n-pentyl 2,5-dihydroxybenzoate

• 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: n-pentyl 2,5-dihydroxybenzoate
• 英文别名: n-pentyl gentisate；Pentyl 2,5-dihydroxybenzoate
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: SNICINPKMUFULT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  n-pentyl 2,5-dihydroxybenzoate 在 magnesium sulfate 、 silver(l) oxide 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  La(OTf)3-催化[3+2]环加成反应合成苯并[d]恶唑/苯并呋喃

  摘要：

  La(OTf) 3催化的[3+2]环加成反应通过醌和1,2-二叔丁基-3-(氰胺基)二氮丙啶合成苯并[ d ]恶唑/苯并呋喃(1,3-二叔丁基-2-氰基胍)/乙烯基叠氮化物已被探索。方便地得到了一系列5-羟基苯并呋喃-4-甲酸衍生物和5-羟基苯并[ d ]恶唑-4-甲酸衍生物，收率高，立体选择性好，可用于进一步转化为有价值的化合物。

  DOI：

  10.1021/acs.joc.3c02641
• 作为产物：
  描述：

  戊醇 、 2,5-二羟基苯甲酸 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 生成 n-pentyl 2,5-dihydroxybenzoate
  参考文献：
  名称：

  La(OTf)3-催化[3+2]环加成反应合成苯并[d]恶唑/苯并呋喃

  摘要：

  La(OTf) 3催化的[3+2]环加成反应通过醌和1,2-二叔丁基-3-(氰胺基)二氮丙啶合成苯并[ d ]恶唑/苯并呋喃(1,3-二叔丁基-2-氰基胍)/乙烯基叠氮化物已被探索。方便地得到了一系列5-羟基苯并呋喃-4-甲酸衍生物和5-羟基苯并[ d ]恶唑-4-甲酸衍生物，收率高，立体选择性好，可用于进一步转化为有价值的化合物。

  DOI：

  10.1021/acs.joc.3c02641

文献信息

• Liquid crystalline compounds
  申请人：Rolic AG

  公开号：EP1046631A1

  公开（公告）日：2000-10-25

  The invention provides compounds of formula I: wherein A1 to A4are independently selected from the group consisting hydrogen, a methyl group and a hydrocarbon group containing from 2 to 80 carbon atoms in which one or more carbon atoms are optionally replaced by a heteroatom selected from the group consisting -O-, -S- and -N- with the proviso that firstly no two heteroatoms are joined together and secondly that at least one of A1 to A4 includes a polymerisable group; B1represents a hydrocarbon group containing from 4 to 80 carbon atoms, in which one or more carbon atoms are optionally replaced by a heteroatom selected from the group consisting -O-, -S- and -N- with the proviso that no two heteroatoms are joined together; MG1 and MG2are the same or different and each independently represents an aromatic or non-aromatic carbocyclic or heterocyclic ring system containing from 1 to 80 carbon atoms, with the proviso that firstly at least one of MG1 and MG2 comprises at least two ring systems and secondly, when MG1 and MG2 are identical each of A1 and A2 or A3 and A4 are different. The invention also provides liquid crystalline mixtures and optical or electro-optical devices including compounds of formula (I).

  本发明提供了式I的化合物：其中A1至A4分别选自由氢、甲基和含有2至80个碳原子的烃基，其中一个或多个碳原子可以被选自-O-、-S-和-N-的杂原子替代，但要求首先没有两个杂原子连接在一起，其次A1至A4中至少一个包括可聚合基团；B1表示含有4至80个碳原子的烃基，在其中一个或多个碳原子可以被选自-O-、-S-和-N-的杂原子替代，但要求没有两个杂原子连接在一起；MG1和MG2相同或不同，且每个独立地表示含有1至80个碳原子的芳香或非芳香的碳环或杂环系统，但要求首先至少有一个MG1和MG2包括至少两个环系统，其次当MG1和MG2相同时，A1和A2或A3和A4中的每一个都不同。本发明还提供了液晶混合物和包括式（I）化合物的光学或电光器件。
• DSC Study on Thermotropic Liquid Crystalline Compounds with Alkyl Substituents
  作者：Yiquan Zheng、Shaoping Ren、Youdao Ling、Mangeng Lu

