6-methoxy-1,2,3,4-tetrahydrobenzopyran-8-carboxaldehyde | 99385-74-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-methoxy-1,2,3,4-tetrahydrobenzopyran-8-carboxaldehyde
• 英文别名: 6-Methoxy-8-chromancarboxaldehyde；6-Methoxy-8-chromanecarbaldehyde；6-methoxy-3,4-dihydro-2H-chromene-8-carbaldehyde
• CAS: 99385-74-7
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: FLWDGGPCKJBWNJ-UHFFFAOYSA-N

物化性质

• 沸点：
  342.2±42.0 °C(Predicted)
• 密度：
  1.179±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-methoxy-1,2,3,4-tetrahydrobenzopyran-8-carboxaldehyde 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 0.08h， 以100%的产率得到6-Methoxy-8-chromanmethanol
  参考文献：
  名称：

  Relevance of Conformational Constraints to the Regioselective Lithiation of Aromatic Diethers. Application to the Convenient Construction of the DEF Tricyclic Subunit of the Austalides

  摘要：

  The lithiation of 29 and 30 is shown to occur at all three sites with a dissimilar kinetic preference. For the dihydrofuran, reaction at the proton labeled H-beta, operates predominantly; in the dihydropyran example, H-alpha is the favored site of deprotonation. These protons represent those that are the most deshielded in the respective H-1 NMR spectra. The same is true for 9 and 19, both of which undergo metalation adjacent to the ring oxygen. No crossover in regioselectivity is observed, presumably because the methoxy substituent is sterically precluded from rotating freely. Mixed complexes (dimers, etc.) or mixed aggregates in low equilibrium concentration are key to understanding the acidification phenomenon of ortho hydrogens. As a consequence of the dominance of regiocontrol by the ring oxygen in 9, a convenient means has been developed for elaboration of the tricyclic eastern sector of the austalide mycotoxins.

  DOI：

  10.1021/jo00087a018
• 作为产物：
  描述：

  2-Bromo-1-(3-bromo-propoxy)-4-methoxy-benzene 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 苯 为溶剂， 反应 1.5h， 生成 6-methoxy-1,2,3,4-tetrahydrobenzopyran-8-carboxaldehyde
  参考文献：
  名称：

  Relevance of Conformational Constraints to the Regioselective Lithiation of Aromatic Diethers. Application to the Convenient Construction of the DEF Tricyclic Subunit of the Austalides

  摘要：

  The lithiation of 29 and 30 is shown to occur at all three sites with a dissimilar kinetic preference. For the dihydrofuran, reaction at the proton labeled H-beta, operates predominantly; in the dihydropyran example, H-alpha is the favored site of deprotonation. These protons represent those that are the most deshielded in the respective H-1 NMR spectra. The same is true for 9 and 19, both of which undergo metalation adjacent to the ring oxygen. No crossover in regioselectivity is observed, presumably because the methoxy substituent is sterically precluded from rotating freely. Mixed complexes (dimers, etc.) or mixed aggregates in low equilibrium concentration are key to understanding the acidification phenomenon of ortho hydrogens. As a consequence of the dominance of regiocontrol by the ring oxygen in 9, a convenient means has been developed for elaboration of the tricyclic eastern sector of the austalide mycotoxins.

  DOI：

  10.1021/jo00087a018

文献信息

• Phenylthiomethyl-6-hydroxy-2,3-dihydrobenzo-pyran and analogs thereof
  申请人：Merck & Co., Inc.

  公开号：US04558067A1

  公开（公告）日：1985-12-10

  Phenylthiomethyl-6-hydroxy-2,3-dihydrobenzopyran and analogs thereof were prepared from an appropriate (6-hydroxy-2,3-dihydro-benzopyran-7-yl) formaldehyde or analog thereof with a substituted thiophenol. These compounds were found to be potent anti-inflammatory agents.

  Phenylthiomethyl-6-羟基-2,3-二氢苯并吡喃及其类似物是通过使用适当的(6-羟基-2,3-二氢苯并吡喃-7-基)甲醛或其类似物与取代硫酚反应制备的。这些化合物被发现具有强效的抗炎作用。
• Substituted 5-hydroxy-2,3-dihydrobenzofurans and analogs thereof useful
  申请人：Merck & Co., Inc.

  公开号：US04563476A1

  公开（公告）日：1986-01-07

  Substituted 5-hydroxy-2,3-dihydrobenzofuran and analogs such as the substituted 6-hydroxy-2,3-dihydrobenzopyrans were prepared from an appropriately substituted (5-hydroxy-2,3-dihydrobenzofuran-6-yl) formaldehyde or analog thereof with an aryl amine followed by reduction. These compounds were found to be potent topical anti-inflammatory agents.

