2,2-二甲基壬烷-1-醇 | 14250-80-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 2,2-二甲基壬烷-1-醇
• 英文名称: 2,2-Dimethyl-nonanol-(1)
• 英文别名: 2,2-Dimethyl-1-nonanol；2,2-dimethylnonan-1-ol
• CAS: 14250-80-7
• 化学式: C₁₁H₂₄O
• 分子量: 172.311
• InChiKey: VWMHRIWUBVXUKW-UHFFFAOYSA-N

物化性质

• 沸点：
  100-103 °C(Press: 4 Torr)
• 密度：
  0.8392 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,2-二甲基壬烷-1-醇 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 dimethylnonanaldehyde
  参考文献：
  名称：

  Potent Anandamide Analogs:  The Effect of Changing the Length and Branching of the End Pentyl Chain

  摘要：

  To examine the effect of changing the length and branching of the end pentyl chain (C5H11) of anandamide (AN), various analogs 1a-h and 2a-f were synthesized from either the known aldehyde ester 6a or from the alcohol 6b and tested for their pharmacological activity. A reproducible procedure was developed for the conversion of arachidonic acid to 6a or 6b in gram quantities (overall yield 15%). The appropriate tetraene esters 7 were prepared by carrying out a Wittig reaction, between 6a and the ylide generated from the phosphonium salt of the appropriate alkyl halide or between the ylide of 6d (prepared from 6a --> 6b --> 6c --> 6d) and the appropriate alkyl aldehydes. They were then hydrolyzed to the corresponding acids and transformed into AN analogs 1 via their acid chlorides then treated with excess ethanolamine. alpha-Alkylation of esters 7 gave compounds 8 which were hydrolyzed to the corresponding acids. These acids via their acid chlorides and subsequent treatment with excess fluoroethylamine gave the target compounds 2. In this way analogs 1e and 2a-c were synthesized from 6d while all the remaining analogs were prepared from 6a. In order to assess the optimal length of the alkyl terminus, analogs 1a-d were prepared and showed moderately high affinities (18-55 nM). However analogs 1a-c failed to produce significant pharmacological effects at doses up to 30 mg/kg. Analog 1d was found to be a weak partial agonist. The reason for the lack of activity in 1a-c is presently not clear. Like the THCs, the branching of the end pentyl chain in AN (1e-h) increased potency both in in vitro and in vivo activities; the dimethylheptyl (DMH) analog 1e was the most potent in the series. Similar alkyl substitutions were carried out in the fluoro-2-methylanandamide series (2a-f), and all of these analogs had high receptor affinities (1-14 nM), the DMH analog 2a being the most potent. With a few exceptions they showed robust pharmacological effects, and AN-like profiles, It was shown that the SAR of the end pentyl chain in AN is very similar to that of THCs. However, the magnitude of enhanced potency observed when the side chain of THC was changed from straight to branched was not observed when the end chain of AN was similarly changed.

  DOI：

  10.1021/jm970212f
• 作为产物：
  描述：

  1-溴代庚烷 在 lithium aluminium tetrahydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 4.25h， 生成 2,2-二甲基壬烷-1-醇
  参考文献：
  名称：

  Potent Anandamide Analogs:  The Effect of Changing the Length and Branching of the End Pentyl Chain

  摘要：

  To examine the effect of changing the length and branching of the end pentyl chain (C5H11) of anandamide (AN), various analogs 1a-h and 2a-f were synthesized from either the known aldehyde ester 6a or from the alcohol 6b and tested for their pharmacological activity. A reproducible procedure was developed for the conversion of arachidonic acid to 6a or 6b in gram quantities (overall yield 15%). The appropriate tetraene esters 7 were prepared by carrying out a Wittig reaction, between 6a and the ylide generated from the phosphonium salt of the appropriate alkyl halide or between the ylide of 6d (prepared from 6a --> 6b --> 6c --> 6d) and the appropriate alkyl aldehydes. They were then hydrolyzed to the corresponding acids and transformed into AN analogs 1 via their acid chlorides then treated with excess ethanolamine. alpha-Alkylation of esters 7 gave compounds 8 which were hydrolyzed to the corresponding acids. These acids via their acid chlorides and subsequent treatment with excess fluoroethylamine gave the target compounds 2. In this way analogs 1e and 2a-c were synthesized from 6d while all the remaining analogs were prepared from 6a. In order to assess the optimal length of the alkyl terminus, analogs 1a-d were prepared and showed moderately high affinities (18-55 nM). However analogs 1a-c failed to produce significant pharmacological effects at doses up to 30 mg/kg. Analog 1d was found to be a weak partial agonist. The reason for the lack of activity in 1a-c is presently not clear. Like the THCs, the branching of the end pentyl chain in AN (1e-h) increased potency both in in vitro and in vivo activities; the dimethylheptyl (DMH) analog 1e was the most potent in the series. Similar alkyl substitutions were carried out in the fluoro-2-methylanandamide series (2a-f), and all of these analogs had high receptor affinities (1-14 nM), the DMH analog 2a being the most potent. With a few exceptions they showed robust pharmacological effects, and AN-like profiles, It was shown that the SAR of the end pentyl chain in AN is very similar to that of THCs. However, the magnitude of enhanced potency observed when the side chain of THC was changed from straight to branched was not observed when the end chain of AN was similarly changed.

