1-(1,1-二甲基庚基)-3-甲氧基苯 | 866398-21-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(1,1-二甲基庚基)-3-甲氧基苯
• 英文名称: 1-(1,1-dimethylheptyl)-3-methoxybenzene
• 英文别名: 1-Methoxy-3-(2-methyloctan-2-yl)benzene
• CAS: 866398-21-2
• 化学式: C₁₆H₂₆O
• 分子量: 234.382
• InChiKey: PHPDUTQEJUPFGJ-UHFFFAOYSA-N

物化性质

• 沸点：
  308.3±21.0 °C(Predicted)
• 密度：
  0.892±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(1,1-二甲基庚基)-3-甲氧基苯 在 2,6-二甲基吡啶 、 sodium tetrahydroborate 、 四丁基氟化铵 、 溴 、 碘 、 三乙基硅基三氟甲磺酸酯 、 对甲苯磺酸 、 magnesium 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 xylene 为溶剂， 反应 10.0h， 生成 3-{(7R,8R)-7-[4-(1,1-dimethylheptyl)-2-methoxyphenyl]-1,4-dioxaspiro[4,5]dec-8-yl}propan-1-ol
  参考文献：
  名称：

  Expedient Synthesis of Potent Cannabinoid Receptor Agonist (−)-CP55,940

  摘要：

  A stereocontrolled synthesis of (-)-CP55,940, a potent cannabinoid receptor agonist, has been attained using a novel aldolization/retroaldolization interconversion strategy, in which a temporarily generated chiral aldol motif plays essential roles.

  DOI：

  10.1021/ol051570c
• 作为产物：
  描述：

  2,6-二甲氧基苯酚 在 palladium on activated charcoal 2,4,6-三甲基吡啶 、 甲烷磺酸 、 丙烷-1-硫醇 、 氢气 、 sodium hydride 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 380.0h， 生成 1-(1,1-二甲基庚基)-3-甲氧基苯
  参考文献：
  名称：

  Expedient Synthesis of Potent Cannabinoid Receptor Agonist (−)-CP55,940

  摘要：

  A stereocontrolled synthesis of (-)-CP55,940, a potent cannabinoid receptor agonist, has been attained using a novel aldolization/retroaldolization interconversion strategy, in which a temporarily generated chiral aldol motif plays essential roles.

  DOI：

  10.1021/ol051570c

文献信息

• Enantioselective Synthesis of (−)-CP-55940 via Ruthenium- Catalyzed Asymmetric Hydrogenation of Ketones
  作者：Li-Jie Cheng、Jian-Hua Xie、Li-Xin Wang、Qi-Lin Zhou

  DOI：10.1002/adsc.201100898

  日期：2012.4.16

  A new and efficient catalytic asymmetric synthesis of the potent cannabinoid receptor agonist (−)‐CP‐55940 has been developed by using ruthenium‐catalyzed asymmetric hydrogenation of racemic α‐aryl ketones via dynamic kinetic resolution (DKR) as a key step. With RuCl2‐SDPs/diamine [SDPs=7,7′‐bis(diarylphophino)‐1,1′‐spirobiindane] catalysts the asymmetric hydrogenation of racemic α‐arylcyclohexanones

  强效的大麻素受体激动剂的新的和有效的催化不对称合成（ - ） - CP-55940已经通过使用的钌催化不对称氢化开发外消旋α -芳基酮通过动态动力学拆分（DKR）作为关键步骤。用RuCl 2 -SDPs /二胺[SDPs = 7,7'-双（二芳基膦基）-1,1'-螺双茚满]催化剂，通过DKR进行外消旋α-芳基环己酮的不对称氢化，可以提供高收率的相应的顺式-β-芳基环己醇。ee高达99.3％，顺式选择性> 99：1 。在环己烷环上的乙烯缩酮基和邻位的底物6的苯环上的-甲氧基对氢化的选择性和反应性影响很小。基于这种高效的不对称酮氢化反应，从市售的3-甲氧基苯甲醛和1,4-环己烯二酮单乙缩醛开始，以13个步骤（最长的线性步骤）合成了（-）-CP-55940，总产率为14.6％。
• Modulator
  申请人：Selwood David

  公开号：US20080262011A1

  公开（公告）日：2008-10-23

  The present invention relates to a compound of formula I, or a pharmaceutically acceptable salt thereof. Formula (I), wherein R 1 and R 2 are each independently H or alkyl; Y is an alkyl group. CONR 3 R 4 , COOR 5 SO 2 NR 16 R 17 , NHSO 2 R 18 or CN; X is an aryl or heteroaryl group, each of which may be optionally substituted with one or more substituents selected from (CH2) m Z where Z is halogen, OH, CN, alkyl, alkoxy, NO 2 , CF 3 , CONR 6 R 7 , CN, NR 8 R 9 , COOR 10 or NHCOR 11 and m is 0 to 3; R 3 to R 11 are each independently H, alkyl or aryl, wherein said alkyl and aryl groups are optionally substituted by one or more substituents selected from halogen, OH, CN, alkyl, alkoxy, NO 2 , CF 3 , CONR 12 R 13 , CN, NH 2 , COOR 14 , NHCOR 15 , and CN; R 12 to R 18 are each independently H or alkyl, more preferably H or Me; n is 1 to 6; wherein the compound is other than 3′,5′-dimethyl-4-(1,1-dimethylheptyl)-1,1′-biphenyl-2-ol. Further aspects of the invention related to the use of such compounds in the preparation of a medicament for the treatment of a muscular disorder, a gastrointestinal disorder, or for controlling spasticity or tremors.

