3-(1-adamantyl)-4-methoxybenzoic acid chloride | 104224-64-8

• 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-(1-adamantyl)-4-methoxybenzoic acid chloride
• 英文别名: 3-(1-adamantyl)-4-methoxybenzoyl chloride；3-(1-adamantyl)-4-methoxy benzoyl chloride；3-adamantyl-4-methoxybenzoyl chloride
• CAS: 104224-64-8
• 化学式: C₁₈H₂₁ClO₂
• 分子量: 304.817
• InChiKey: MDRKJOPPZMFBCL-UHFFFAOYSA-N

物化性质

• 沸点：
  433.8±38.0 °C(Predicted)
• 密度：
  1.225±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(1-adamantyl)-4-methoxybenzoic acid chloride 生成 allyl 4-[3-(1-adamantyl)-4-methoxybenzoyloxy]-2-fluorobenzoate
  参考文献：
  名称：

  SHROOT, BRAHAM;BERNARDON, JEAN-MICHEL;PILGRIM, WILIAM ROBERT

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(1-金刚烷基)-4-甲氧基苯甲酸 在 氯化亚砜 作用下， 以 甲苯 为溶剂， 反应 3.5h， 生成 3-(1-adamantyl)-4-methoxybenzoic acid chloride
  参考文献：
  名称：

  与视黄酸受体亚型结合的配体的合成，结构亲和关系和生物学活性。

  摘要：

  视黄酸受体（RAR）传递类视色素依赖的基因调控，而类视色素的许多生物学作用是通过三种密切相关的受体亚型（RARα，RARβ和RARγ）的结合和激活来介导的。为了研究受体亚型的作用，我们进行了化学合成程序以寻找这些受体的选择性类维生素A。我们使用重组RARα，-β和-γ蛋白质测量受体结合亲和力，并评估F9鼠畸胎癌细胞（F9细胞）中的细胞分化活性。这项研究已经确定了4-取代的-3-（1-金刚烷基）苯基部分是一种新的药效基团，它可以替代天然存在的全反式视黄酸的β-环香叶亚环。研制了两个衍生自一般结构6-（3-叔烷基苯基）-2-萘甲酸（系列I）和4-[（E）-2-（3-叔烷基苯基苯基）丙烯基]苯甲酸（系列II）的化学系列。特别是，我们获得了RAR伽玛选择性衍生物6- [3-（1-金刚烷基）-4-羟苯基] -2-萘甲酸（7）[Ki（RAR alpha）= 6500 nM，Ki（RAR beta）= 2480

  DOI：

  10.1021/jm00026a006

文献信息

• Di(aromatic) compounds and their use in human and veterinary medicine
  申请人：Centre International de Recherches Dermatologiques Galderma (Cird

  公开号：US05387594A1

  公开（公告）日：1995-02-07

  Di(aromatic) compounds corresponding to the following formula: ##STR1## in which: Ar represents either ##STR2## n=1 or 2 or: ##STR3## X represents a divalent radical, Z represents O, S or a divalent radical, and R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 represent a hydrogen atom or various organic radicals, and the salts of the compounds of formula (I) when R.sub.1 is a carboxylic acid function. Use in human and veterinary medicine and in cosmetics.

  对应以下公式的二芳基化合物：##STR1## 其中：Ar代表##STR2## n=1或2或：##STR3## X代表二价基团，Z代表O、S或二价基团，R.sub.1、R.sub.2、R.sub.3、R.sub.4和R.sub.5代表氢原子或各种有机基团，以及当R.sub.1是羧酸功能时，公式（I）化合物的盐。用于人类和兽医学以及化妆品。
• Aromatic esters and thioesters, a process for their preparation and
  申请人：Centre International de Recherches Dermatologiques (C.I.R.D.)