  DOI：

  10.1021/jm970212f

文献信息

• COOLING SENSATION AGENT COMPOSITION, SENSORY STIMULATION AGENT COMPOSITION AND USE OF THE SAME
  申请人：Komatsuki Yasuhiro

  公开号：US20110081393A1

  公开（公告）日：2011-04-07

  Disclosed is a cooling sensation agent composition or sensory stimulation agent composition which contains at least one of diester compounds of dicarboxylic acid represented by the formula (1) wherein A represents CH 2 or CH═CH, n represents an integer of 0 to 4 when A is CH 2 , or 1 when A is CH═CH, B is an alcohol residue having 10 to 18 carbon atoms and containing a para-menthane skeleton, which may have a substituent, and C is an alcohol residue having 6 to 18 carbon atoms, which may have a substituent as well as a flavor or fragrance composition, a beverage, a food product, a perfume or cosmetic product, a toiletry product, daily utensil products or groceries, a fiber, a fiber product, clothes, clothing or a medicine, wherein the cooling sensation agent composition or the sensory stimulation agent composition is compounded.

  本文披露了一种包含以下化学式（1）所代表的二羧酸双酯化合物之一的冷却感剂组合物或感官刺激剂组合物，其中A代表CH2或CH═CH，n代表整数0至4（当A为CH2时）或1（当A为CH═CH时），B是含有10至18个碳原子并含有对蒎烷骨架的醇残基，可能有取代基，C是含有6至18个碳原子的醇残基，可能也有取代基，以及香料或香精组合物、饮料、食品产品、香水或化妆品产品、洗涤用品、日用品或杂货、纤维、纤维制品、衣服、服装或药品，其中复合了冷却感剂组合物或感官刺激剂组合物。
• AMIDE SUBSTITUTED IMIDAZOPYRIDINES, IMIDAZOQUINOLINES, AND IMIDAZONAPHTHYRIDINES
  申请人：Krepski R. Larry

  公开号：US20070219196A1

  公开（公告）日：2007-09-20

  Imidazopyridine, imidazoquinoline, and imidazonaphthyridine compounds having an amide substituent at the 1-position, pharmaceutical compositions containing the compounds, intermediates, and methods of making and methods of use of these compounds as immunomodulators, for modulating cytokine biosynthesis in animals and in the treatment of diseases including viral and neoplastic diseases are disclosed.

  揭示了在1-位置具有酰胺取代基的咪唑吡啶、咪唑喹啉和咪唑萘啶化合物，含有这些化合物的药物组合物，中间体，以及制备这些化合物和使用这些化合物作为免疫调节剂的方法，用于调节动物体内的细胞因子生物合成，以及用于治疗包括病毒性和肿瘤性疾病在内的疾病。
• TOTAL SYNTHESIS AND IMMUNOLOGICAL EVALUATION OF SACCHARIDE MOIETIES OF THE LIPOPOLYSACCHARIDE FROM NEISSERIA MENINGITIDIS
  申请人：MAX-PLANCK-GESELLSCHAFT ZUR FÖRDERUNG DER WISSENSCHAFTEN E.V.

  公开号：US20140234364A1

  公开（公告）日：2014-08-21

  The present invention relates to the total chemical synthesis of the monosaccharide 35 # (R′═H), the disaccharide 36 # (R′≠H; R″═H), the trisaccharide 37 # (R′≠H; R″≠H; R′″≠H) and the tetrasaccharide 1 # (R′≠H; R″≠H; R′″≠H) of the following general formula wherein R represents —Y—NH 2 Y represents a linker R′ is H or R″ is H or R′″ is H or of the lipopolysaccharide from Neisseria meningitidis , as well as to the trisaccharide 37 # and the tetrasaccharide 1 # , to vaccines containing at least one of the saccharides 1 # , 35 # , 36 # , and 37 # and to the use of such vaccine for immunization against diseases caused by infection with bacteria containing the tetrasaccharide α-GlcNAc-(1→2)-α-Hep-( 1→3 )-α-Hep-(1→5)-α-Kdo or the trisaccharide α-Hep-(1→3)-α-Hep-(1→5)-α-Kdo or α-GlcNAc-(1→2)-α-Hep-(1→3)-α-Hep, especially for immunization against meningitis, septicaemia, pneumonia and nasopharyngitis caused by Neisseria meningitidis.

  本发明涉及以下通式中的单糖35#（R' = H）、双糖36#（R'≠H；R"= H）、三糖37#（R'≠H；R"≠H；R'"≠H）和四糖1#（R'≠H；R"≠H；R'"≠H）的全合成，其中R代表-Y-NH2，Y代表连接剂，R'为H或R"为H或R'"为H，以及三糖37#和四糖1#，包含至少其中一种糖的疫苗1#，35#，36#和37#，以及使用这种疫苗免疫预防由于感染含有四糖α-GlcNAc-（1→2）-α-Hep-（1→3）-α-Hep-（1→5）-α-Kdo或三糖α-Hep-（1→3）-α-Hep-（1→5）-α-Kdo或α-GlcNAc-（1→2）-α-Hep-（1→3）-α-Hep的细菌引起的疾病，特别是免疫预防由脑膜炎球菌引起的脑膜炎、败血症、肺炎和鼻咽炎。
• Thickened hypochlorite detergent compositions with improved cleaning performance
  申请人：THE PROCTER & GAMBLE COMPANY

  公开号：EP0635568A1

  公开（公告）日：1995-01-25

  The present invention is a thickened aqueous detergent composition. Said composition contains an alkali metal hypochlorite, an alkali metal salt of a fatty acid, a long chain amine oxide and a short chain surfactant to boost cleaning and a tertiary alcohol to restore viscosity.

  本发明是一种增稠水性洗涤剂组合物。 该组合物含有一种碱金属次氯酸盐、一种脂肪酸碱金属盐、一种长链氧化胺和一种短链表面活性剂以提高清洁度，以及一种叔醇以恢复粘度。
• Volkova,I.A. et al., Journal of applied chemistry of the USSR, 1972, vol. 45, p. 2112 - 2114
  作者：Volkova,I.A. et al.

  DOI：——

  日期：——