  用适当取代的(5-羟基-2,3-二氢苯并呋喃-6-基)甲醛或类似物与芳基胺反应并还原，制备了取代的5-羟基-2,3-二氢苯并呋喃和类似物，如取代的6-羟基-2,3-二氢苯并吡喃。这些化合物被发现是有效的局部抗炎剂。
• Substituted 5-hydroxy-2,3-dihydrobenzofurans and 6-hydroxy-2,3-dihydrobenzopyrans and analogues thereof useful as anti-inflammatory agents
  申请人：Merck & Co., Inc.

  公开号：EP0150291A1

  公开（公告）日：1985-08-07

  Novel substituted 5-hydroxy-2,3-dihydrobenzofurans and analogs thereof having the general formula and pharmaceutically acceptable salts thereof are disclosed wherein m is an integer ranging from 1 to 4; A is (a) phenyl substituted with (R1)q wherein when there are more than one R' (q > 1) R1 can be the same or different from each other and is (1) hydrogen; (2) halo; (3) loweralkoxy; (4) lower alkylthio; (5) lower alkyl sulfinyl; (6) lower alkyl sulfonyl; (7) unsubstituted or substituted phenyl; loweralkoxy; (8) loweralkyl; (9) loweralkenyl; (10) lower alkanoyl; (11) haloloweralkyl; (12) -COOH or -COOC1-6alkyl; (13) aryl; (14) aryloxy; (15) cyano; (16) hydroxyloweralkyl; (17) halo loweralkanoyl; (18) heteroaryl as defined below; or (19) loweralkanoyloxy; q is an integer ranging from 0 to 5; (b) unsubstituted or substituted heteroaryl selected from a group consisting of: (1) thienyl; (2) benzothienyl; (3) furyl; (4) benzofuryl; (5) pyrryl; (6) indolyl; (7) thiazolyl; (8) benzothiazolyl; (Continuation next page) (9) thiadiazolyl; (10) benzothiadiazolyl; (11) quinolyl; (12) isoquinolyl; (13) pyridyl; (14) pyrazinyl; (15) tetrazolyl; or (16) triazolyl, the heteroaryl above being substituted with one or more of R1. Those compounds are useful as anti-inflammatory agents. A Process for preparing those compounds is also disclosed.

  新型取代的 5-羟基-2,3-二氢苯并呋喃及其类似物通式如下 及其药学上可接受的盐类 其中 m 是 1 至 4 的整数；A 是 (a) 被(R1)q取代的苯基，其中当有一个以上的R'(q>1)时，R1可以相同或不同，并且是 (1) 氢 (2) 卤 (3) 低级烷氧基 (4) 低级烷硫基 (5) 低级烷基亚磺酰基 (6) 低级烷基磺酰基； (7) 未取代或取代的苯基； (8) 低级烷氧基 (8) 低级烷基 (9) 低级烯基 (10) 低级烷酰基 (11) 卤代低烷基； (12) -COOH 或 -COOC1-6 烷基； (13) 芳基 (14) 芳氧基 (15) 氰基 (16) 羟基低级烷基 (17) 卤代低烷氧基 (18) 如下定义的杂芳基；或 (19) 下烷酰氧基； q 是 0 至 5 的整数； (b) 未取代或取代的杂芳基，选自以下组成的组 (1) 噻吩基 (2) 苯并噻吩基 (3) 呋喃基 (4) 苯并呋喃基 (5) 吡咯基 (6) 吲哚基 (7) 噻唑基 (8) 苯并噻唑基； (接下页) (9) 噻二唑基； (10) 苯并噻二唑基； (11) 喹啉基 (12) 异喹啉基 (13) 吡啶基 (14) 吡嗪基 (15) 四唑基；或 (16) 三唑基、 上述杂芳基被一个或多个 R1 取代。 这些化合物可用作抗炎剂。还公开了制备这些化合物的工艺。
• Hammond, Milton L.; Zambias, Robert A.; Chang, Michael N., Journal of Medicinal Chemistry, 1990, vol. 33, # 3, p. 909 - 918
  作者：Hammond, Milton L.、Zambias, Robert A.、Chang, Michael N.、Jensen, Norman P.、McDonald, John、et al.

  DOI：——

  日期：——
• HAMMOND, MILTON L.;ZAMBIAS, ROBERT A.;CHANG, MICHAEL N.;JENSEN, NORMAN P.+, J. MED. CHEM., 33,(1990) N, C. 908-918
  作者：HAMMOND, MILTON L.、ZAMBIAS, ROBERT A.、CHANG, MICHAEL N.、JENSEN, NORMAN P.+

  DOI：——

  日期：——