  本发明涉及一种式I化合物或其药学上可接受的盐。式(I)中，R1和R2各自独立地为H或烷基；Y为烷基、CONR3R4、COOR5、SO2NR16R17、NHSO2R18或CN；X为芳基或杂芳基，每个基团可任选地被一个或多个选自(CH2)mZ的取代基取代，其中Z为卤素、OH、CN、烷基、烷氧基、NO2、CF3、CONR6R7、CN、NR8R9、COOR10或NHCOR11，m为0至3；R3至R11各自独立地为H、烷基或芳基，其中所述烷基和芳基基团可任选地被一个或多个选自卤素、OH、CN、烷基、烷氧基、NO2、CF3、CONR12R13、CN、NH2、COOR14、NHCOR15和CN的取代基取代；R12至R18各自独立地为H或烷基，更优选为H或甲基；n为1至6；所述化合物不包括3′,5′-二甲基-4-(1,1-二甲基庚基)-1,1′-联苯-2-醇。本发明的进一步方面涉及此类化合物在制备用于治疗肌肉疾病、胃肠疾病或控制痉挛或震颤的药物中的用途。
• [EN] CANNABINOID DERIVATIVES AND CONJUGATES AND USES THEREOF<br/>[FR] DÉRIVÉS ET CONJUGUÉS DE CANNABINOÏDES ET LEURS UTILISATIONS
  申请人：BEETLEBUNG PHARMA LTD

  公开号：WO2019159168A1

  公开（公告）日：2019-08-22

  The present invention provides cannabinoid derivatives, more specifically cannabidiol (CBD), desoxy-CBD, and desoxy-A9- tetrahydrocannabinol (desoxy-THC) derivatives, which are useful for neuroprotection, treating pain, or treating a disease associated with alpha-1 glycine receptor (alGlyR) and/or alpha-3 glycine receptor (a3GlyR) deficiency; drug conjugates thereof; and methods of use. (Formula I)

  本发明提供了大麻素衍生物，更具体地说是大麻二酚（CBD）、去氧大麻二酚和去氧A9-四氢大麻酚（去氧-THC）衍生物，这些衍生物对神经保护、治疗疼痛或治疗与α-1甘氨酸受体（alGlyR）和/或α-3甘氨酸受体（a3GlyR）缺乏相关的疾病有用；它们的药物共轭物；以及使用方法。（公式I）
• Synthesis and pharmacology of 1-methoxy analogs of CP-47,497
  作者：John W. Huffman、Seon A. Hepburn、Patricia H. Reggio、Dow P. Hurst、Jenny L. Wiley、Billy R. Martin

  DOI：10.1016/j.bmc.2010.06.054

  日期：2010.8

  Three 1-methoxy analogs of CP-47,497 (7, 8, and 19) have been synthesized and their affinities for the cannabinoid CB1 and CB2 receptors have been determined. Although these compounds exhibit selectivity for the CB2 receptor none have significant affinity for either receptor. Modeling and receptor docking studies were carried out, which provide a rationalization for the weak affinities of these compounds

  CP-47,497 的三种 1-甲氧基类似物（7、8和19）已被合成，并且它们对大麻素 CB 1和 CB 2受体的亲和力已被确定。尽管这些化合物对CB 2受体表现出选择性，但对任一受体均没有显着的亲和力。进行了建模和受体对接研究，为这些化合物对任一受体的弱亲和力提供了合理化。
• Novel, potent THC/anandamide (hybrid) analogs
  作者：Caryl Bourne、Sucharita Roy、Jenny L. Wiley、Billy R. Martin、Brian F. Thomas、Anu Mahadevan、Raj K. Razdan

  DOI：10.1016/j.bmc.2007.08.039

  日期：2007.12

  The structure-activity relationship (SAR) of the end pentyl chain in anandamide (AEA) has been established to be very similar to that of Delta(9)-tetrahydrocannabinol (Delta(9)-THC). In order to broaden our understanding of the structural similarities between AEA and THC, hybrid structures 1-3 were designed. In these hybrids the aromatic ring of THC-DMH was linked to the AEA moiety through an ether linkage with the oxygen of the phenol of THC. Hybrid 1 (O-2220) was found to have very high binding affinity to CB1 receptors (K-i = 8.5 nM), and it is interesting to note that the orientation of the side chain with respect to the oxygen in the phenol is the same as in THCs. To further explore the SAR in this series the terminal carbon of the side chain was modified by adding different substituents. Several such analogs were synthesized and tested for their CB1 and CB2 binding affinities and in vivo activity (tetrad tests). The details of the synthesis and the biological activity of these compounds are described. (c) 2007 Elsevier Ltd. All rights reserved.