(E)-6-(3-methoxyphenyl)hex-5-enoic acid | 128577-53-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-6-(3-methoxyphenyl)hex-5-enoic acid
• CAS: 128577-53-7
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: SNHRDAPQGXYBRQ-ZZXKWVIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  (E)-6-(3-methoxyphenyl)hex-5-enoic acid 生成 6-(3'-methoxyphenyl)hexanoic acid
  参考文献：
  名称：

  GAPINSKI, D. MARK;MALLETT, BARBARA E.;FROELICH, LARRY L.;JACKSON, WILLIAM+, J. MED. CHEM., 33,(1990) N0, C. 2807-2813

  摘要：

  DOI：
• 作为产物：
  描述：

  环戊酮 在 三氟甲磺酸 、 对甲苯磺酸 作用下， 以 硝基甲烷 、 环己烷 为溶剂， 反应 1.5h， 生成 (E)-6-(3-methoxyphenyl)hex-5-enoic acid
  参考文献：
  名称：

  通过环烷酮缩酮的位点特异性活化实现芳香羰基的烯化**

  摘要：

  简单的底物设计允许环酮的位点特异性活化，用于芳香族羰基化合物的烯化反应。

  DOI：

  10.1002/anie.202317003

文献信息

• Trisubstituted benzene leukotriene B4 receptor antagonists: Synthesis and structure-activity relationships
  作者：Mitoshi Konno、Takahiko Nakae、Shigeru Sakuyama、Yoshihiko Odagaki、Hisao Nakai、Nobuyuki Hamanaka

  DOI：10.1016/s0968-0896(97)00089-8

  日期：1997.8

  A series of trisubstituted benzenes which demonstrate leukotriene B4 (LTB4, 1) receptor affinity was prepared. Previous trisubstituted benzenes from our laboratory showed high affinity to the LTB4 receptor but demonstrated agonist activity in functional assays. Compound 3a, the initial lead compound of this new series, showed only modest affinity (IC50 = 0.20 microM). However, 3a was a receptor antagonist

  制备了一系列显示白三烯B4（LTB4，1）受体亲和力的三取代苯。我们实验室以前的三取代苯对LTB4受体显示出高亲和力，但在功能测定中显示出激动剂活性。该新系列的初始前导化合物化合物3a仅表现出适度的亲和力（IC50 = 0.20 microM）。但是，3a是一种受体拮抗剂，在高达30 microM时没有明显的激动剂活性。脂质尾部和芳基头部区域的进一步修饰导致3b（ONO-4057）的发现。该化合物无激动剂活性，对LTB4受体具有高亲和力（Ki = 3.7 +/- 0.9 nM）。
• [EN] O-SUBSTITUTED (2R,3R)-3-(3-HYDROXYPHENYL)-2-METHYL-4-PENTENOIC ACIDS AND A METHOD OF OBTAINING THE SAME<br/>[FR] ACIDES (2R, 3R)-3-(3-HYDROXYPHÉNYLE)-2-MÉTHYL-4-PENTÉNOÏQUES O-SUBSTITUÉS ET LEUR PROCÉDÉ D'OBTENTION
  申请人：ZENTIVA KS

  公开号：WO2012089181A1

  公开（公告）日：2012-07-05

  The compounds of general formula II are new and represent important intermediates in the synthesis of tapentadol. In the synthesis of tapentadol of formula I and its pharmaceutically acceptable salts, O-protected (2R,3R)-acids of general formula II, in step A, are reacted in an inert organic solvent with an activating agent, optionally in presence of a catalyst or a base; in step B, the obtained compounds of general formula V, wherein R has the above mentioned meaning and X stands for chlorine or alkoxycarbonyloxyl group O-CO-OR1 or pivaloyloxyl O-CO-t-Bu group, wherein R1 is methyl or ethyl, are reacted with dimethylamine or its salts optionally in presence of a base; in step C, the obtained N, N-dimethylamides of general formula VI, wherein R has the above mentioned meaning, are reduced by means of hydride agents in a suitable solvent; in step D, the produced alkeneamines of general formula VII, wherein R has the above mentioned meaning, are hydrogenated on a metal catalysts in a suitable solvent; and, finally, in step E, the produced alkaneamines of general formula VIII, wherein R has the above mentioned meaning, are O-dealkylated by means of dealkylating agents, and, if required, the obtained tapentadol is converted by the action of a pharmaceutically acceptable acid to respective salts, e.g. hydrochloride.

