ethyl 4-hydroxy-3-methylbenzoate | 69747-21-3

• 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: ethyl 4-hydroxy-3-methylbenzoate
• 英文别名: ethyl 3-methyl-4-hydroxybenzoate；4-Hydroxy-3-methyl-benzoesaeure-aethylester；4-Oxy-3-methylbenzoesaeureethylester；4-hydroxy-3-methyl-benzoic acid ethyl ester
• CAS: 69747-21-3
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: JWDKYAFBFMULRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  ethyl 4-hydroxy-3-methylbenzoate 在 氯仿 、 五氯化磷 、 potassium carbonate 、 丙酮 作用下， 生成 4-butoxy-3-methyl-benzoic acid-(1-dimethylaminomethyl-1-methyl-pentylester); hydrochloride
  参考文献：
  名称：

  US2404691

  摘要：

  公开号：
• 作为产物：
  描述：

  4-羟基-3-甲基苯甲酸 生成 ethyl 4-hydroxy-3-methylbenzoate
  参考文献：
  名称：

  Auwers, Chemische Berichte, 1906, vol. 39, p. 3174

  摘要：

  DOI：

文献信息

• Palladium-Catalyzed Aerobic Oxidative Carbonylation of C-H Bonds in Phenols for the Synthesis of <i>p</i> -Hydroxybenzoates
  作者：Vinayak V. Gaikwad、Bhalchandra M. Bhanage

  DOI：10.1002/ejoc.201800538

  日期：2018.6.15

  p‐Hydroxybenzoates were prepared directly from phenols through oxidative carbonylation at activated phenol C–H bonds in a procedure that is free of any requirements for co‐catalyst, co‐solvent or external ligand and uses molecular oxygen as a terminal oxidant for C–H bond oxidation.

  对羟基苯甲酸酯是直接从苯酚中通过活化的酚C–H键上的羰基氧化反应制得的，该工艺无需任何助催化剂，助溶剂或外部配体的要求，而使用分子氧作为CH的末端氧化剂键氧化。
• Synthesis and mesomorphic characterization of some novel steroidal mesogens: A structure–property correlation
  作者：Vanishree Bhat S、V.A. Raghunathan、Sandeep Kumar

  DOI：10.1016/j.molliq.2021.117219

  日期：2021.10

  The steroidal derivatives are found to be extremely good mesogens since their inception. Because of their inherent chirality, they have the potential to induce a wide variety of liquid crystalline phases, including frustrated phases depending upon the structure of the steroidal skeleton and the substituents attached. In this report, a series of novel monoalkoxy and dialkoxy benzoate derivatives of

  发现甾体衍生物自出现以来就是极好的介晶。由于它们固有的手性，它们有可能诱导多种液晶相，包括受阻相，这取决于甾体骨架的结构和连接的取代基。本报告合成了一系列新的麦角甾醇单烷氧基和二烷氧基苯甲酸酯衍生物和一些豆甾醇的单烷氧基衍生物，并研究了它们的介晶性质。衍生物表现出各种中间相，包括 SmA、SmC*、N*、TGB 和蓝相。此外，还研究了这些衍生物中的一些与各种有机溶剂的胶凝能力。此外，这些衍生物的介晶现象已与类似的胆固​​醇对应物进行了比较。
• Tetralin esters of phenols or benzoic acids having retinoid like activity
  申请人：Allergan, Inc.

  公开号：US05130335A1

  公开（公告）日：1992-07-14

  Retinoid-like activity is exhibited by compounds of the formula ##STR1## where the R groups are independently hydrogen, or lower alkyl; A is --C(O)O--, --OC(O)--, --C(O)S--, or --SC(O)--; n is 0-5; and Z is H, --COB where B is --OH or a pharmaceutically acceptable salt, or B is --OR.sub.1 where R.sub.1 is an ester-forming group, or B is --N(R).sub.2 where R is hydrogen or lower alkyl, or Z is --OE where E is hydrogen or an ether-forming group or --COR.sub.2 where R.sub.2 is hydrogen, lower alkyl, phenyl or lower alkyl phenyl, or Z is --CHO or an acetal derivative thereof, or Z is --COR.sub.3 where R.sub.3 is --(CH.sub.2).sub.m CH.sub.3 where m is 0-4 and the sum of n and m does not exceed 4.

