2,3,5-trimethyl-6-prop-2-en-1-ylphenol | 6626-30-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,3,5-trimethyl-6-prop-2-en-1-ylphenol
• 英文别名: 2-Allyl-3,5,6-trimethyl-phenol；6-Hydroxy-1.2.4-trimethyl-5-allyl-benzol；2,3,5-Trimethyl-6-(prop-2-en-1-yl)phenol；2,3,5-trimethyl-6-prop-2-enylphenol
• CAS: 6626-30-8
• 化学式: C₁₂H₁₆O
• 分子量: 176.258
• InChiKey: IQTYGOVXMFJDGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  2,3,5-trimethyl-6-prop-2-en-1-ylphenol 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 palladium diacetate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 作用下， 以 乙醇 、 水 、 甲苯 、 乙腈 为溶剂， 反应 16.0h， 生成 1-(4-methoxyphenyl)-4-(2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)piperazine
  参考文献：
  名称：

  Discovery of Benzofuran Derivatives that Collaborate with Insulin-Like Growth Factor 1 (IGF-1) to Promote Neuroprotection

  摘要：

  A series of benzofuran derivatives with neuroprotective activity in collaboration with IGF-1 was discovered using a newly developed cell-based assay involving primary neural cells prepared from rat hippocampal and cerebral cortical tissues. A structure activity relationship study identified compound 8 as exhibiting potent activity and brain penetrability. An in vitro pharmacological study demonstrated that although IGF-1 and 8 individually exhibited the neuroprotective effect, the latter acted in collaboration with IGF-1 to enhance neuroprotective activity.

  DOI：

  10.1021/acs.jmedchem.6b00191
• 作为产物：
  描述：

  2,3,5-三甲基苯酚 在 potassium carbonate 、 N,N-二乙基苯胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2,3,5-trimethyl-6-prop-2-en-1-ylphenol
  参考文献：
  名称：

  Discovery of Benzofuran Derivatives that Collaborate with Insulin-Like Growth Factor 1 (IGF-1) to Promote Neuroprotection

  摘要：

  A series of benzofuran derivatives with neuroprotective activity in collaboration with IGF-1 was discovered using a newly developed cell-based assay involving primary neural cells prepared from rat hippocampal and cerebral cortical tissues. A structure activity relationship study identified compound 8 as exhibiting potent activity and brain penetrability. An in vitro pharmacological study demonstrated that although IGF-1 and 8 individually exhibited the neuroprotective effect, the latter acted in collaboration with IGF-1 to enhance neuroprotective activity.

  DOI：

  10.1021/acs.jmedchem.6b00191

文献信息

• Benzofuran derivatives
  申请人：Tsukamoto Tetsuya

  公开号：US20100234357A1

  公开（公告）日：2010-09-16

  The present invention provides a compound represented by the following formula (I): wherein: Ring A represents an optionally substituted piperazine ring, an optionally substituted morpholine ring, or an optionally substituted homopiperazine ring; R 1 and R 2 are the same or different from each other, and represent a hydrogen atom or optionally substituted lower alkyl; R 3 and R 4 are the same or different from each other, and represent a hydrogen atom or halogenated or non-halogenated lower alkyl; R 5 to R 7 are the same or different from each other, and represent a hydrogen atom, hydroxy, optionally substituted lower alkyl, optionally substituted lower alkenyl, optionally substituted lower alkoxy, optionally substituted cycloalkyl, optionally substituted aryl, an optionally substituted aromatic heterocyclic ring, optionally substituted amino, or acyl; and represents a single bond or double bond, or a salt thereof.

  本发明提供了一种由以下式（I）表示的化合物： 其中： 环A代表可选择地取代的哌嗪环、可选择地取代的吗啉环或可选择地取代的同环丙二胺环； R1和R2彼此相同或不同，代表氢原子或可选择地取代的较低烷基； R3和R4彼此相同或不同，代表氢原子或卤代或非卤代的较低烷基； R5到R7彼此相同或不同，代表氢原子、羟基、可选择地取代的较低烷基、可选择地取代的较低烯基、可选择地取代的较低烷氧基、可选择地取代的环烷基、可选择地取代的芳基、可选择地取代的芳香杂环、可选择地取代的氨基或酰基；和 代表单键或双键，或其盐。
• Umwandlung von 6-Methylen-tricyclo[3.2.1.0^2,7]oct-3-en-8-onen mit Ameisensäure in kernmethylierte Phenylessigsäuren
  作者：Jasna Peter-Katalinić、Janos Zsindely、Hans Schmid

  DOI：10.1002/hlca.19740570129

  日期：——

  In a preceding communication [5] it was shown that 1, 5-dimethyl-6-methylene-tricyclo[3.2.1.02,7]oct-3-en-8-one (2) and related tricyclic ketones are converted by strong acids (CF3COOH, FSO3H) into polymethylated tropylium salts with loss of carbon monoxide, e.g. the 1, 2, 4-trimethyltropylium ion 4 from 2 (Scheme 1).

