基衍生物化合物，其用作治疗或预防角化病和其他皮肤病以及其他疾病的活性剂。
• Apoptosis inducing adamantyl derivatives and their usage as anti-cancer agents, especially for cervical cancers and dysplasias
  申请人：Galderma Research & Development S.N.C.

  公开号：US06462064B1

  公开（公告）日：2002-10-08

  The invention relates to the discovery that specific adamantyl or adamantyl group derivatives containing retinoid-related compounds induce apoptosis of cancer cells and therefore may be used for the treatment of cancer, including advanced cancer. Also, the present invention relates to novel adamantyl or adamantyl group derivatives containing retinoid compounds and their usage for treatment and/or prevention of cancer, keratinization disorders, dermatological conditions, and other therapies More specifically, it has been shown that such adamantyl compounds, e.g., 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid, 2-[3-(1-adamantyl)-4-methoxyphenyl]-5-benzimidazole carboxylic acid, and 6-[3-(1-adamantyl)-4,5-methylenedioxyphenyl]-2-naphthoic acid, can be used to treat or prevent cervical cancers and precancers such as cervical dysplasias, including high grade and low grade dysplasias.

  该发明涉及到发现含有类视黄醇相关化合物的特定金刚烷基或金刚烷基衍生物诱导癌细胞凋亡，并因此可用于治疗包括晚期癌症在内的癌症。此外，本发明涉及到新型含有类视黄醇化合物的金刚烷基或金刚烷基衍生物及其用于治疗和/或预防癌症、角化障碍、皮肤病和其他治疗方案的用途。更具体地，已经证明这种金刚烷基化合物，例如6-[3-(1-金刚烷基)-4-甲氧基苯基]-2-萘酸、2-[3-(1-金刚烷基)-4-甲氧基苯基]-5-苯并咪唑羧酸和6-[3-(1-金刚烷基)-4,5-亚甲二氧基苯基]-2-萘酸，可用于治疗或预防宫颈癌和宫颈上皮内瘤变，包括高度和低度上皮内瘤变。