  公开号：US05173289A1

  公开（公告）日：1992-12-22

  Aromatic esters and thioesters of the formula ##STR1## are useful in human and veterinary medicine and in cosmetic formulations. In the formula, X represents oxygen or sulfur, r' and 4" represent hydrogen, lower alkyl, monohydroxyalkyl, polyhydroxyalkyl, aryl or benzyl optionally substituted, the residue of an amino acid or aminated sugar, or taken together form a heterocycle, R.sub.2 represents .alpha., .alpha.'- dissubstituted alkyl having 4-12 carbon atoms or mono- or polycyclic cycloalkyl having 5-12 carbon atoms whose carbon linking carbon is trisubstituted and R.sub.3 and R.sub.4 represent hydrogen or lower alkyl.

  芳香酯和巯酯的化学式为##STR1##，在人类和兽医学以及化妆品配方中具有用途。在该化学式中，X代表氧或硫，r'和r"代表氢、低碳烷基、单羟基烷基、多羟基烷基、芳基或苄基（可选择性取代）、氨基酸残基或氨基糖残基，或者一起形成一个杂环，R.sub.2代表具有4-12个碳原子的α，α'-二取代烷基或具有5-12个碳原子的单环或多环环烷基，其碳键合碳是三取代的，R.sub.3和R.sub.4代表氢或低碳烷基。
• Aromatic esters and thioesters and their use in human or veterinary
  申请人：Centre International De Recherches dermatologiques (CIRD)

  公开号：US04925658A1

  公开（公告）日：1990-05-15

  Aromatic esters and thioesters have the formula ##STR1## wherein X represents oxygen or sulfur, R.sub.1 represents --CH.sub.2 OH, --CH(OH)--CH.sub.3, --COOR.sub.5 or ##STR2## R.sub.5 represents hydrogen, lower alkyl, lower alkenyl, monohydroxyalkyl or polyhydroxyalkyl, r' and r" represent hydrogen, lower alkyl, monohydroxyalkyl, polyhydroxyalkyl, aryl or benzyl optionally substituted, the residue of an amino acid or aminated sugar, or taken together form a heterocycle, R.sub.2 represents .alpha.,.alpha.'-disubstituted alkyl having 4-12 carbon atoms or mono- or polycyclic cycloalkyl having 5-12 carbon atoms whose carbon linking carbon is trisubstituted, R.sub.3 represents hydrogen, lower alkyl, or --Si(CH.sub.3).sub.2 R'.sub.3 wherein R'.sub.3 represents lower alkyl, and R.sub.4 represents hydrogen or lower alkyl, and the salts of these aromatic esters and thioesters of formula (I) when R.sub.5 represents hydrogen. These aromatic esters and thioesters can be used in human and veterinary medicine and in cosmetic formulations.

  芳香酯和硫酯的化学式为##STR1## 其中X代表氧或硫，R.sub.1代表--CH.sub.2 OH，--CH(OH)--CH.sub.3，--COOR.sub.5或##STR2## R.sub.5代表氢，低碳烷基，低碳烯基，单羟基烷基或多羟基烷基，r'和r"代表氢，低碳烷基，单羟基烷基，多羟基烷基，芳基或苄基（可选择性取代），氨基酸或胺基糖的残基，或者结合在一起形成杂环，R.sub.2代表具有4-12个碳原子的α，α'-二取代烷基或具有5-12个碳原子的单环或多环环烷基，其碳连接碳是三取代的，R.sub.3代表氢，低碳烷基，或--Si(CH.sub.3).sub.2 R'.sub.3，其中R'.sub.3代表低碳烷基，R.sub.4代表氢或低碳烷基，以及这些芳香酯和硫酯的盐的化学式（I），当R.sub.5代表氢时。这些芳香酯和硫酯可用于人类和兽医医学以及化妆品配方中。
• Bi-aromatic esters, a process for their preparation and their use in
  申请人：Centre International de Recherces Dermatologiques Galderma (Cird