  在先前的文献[5]中，表明1，5-二甲基-6-亚甲基-三环[3.2.1.0 2,7 ] oct-3-en-8-one（2）和相关的三环酮被强力转化酸（CF 3 COOH，FSO 3 1H）与一氧化碳的损失，polymethylated卓鎓盐例如1，2，4-trimethyltropylium离子4从2（方案1）。
• An Efficient p-Thiocyanation of Phenols and Naphthols Using a Reagent Combination of Phenyliodine Dichloride and Lead(II) Thiocyanate.
  作者：Yasuyuki KITA、Yoshifumi TAKEDA、Takayuki OKUNO、Masahiro EGI、Kiyosei IIO、Ken-ichi KAWAGUCHI、Shuji AKAI

  DOI：10.1248/cpb.45.1887

  日期：——

  A combination of PhICl2 and Pb(SCN)2 is effective for the p-selective thiocyanation of various types of p-unsubstituted phenols and naphthols 1 to give p-thiocyanatophenols and naphthols 3. The reaction proceeded at 0°C to room temperature in good to quantitative yields. Twenty-five examples are given, in which various functional groups, such as chloro, allyl, carbonyl, ester, amide, and primary hydroxyl groups, are shown to be compatible with this reaction.

  PhICl2 和 Pb(SCN)2 的组合可有效地对各种类型的对未取代苯酚和萘酚 1 进行对选择性硫氰酸化，从而得到对硫氰酸苯酚和萘酚 3。反应在 0°C 至室温下进行，产率高至定量。文中给出了 25 个例子，表明氯基、烯丙基、羰基、酯基、酰胺基和伯羟基等各种官能团与该反应相容。
• BENZOFURAN DERIVATIVES
  申请人：Tsukamoto Tetsuya

  公开号：US20120046277A1

  公开（公告）日：2012-02-23

  The present invention provides a compound represented by the following formula (I): wherein: Ring A represents an optionally substituted piperazine ring, an optionally substituted morpholine ring, or an optionally substituted bromopiperazine ring; R 1 and R 2 are the same or different from each other, and represent a hydrogen atom or optionally substituted lower alkyl; R 3 and R 4 are the same or different from each other, and represent a hydrogen atom or halogenated or non-halogenated lower alkyl; R 3 to R 7 are the same or different from each other, and represent a hydrogen atom, hydroxy, optionally substituted lower alkyl, optionally substituted lower alkenyl, optionally substituted lower alkoxy, optionally substituted cycloakyl, optionally substituted aryl, an optionally substituted aromatic heterocyclic ring, optionally substituted amino, or acyl; and represents a single bond or double bond, wherein R 2 and R 3 do not exist when carbon atoms respectively adjacent to R 2 : and R 3 form a double bond, and there is no case where all of R 1 to R 7 are hydrogen atoms, and R 1 and R 2 ; may form a ring together with an adjacent carbon atom; or a salt thereof.

  本发明提供了以下式(I)所表示的化合物：其中：环A表示可选取代的哌嗪环、可选取代的吗啡环或可选取代的溴代哌嗪环；R1和R2相同或不同，表示氢原子或可选取代的较低烷基；R3和R4相同或不同，表示氢原子或卤代或非卤代的较低烷基；R3到R7相同或不同，表示氢原子、羟基、可选取代的较低烷基、可选取代的较低烯基、可选取代的较低烷氧基、可选取代的环烷基、可选取代的芳基、可选取代的芳香族杂环环、可选取代的氨基或酰基；表示单键或双键，其中当R2和R3分别相邻的碳原子形成双键时，R2和R3不存在，且不存在R1到R7全为氢原子的情况，R1和R2可以与相邻碳原子共同形成环；或其盐。
• Smith et al., Journal of Organic Chemistry, 1939, vol. 4, p. 340
  作者：Smith et al.

  DOI：——

  日期：——