  通用公式II的化合物是新的，并在tapentadol合成中代表重要的中间体。在通用公式II的O-保护（2R,3R）-酸中，通过步骤A，在惰性有机溶剂中与活化剂反应，可选择性地在催化剂或碱的存在下；在步骤B中，所得到的通用公式V的化合物，其中R具有上述所述含义，X代表氯或烷氧羰氧基O-CO-OR1或戊酰氧基O-CO-t-Bu基团，其中R1为甲基或乙基，与二甲胺或其盐反应，可选择性地在碱的存在下；在步骤C中，所得到的通用公式VI的N，N-二甲基酰胺，其中R具有上述所述含义，通过适当溶剂中的氢化剂还原；在步骤D中，所得到的通用公式VII的烯胺，其中R具有上述所述含义，通过金属催化剂在适当溶剂中进行氢化；最后，在步骤E中，所得到的通用公式VIII的烷胺，其中R具有上述所述含义，通过去烷基化剂进行O-去烷基化，并且如果需要，通过药学上可接受的酸作用将得到的tapentadol转化为相应的盐，例如盐酸盐。
• Benzophenone dicarboxylic acid antagonists of leukotriene B4. 2. Structure-activity relationships of the lipophilic side chain
  作者：D. Mark Gapinski、Barbara E. Mallett、Larry L. Froelich、William T. Jackson

  DOI：10.1021/jm00172a020

  日期：1990.10

  A series of lipophilic benzophenone dicarboxylic acid derivatives were found to inhibit the binding of the potent chemotaxin leukotriene B4 (LTB4) to its receptor on intact human neutrophils. Activity at the LTB4 receptor was determined by using a [3H]LTB4-binding assay. The structure-activity relationship for the lipophilic side chain was systematically investigated. Compounds with n-alkyl side chains of varying lengths were prepared and tested. Best inhibition of [3H]LTB4 binding was observed with the n-decyl derivative. Analogues with alkyl chains terminated with an aromatic ring showed improved activity. The 6-phenylhexyl side chain was optimal. Substitution on the terminal aromatic ring was also evaluated. Methoxyl, methylsulfinyl, and methyl substituents greatly enhanced the activity of the compound. For a given substituent, the para isomer had the best activity. Thus the nature of the lipophilic side chain can greatly influence the ability of the compounds to inhibit the binding of LTB4 to its receptor on intact human neutrophils. The most active compound from this series, 84 (LY223982), bound to the LTB4 receptor with an affinity approaching that of the agonist.
• GAPINSKI, D. MARK;MALLETT, BARBARA E.;FROELICH, LARRY L.;JACKSON, WILLIAM+, J. MED. CHEM., 33,(1990) N0, C. 2807-2813
  作者：GAPINSKI, D. MARK、MALLETT, BARBARA E.、FROELICH, LARRY L.、JACKSON, WILLIAM+

  DOI：——

  日期：——
• Olefination of Aromatic Carbonyls via Site‐Specific Activation of Cycloalkanone Ketals**
  作者：Tuong Anh To、Thanh Vinh Nguyen

  DOI：10.1002/anie.202317003

  日期：2024.1.2

  A simple substrate design allows site-specific activation of cyclic ketones for olefination reaction of aromatic carbonyl compounds.

  简单的底物设计允许环酮的位点特异性活化，用于芳香族羰基化合物的烯化反应。