  该公式中化合物展现出类似视黄醇的活性，其中R基可以独立地是氢或较低烷基；A是--C(O)O--，--OC(O)--，--C(O)S--或--SC(O)--；n为0-5；Z是H，--COB，其中B为--OH或药用可接受的盐，或者B为--OR.sub.1，其中R.sub.1是酯形成基团，或者B为--N(R).sub.2，其中R为氢或较低烷基，或Z为--OE，其中E为氢或醚形成基团，或--COR.sub.2，其中R.sub.2为氢、较低烷基、苯基或较低烷基苯基，或者Z为--CHO或其缩醛衍生物，或者Z为--COR.sub.3，其中R.sub.3为--(CH.sub.2).sub.m CH.sub.3，其中m为0-4，且n和m的总和不超过4。
• Structure-activity studies of 5-[[4-(4,5-dihydro-2-oxazolyl)phenoxy]alkyl]-3-methylisoxazoles: inhibitors of picornavirus uncoating
  作者：Guy D. Diana、Richard C. Oglesby、Vahan Akullian、Philip M. Carabateas、David Cutcliffe、John P. Mallamo、Michael J. Otto、Mark A. McKinlay、Edward G. Maliski、Stephen J. Michalec

  DOI：10.1021/jm00385a021

  日期：1987.2

  A series of substituted phenyl analogues of 5-[[4-(4,5-dihydro-2-oxazolyl) phenoxy]alkyl]-3-methylisoxazoles has been synthesized and evaluated in vitro against several human rhinovirus (HRV) serotypes. Substituents in the 2-position greatly enhanced activity when compared to the unsubstituted compound. Many of these compounds exhibited mean MICs (MIC) against five serotypes as low as 0.40 microM.

  已经合成了一系列5-[[[4-（4,5-二氢-2-恶唑基）苯氧基]烷基] -3-甲基异恶唑的取代苯基类似物，并在体外针对几种人鼻病毒（HRV）血清型进行了评估。与未取代的化合物相比，位于2位的取代基大大提高了活性。这些化合物中的许多都表现出针对低至0.40 microM的五种血清型的平均MIC（MIC）。平均MIC与MIC80（抑制80％所测试血清型的浓度）相关性很好（r = 0.83）。定量结构-活性关系研究表明，MIC与亲脂性（log P）以及诱导效应（sigma m）和体积因子（MW）密切相关。
• Benzofuranyl-tetrahydropyridines and -piperidines, their acid addition
  申请人：Ciba-Geigy Corporation

  公开号：US04259338A1

  公开（公告）日：1981-03-31

  The present invention provides new benzofuranyl-tetrahydropyridines and -piperidines of the general formula I ##STR1## in which R.sub.1 and R.sub.2 independently of one another are hydrogen or lower alkyl or together are lower alkylene, R.sub.3 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, cyclo-lower alkyl or cyclo-lower alkyl-lower alkyl and Y.sub.1 and Y.sub.2 are each hydrogen or together are an additional bond, and the ring A is not further substituted or is further substituted by lower alkyl, lower alkoxy, halogen with an atomic number not more than 35, cyano or hydroxyl and the pharmaceutically acceptable acid addition salts thereof, and antidepressant preparations containing these compounds. The compounds according to the invention have valuable pharmacological properties. In particular, they inhibit the absorption of serotonin by mesencephalic synaptosomes, the serotonin depletion induced in the brain of rats by H 75/12, the absorption of noradrenalin by mesencephalic synaptosomes in rats and the noradrenalin depletion induced in the brain of rats by H 77/77. In the same dosage they also effect inhibition of monoamino-oxidase in the brain of rats and in the liver of rats. Furthermore, they intensify the "head twitch" induced by 5-hydroxy-tryptophan, and are distinguished by good tolerance. The compounds of the general formula I and their pharmaceutically acceptable acid addition salts can therefore be used as psychopharmaceuticals and in particular as antidepressants.

  本发明提供了新的苯并呋喃基-四氢吡啶和-哌啶，其通式如下：其中R.sub.1和R.sub.2分别独立地是氢或较低的烷基，或者一起是较低的烷基烯，R.sub.3是氢、较低的烷基、较低的烯基、较低的炔基、环-较低的烷基或环-较低的烷基烷基，Y.sub.1和Y.sub.2分别是氢或一起是额外的键合，环A未进一步取代或者进一步取代为较低的烷基、较低的烷氧基、原子序数不超过35的卤素、氰基或羟基，以及其药学上可接受的酸盐，以及含有这些化合物的抗抑郁制剂。根据本发明的化合物具有有价值的药理特性。特别地，它们抑制了松果体突触小体对5-羟色胺的吸收，H 75/12诱导的大鼠脑中的5-羟色胺耗竭，大鼠脑中松果体突触小体对去甲肾上腺素的吸收以及H 77/77诱导的大鼠脑中去甲肾上腺素的耗竭。在相同剂量下，它们还能抑制大鼠脑和肝脏中的单胺氧化酶。此外，它们增强了由5-羟色氨酸引起的“头部抽搐”，并具有良好的耐受性。通式I的化合物及其药学上可接受的酸盐因此可用作心理药物，特别是抗抑郁药物。