  公开号：US05200550A1

  公开（公告）日：1993-04-06

  Bi-aromatic esters have the formula ##STR1## wherein R.sub.1 represents H, OH, --CH.sub.3, --CH.sub.2 OH, --CH(OH)CH.sub.3, --COOR.sub.9, ##STR2## or SO.sub.2 R.sub.10 ; R.sub.9 represents H, C.sub.1 -C.sub.6 alkyl or mono or polyhydroxyalkyl; R.sub.10 represents OH, C.sub.1 -C.sub.6 alkyl or ##STR3## r' and r" represent H, C.sub.1 -C.sub.6 alkyl, aryl, aralkyl, mono or polyhydroxyalkyl, or r' and r" taken together form a heterocycle; R.sub.2 represents H, C.sub.1 -C.sub.6 alkyl, OR.sub.9, F or --CF.sub.3 ; R.sub.3, R.sub.4 and R.sub.5 represent H, F, OH, --CH.sub.3, --OCH.sub.3, --CF.sub.3, --COOH or --CH.sub.2 OH; R.sub.6 and R.sub.8 represent H, .alpha.-substituted C.sub.3 -C.sub.15 alkyl, .alpha.,.alpha.'-disubstituted C.sub.4 -C.sub.12 alkyl, C.sub.3 -C.sub.12 cycloalkyl, C.sub.5 -C.sub.12 mono or polycyclic cycloalkyl whose linking carbon is trisubstituted, --SR.sub.11, --SO.sub.2 R.sub.11 or --SOR.sub.11 ; R.sub.11 represents C.sub.1 -C.sub.6 alkyl or cycloalkyl; R.sub.6 and R.sub.8 cannot simultaneously represent H; R.sub.7 represents H, C.sub.1 -C.sub.6 alkyl, alkenyl, alkenyloxy, OR.sub.12 or SR.sub.13 ; R.sub.12 represents H, C.sub.1 -C.sub.6 alkyl or alkenyl; R.sub.3 represents H, C.sub.1 -C.sub.6 alkyl or aralkyl; with the proviso that when R.sub.1 represents ##STR4## and R.sub.2 represents H then: (i) either R.sub.3 and R.sub.4 are other than H or --CH.sub.3, (ii) or R.sub.7 is other than OR.sub.12 and R.sub.6 or R.sub.8 is cycloalkyl having more than 7 carbon atoms, (iii) or R.sub.7 is OR.sub.12 but R.sub.6 and R.sub.8 are other than H, (iv) or R.sub.7 is OR.sub.12 but R.sub.5 is other than H. The bi-aromatic esters are employed in human and veterinary medicine and in cosmetic compositions.

  双芳香酯的化学式为##STR1##其中R.sub.1代表H，OH，--CH.sub.3，--CH.sub.2 OH，--CH(OH)CH.sub.3，--COOR.sub.9，##STR2##或SO.sub.2 R.sub.10；R.sub.9代表H，C.sub.1 -C.sub.6烷基或单或多羟基烷基；R.sub.10代表OH，C.sub.1 -C.sub.6烷基或##STR3##r'和r"代表H，C.sub.1 -C.sub.6烷基，芳基，芳基烷基，单或多羟基烷基，或r'和r"一起形成杂环；R.sub.2代表H，C.sub.1 -C.sub.6烷基，OR.sub.9，F或--CF.sub.3；R.sub.3，R.sub.4和R.sub.5代表H，F，OH，--CH.sub.3，--OCH.sub.3，--CF.sub.3，--COOH或--CH.sub.2 OH；R.sub.6和R.sub.8代表H，α-取代的C.sub.3 -C.sub.15烷基，α，α'-二取代的C.sub.4 -C.sub.12烷基，C.sub.3 -C.sub.12环烷基，C.sub.5 -C.sub.12单环或多环环烷基，其连接碳为三取代，--SR.sub.11，--SO.sub.2 R.sub.11或--SOR.sub.11；R.sub.11代表C.sub.1 -C.sub.6烷基或环烷基；R.sub.6和R.sub.8不能同时代表H；R.sub.7代表H，C.sub.1 -C.sub.6烷基，烯烃基，烯烃氧基，OR.sub.12或SR.sub.13；R.sub.12代表H，C.sub.1 -C.sub.6烷基或烯烃基；R.sub.3代表H，C.sub.1 -C.sub.6烷基或芳基；但有一个例外，当R.sub.1代表##STR4##且R.sub.2代表H时：(i)要么R.sub.3和R.sub.4不是H或--CH.sub.3，(ii)或者R.sub.7不是OR.sub.12且R.sub.6或R.sub.8是具有超过7个碳原子的环烷基，(iii)或者R.sub.7是OR.sub.12但R.sub.6和R.sub.8不是H，(iv)或者R.sub.7是OR.sub.12但R.sub.5不是H。这些双芳香酯在人类和兽医药物以及化妆品配方中被使用。
• Benzimidazole-derived compounds, method for preparing the same, and
  申请人：Centre International de Recherches Dermatologiques Galderma (CIRD

