1-hydroxymethyl-3-methoxycarbonyladamantane | 243145-11-1

• 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-hydroxymethyl-3-methoxycarbonyladamantane
• 英文别名: methyl 3-hydroxymethyltricyclo[3.3.1.1^3,7]decane-1-carboxylate；Methyl 3-hydroxymethyltricyclo[3.3.1.1 3,7]decane-1-carboxylate；methyl 3-(hydroxymethyl)adamantane-1-carboxylate
• CAS: 243145-11-1
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: WWOGKIQOECCXIR-UHFFFAOYSA-N

物化性质

• 沸点：
  310.7±15.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-hydroxymethyl-3-methoxycarbonyladamantane 在 吡啶 、 氯化亚砜 、 四丁基氟化铵 、 potassium hydroxide 、 叔丁醇 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  Design, synthesis and in vitro evaluation of bridgehead fluoromethyl analogs of N-{2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl}-N-(pyridin-2-yl)cyclohexanecarboxamide (WAY-100635) for the 5-HT1A receptor

  摘要：

  Fluorinated analogs that are related to the 5-hydroxytryptamine (5-HT1A) antagonist, N-{2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl}-N-(pyridin-2-yl)cyclohexanecarboxamide (WAY-100635), have been synthesized and their binding affinity for the 5-HT1A receptor and other neurotransmitter receptors (adrenoceptors, sigma receptors, and dopamine receptors), and serotonin transporters was examined in vitro. These ligands were designed to provide a possible potential positron emission tomography (PET) ligand with high metabolic stability. To this end, the cyclohexyl moiety in WAY-100635 and in O-desmethyl WAY-100635 was replaced by a bridge-fused ring (BFR) such as adamantyl, cubyl, bicyclo[2.2.2] octyl and bicyclo[2.2.1]heptyl to reduce the metabolic rate of the amide bond hydrolysis, while a fluoromethyl group was introduced on the other bridgehead of the BFR to prevent defluorination by HE elimination. All synthesized analogs displayed high affinity in the (sub)nanomolar range for the 5-HT1A receptor, comparable to WAY-100635. In addition, 6b, 6c and 6d were reasonably selective to the 5-HT1A receptor over the above mentioned receptors. In human hepatocytes, 6b showed a suitable metabolic stability.In conclusion, the obtained data provides a promising starting point for the synthesis of the corresponding F-18-labeled PET analogs. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.06.023
• 作为产物：
  描述：

  1,3-金刚烷二甲酸 在 甲醇 、 sodium tetrahydroborate 、 氯化亚砜 作用下， 反应 11.0h， 生成 1-hydroxymethyl-3-methoxycarbonyladamantane
  参考文献：
  名称：

  通过可见光促进的 CH 烷基化修饰组氨酸特异性肽

  摘要：

  组氨酸（His）带有独特的杂芳族咪唑侧链，在多肽和蛋白质中发挥着不可替代的功能作用。现有的位点选择性组氨酸修饰策略主要依赖于适度亲核的咪唑基团的 N 取代反应，其固有地受到赖氨酸和半胱氨酸残基的干扰。组氨酸的化学选择性修饰仍然是肽化学中最困难的挑战之一。在此，我们报告了在可见光促进条件下使用 C4-烷基-1,4-二氢吡啶 (DHP) 试剂通过自由基介导的化学选择性 CH 烷基化组氨酸进行肽修饰。该方法通过 Minisci 型反应途径利用咪唑环的亲电反应性。该方法对肽和 DHP 烷基化试剂表现出异常广泛的范围。其效用已在一系列重要的肽药物、复杂的天然产物和小蛋白质中得到证明。与 N 取代反应不同，改性咪唑环的未取代氮基团在 CH 烷基化产物中是保守的。

  DOI：

  10.1021/jacs.9b09127

文献信息

• 4-(2-Furoyl) aminopiperidine compound useful as therapeutic agent for itching
  申请人：Muraki Yukiko

  公开号：US20060270632A1

  公开（公告）日：2006-11-30

  There are provided compounds represented by the following general formula (I): [where R 1 is 5-methylpyridin-2-yl, p-tolyl or mesityl, R 2 is one of the following general formulas (II)-(IX): (where R 3 is C1-C4 alkyl, R 4 is H or C1-C4 alkyl, R 5 is H, 3-pyridylmethyl or 4-pyridylmethyl, and R 6 is 2,4-dihydroxybenzyl, 3-pyridylmethyl or 4-pyridylmethyl), or when R 1 is mesityl, R 2 is the following formula (X)], and pharmaceutically acceptable salts thereof. The compounds exhibit pruritus-inhibiting action, and are useful for prevention or treatment of itching and pruritus caused by reaction against insect-inflicted wounds, reaction against environmental allergens, skin infections or external parasite infections, or caused to renal dialysis patient.