  DOI：10.1080/15421400500376539

  日期：2006.8.1

  of new liquid crystalline epoxy compounds with alkyl substituents from 1 to 15 carbon atoms were characterized by differential scanning calorimetry (DSC). The result showed the length of lateral alkyl substituents of liquid crystalline compounds was the dominant reason for the change of phase behavior. The result implied that TN-I exhibited the odd–even effect when the length of lateral alkyl chains

  通过差示扫描量热法 (DSC) 对一系列具有 1 至 15 个碳原子的烷基取代基的新型液晶环氧化合物进行了表征。结果表明，液晶化合物的侧向烷基取代基的长度是相行为变化的主要原因。结果表明，当横向烷基链的长度从 5 到 8 约为具有末端极性环氧基的介晶核的完全延伸长度的一半时，TN-I 表现出奇偶效应。
• Weissflog, W.; Demus, D., Molecular Crystals and Liquid Crystals (1969-1991), 1985, vol. 129, p. 235 - 244
  作者：Weissflog, W.、Demus, D.

  DOI：——

  日期：——
• Inhibitors of mammalian melanocyte tyrosinase: in vitro comparisons of alkyl esters of gentisic acid with other putative inhibitors
  作者：Ernest V Curto、Cecil Kwong、Heino Hermersdörfer、Hansruedi Glatt、Chie Santis、Victoria Virador、Vincent J Hearing、Thomas P Dooley

  DOI：10.1016/s0006-2952(98)00340-2

  日期：1999.3

  To discover safe and effective topical skin-lightening agents, we have evaluated alkyl esters of the natural product gentisic acid (GA), which is related to our lead compound methyl gentisate (MG), and four putative tyrosinase inhibitors, utilizing mammalian melanocyte cell cultures and cell-free extracts. Desirable characteristics include the ability to inhibit melanogenesis in cells (IC50 < 100 mu g/mL) without cytotoxicity, preferably due to tyrosinase inhibition. Of the six esters synthesized, the smaller esters (e.g. methyl and ethyl) were more effective enzyme inhibitors (IC50 similar to 11 and 20 mu g/mL, respectively). For comparison, hydroquinone (HQ), a commercial skin "bleaching" agent, was a less effective enzyme inhibitor (IC50 similar to 72 mu g/mL), and was highly cytotoxic to melanocytes in vitro at concentrations substantially lower than the IC50 for enzymatic inhibition. Kojic acid was a potent inhibitor of the mammalian enzyme (IC50 similar to 6 mu g/mL), but did not reduce pigmentation in cells. Both arbutin and magnesium ascorbyl phosphate were ineffective in the cell-free and eel-based assays. MG at 100 mu g/mL exhibited a minimal inhibitory effect on DHICA oxidase (TRP-1) and no effect on DOPAchrome tautomerase (TRP 2), suggesting that MG inhibits melanogenesis primarily via tyrosinase inhibition. MG and GA were non-mutagenic at the hprt locus in V79 Chinese hamster cells, whereas Ha was highly mutagenic and cytotoxic. The properties of MG in vitro, including (1) pigmentation inhibition in melanocytes, (2) tyrosinase inhibition and selectivity, (3) reduced cytotoxicity relative to HQ, and (4) rack of mutagenic potential in mammalian cells, establish MG as a superior candidate skin-lightening agent. (C) 1999 Elsevier Science Inc.
• LIQUID CRYSTAL COMPOUNDS
  申请人：Rolic AG

  公开号：EP1187802A1

  公开（公告）日：2002-03-20