  公开号：US05446059A1

  公开（公告）日：1995-08-29

  Benzimidazole derivatives having general formula (I), wherein R.sub.1 and R.sub.2 are a hydrogen atom, a lower alkyl radical, an OR.sub.4 radical, a lower fluoroalkyl radical or a halogen atom; R.sub.3 is a hydrogen atom, a lower alkyl radical, a halogen, a hydroxyl or a lower alkoxy radical having 1-6 carbon atoms; R.sub.4 is a hydrogen atom, a lower alkyl radical, a benzyl radical or a (II) radical, PO.sub.3 H, SO.sub.3 H or an aminoacid residue; R.sub.7 is a lower alkyl radical, a lower alkoxy radical having 1-6 carbon atoms, a --(CH.sub.2).sub.n --COOH radical where n=1-6, or the radical (III), where r' and r" are a hydrogen atom or a lower alkyl radical, or form, together with the nitrogen atom, a 5 or 6-membered heterocyclic ring optionally interrupted by a heteroatom; R.sub.5 and R.sub.6 are different and represent the OR.sub.8 radical or a mono or polycyclic cycloalkyl radical having 5-12 carbon atoms bound to the phenyl core by a tertiary carbon; R.sub.8 is a hydrogen atom, a lower alkyl radical, an acyl radical having 2-7 carbon atoms, a benzyl radical optionally substituted by one or more halogen atoms, or a benzoyl radical; and salts of said compounds obtained by adding a pharmaceutically acceptable acid or base. Said compounds may be used therapeutically, in particular in relation to inflammatory and/or immunoallergic conditions, and cosmetically to provide body and hair care.

  通式（I）的苯并咪唑衍生物，其中R.sub.1和R.sub.2是氢原子，较低的烷基基团，OR.sub.4基团，较低的氟烷基基团或卤素原子；R.sub.3是氢原子，较低的烷基基团，卤素，羟基或具有1-6个碳原子的较低烷氧基基团；R.sub.4是氢原子，较低的烷基基团，苄基基团或（II）基团，PO.sub.3 H，SO.sub.3 H或氨基酸残基；R.sub.7是较低的烷基基团，具有1-6个碳原子的较低烷氧基基团，--（CH.sub.2）.sub.n--COOH基团，其中n = 1-6，或基团（III），其中r'和r"是氢原子或较低的烷基基团，或与氮原子一起形成5或6元杂环环，可选地由杂原子中断；R.sub.5和R.sub.6不同，表示OR.sub.8基团或由第三级碳原子与苯环结合的具有5-12个碳原子的单环或多环环烷基基团；R.sub.8是氢原子，较低的烷基基团，具有2-7个碳原子的酰基基团，苄基基团，可选地被一个或多个卤素原子取代，或苯甲酰基基团；以及通过添加药学上可接受的酸或碱所获得的该化合物的盐。该化合物可以在治疗上使用，特别是与炎症和/或免疫过敏状况有关，并且可以在美容上用于提供身体和头发护理。