  提供了以下通式（I）所代表的化合物：[其中R1为5-甲基吡啶-2-基、对甲基苯基或二甲基苯基，R2为以下通式（II）-（IX）之一：（其中R3为C1-C4烷基，R4为H或C1-C4烷基，R5为H、3-吡啶甲基或4-吡啶甲基，R6为2,4-二羟基苯甲基、3-吡啶甲基或4-吡啶甲基），或当R1为二甲基苯基时，R2为以下通式（X）]，以及其药学上可接受的盐。这些化合物具有抑制瘙痒作用，可用于预防或治疗由对昆虫造成的伤口反应、对环境过敏原的反应、皮肤感染或外部寄生虫感染引起的瘙痒和瘙痒，或透析患者引起的瘙痒。
• 4-(2-furoyl)aminopiperidine compound useful as therapeutic agent for itching
  申请人：Kyorin Pharmaceutical Co., Ltd

  公开号：US07601843B2

  公开（公告）日：2009-10-13

  There are provided compounds represented by the following general formula (I): [where R1 is 5-methylpyridin-2-yl, p-tolyl or mesityl, R2 is one of the following general formulas (II)-(IX): (where R3 is C1-C4 alkyl, R4 is H or C1-C4 alkyl, R5 is H, 3-pyridylmethyl or 4-pyridylmethyl, and R6 is 2,4-dihydroxybenzyl, 3-pyridylmethyl or 4-pyridylmethyl), or when R1 is mesityl, R2 is the following formula (X)], and pharmaceutically acceptable salts thereof. The compounds exhibit pruritus-inhibiting action, and are useful for prevention or of itching and pruritus caused by reaction against insect-inflicted wounds, reaction against environmental allergens, skin infections or external parasite infections, or caused to renal dialysis patient.

  以下是通用式（I）所代表的化合物：[其中R1是5-甲基吡啶-2-基，对甲基苯基或三甲基苯基，R2是以下通用式（II）-（IX）之一：（其中R3是C1-C4烷基，R4是H或C1-C4烷基，R5是H，3-吡啶甲基或4-吡啶甲基，R6是2,4-二羟基苯甲基，3-吡啶甲基或4-吡啶甲基），或当R1是三甲基苯基时，R2是以下式子（X）]，以及其药学上可接受的盐。这些化合物具有止痒作用，可用于预防或治疗由昆虫叮咬引起的瘙痒和瘙痒反应，环境过敏原引起的反应，皮肤感染或外部寄生虫感染引起的瘙痒，或透析患者引起的瘙痒。
• Ligand enabled none-oxidative decarbonylation of aliphatic aldehydes
  作者：Bo Li、Shihao Liu、Wu Fan、Xiaotong Shen、Jing Xu、Suhua Li

  DOI：10.1016/j.cclet.2022.108027

  日期：2022.11

  example of Ir(I)-catalyzed direct decarbonylation of α-quaternary aldehydes with broad substrate scope and good functional group compatibility via judicious selection of ligand. The α-chirality is memorized in this decarbonylation process. In addition, we report a broad-spectrum decarbonylation of α-secondary and α-tertiary aldehydes containing multifunctional groups with an improved Rh(I)/DPPP recipe

  醛的脱羰是一种基本的有机转化，已经发展了六十多年。然而，与研究充分的芳香醛相比，脂肪醛催化脱羰的例子较少，主要是在简单或特殊的底物上。对于α大体积或高度功能化的化合物，通常需要化学计量的 Rh(I) 才能获得不错的产量。在此，我们展示了 Ir(I) 催化的α-季醛直接脱羰基的罕见例子，该例子通过明智地选择配体，具有广泛的底物范围和良好的官能团相容性。α-手性在这个脱羰过程中被记住。此外，我们报告了广谱脱羰基作用含有多功能基团的α-仲醛和α-叔醛，具有改进的 Rh(I)/DPPP 配方。最后，我们通过反应性差异实现了在α-季醛存在下选择性脱羰α-叔醛。
• Adamantane derivative
  申请人：DAICEL CHEMICAL INDUSTRIES, LTD.

  公开号：EP1574494A1

  公开（公告）日：2005-09-14

  In the presence of an imide compound (e.g., N-hydroxyphthalimide) shown by the following formula (1):    wherein R1 and R2 represent a hydrogen atom, a halogen atom, an alkyl group, an aryl group and a cycloalkyl group, and R1 and R2 may bond together to form a double bond, or an aromatic or non-aromatic ring, and Y is an O or OH, and n denotes 1 to 3; a substrate is allowed to contact with at least one reactant selected from (i) a nitrogen oxide and (ii) a mixture of carbon monoxide and oxygen to be introduced with at least one functional group selected from a nitro group and a carboxyl group. The nitrogen oxide includes, for example, a compound represented by the formula NxOy (e.g., N2O3, NO2). The substrate includes, for example, a compound having a methine carbon atom (e.g., adamantane), a compound having a methyl group or a methylene group at an adjacent moiety of an aromatic ring. According to such reaction, the substrate can be efficiently nitrated or carboxylated even in a mild or moderate condition.

  在存在下式（1）所示的酰亚胺化合物（如 N-羟基邻苯二甲酰亚胺）的情况下： 其中 R1 和 R2 代表氢原子、卤素原子、烷基、芳基和环烷基，R1 和 R2 可键合在一起形成双键或芳香环或非芳香环，Y 是 O 或 OH，n 表示 1 至 3； 让基质与至少一种反应物接触，该反应物选自 (i) 氮氧化物和 (ii) 一氧化碳和氧的混合物，并引入至少一种选自硝基和羧基的官能团。例如，氮氧化物包括由式 NxOy 表示的化合物（如 N2O3、NO2）。底物包括例如具有甲基碳原子的化合物（如金刚烷）、在芳香环的相邻分子上具有甲基或亚甲基的化合物。根据这种反应，底物即使在温和或中等条件下也能被有效地硝化或羧化。
• Adamantane derivatives
  申请人：DAICEL CHEMICAL INDUSTRIES, LTD.

  公开号：EP1574495A1

  公开（公告）日：2005-09-14

  An adamantane derivative shown by the following formula (2):

  下式（2）所示的金刚烷衍生物：