6-formyl-7-hydroxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran | 32268-32-9

• 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-formyl-7-hydroxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran
• 英文别名: 6-formyl-7-hydroxy-2,2-dimethylchroman；7-hydroxy-2,2-dimethyl-6-chromanecarbaldehyde；7-hydroxy-2,2-dimethylchroman-6-carbaldehyde；7-hydroxy-2,2-dimethyl-3,4-dihydrochromene-6-carbaldehyde
• CAS: 32268-32-9
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: UJMNYGMQCPTSKW-UHFFFAOYSA-N

物化性质

• 熔点：
  104 °C
• 沸点：
  319.9±42.0 °C(Predicted)
• 密度：
  1.173±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  6-formyl-7-hydroxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran 在 ammonium cerium (IV) nitrate 、 溶剂黄146 、 N,N-二乙基苯胺 、 potassium hydroxide 作用下， 以 乙醚 、 水 为溶剂， 反应 1.08h， 生成 3-hydroxy-4,4-dimethoxy-2,2-dimethyl-3H-pyrano[3,2-g]chromen-8-one
  参考文献：
  名称：

  Total Synthesis of (±)-Scuteflorin A

  摘要：

  A highly efficient synthesis was developed for the first total synthesis of scuteflorin A. (c) 2010 Elsevier Science. All rights reserved.

  DOI：

  10.3987/com-10-12030
• 作为产物：
  描述：

  dihydroxanthyletin 在 氯仿 、 臭氧 作用下， 生成 6-formyl-7-hydroxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran
  参考文献：
  名称：

  Bell et al., Journal of the Chemical Society, 1937, p. 1542,1544

  摘要：

  DOI：

文献信息

• Functional group manoeuvring for tuning stability and reactivity: synthesis of cicerfuran, moracins (D, E, M) and chromene-fused benzofuran-based natural products
  作者：Maddali L. N. Rao、Venneti N. Murty、Sachchida Nand

  DOI：10.1039/c7ob02459b

  日期：——

  The protecting group manoeuvring as a strategy was applied in tuning the stability and reactivity of substituted gem-dibromovinylphenols (12a and 22) for the domino synthesis of benzofuran-based natural products. (1–8).

  作为一种策略，保护基团操纵被应用于调节取代的gem-二溴乙烯酚（12a和22）的稳定性和反应性，用于苯并呋喃类天然产物的多米诺合成（1–8）。
• Condensation of salicylaldehydes with ethyl 4,4,4-trichloro-3-oxobutanoate: a facile approach for the synthesis of substituted 2H-chromene-3-carboxylates
  作者：Mudulkar Sairam、Gannerla Saidachary、Bhimapaka China Raju

  DOI：10.1016/j.tetlet.2015.01.114

  日期：2015.3

  A highly efficient and simple protocol has been developed for the preparation of ethyl 2-oxo-2H-chromene-3-carboxylates 3a–v by the condensation of salicylaldehydes 1a–v with ethyl 4,4,4-trichloro-3-oxobutanoate 2 for the first time. The reaction is proceeding via Knoevenagel pathway followed by a selective addition of the phenolic hydroxyl group to the carbonyl group adjacent to the CCl3 group rather

  通过将水杨醛1a - v与4,4,4-三氯-3-氧代丁酸乙酯缩合，已开发出一种高效且简单的方案，用于制备2-oxo-2 H-色烯-3-羧酸乙酯3a – v第一次2。该反应通过Knoevenagel途径进行，随后由于强的电子吸收作用，将酚羟基选择性地添加到与CCl 3基团相邻的羰基上而不是酯羰基上，并且生成了香豆素衍生物3a，消除了CHCl 3。
• Synthesis of novel unnatural α-amino acids (UAAs) containing 7-hydroxy-2,2-dimethyl-chroman using isoxazole as a linker
  作者：K. Raghavulu、Ramakrishna Gudipati、K. Basavaiah、Chidananda Swamy Rumalla、Satyanarayana Yennam、Manoranjan Behera

  DOI：10.1039/d1nj01985f

  日期：——

  3-di-polar-cyloaddition reaction has been described. Using this method, various new ethyl 2-amino-3-(3-(7-hydroxy-2,2-dimethylchroman-6-yl)isoxazol-5-yl)propanoate derivatives have been prepared where the isoxazole ring is acting as a linker between alanine and chroman moieties. This is the first example of isoxazole-tethered 2,2-dimethylchroman-amino acid hybrids.

  描述了一种通过1,3-双极性 cyloaddition 反应制备含有 7-羟基-2,2-二甲基色满的非天然 α-氨基酸 (UAA) 的有效和新颖的方法。使用这种方法，已经制备了各种新的 2-氨基-3-(3-(7-羟基-2,2-二甲基色满-6-基)异恶唑-5-基)丙酸乙酯衍生物，其中异恶唑环作为丙氨酸和色满部分之间的接头。这是异恶唑栓系的 2,2-二甲基色满-氨基酸杂合体的第一个例子。
• Wittig homologation of 2-(chloromethyl)-2H-chromen-2-ol derivatives: a new facile synthesis of substituted 2,3-dihydrobenzoxepine-4-carboxylates
  作者：Bhimapaka China Raju、Gannerla Saidachary、Jaladi Ashok Kumar

  DOI：10.1016/j.tet.2012.05.047

  日期：2012.8

  homologation of 2-(chloromethyl)-2H-chromen-2-ol derivatives 2a–t with (ethoxycarbonylmethylene)triphenylphosphorane provided the 2-oxoethylidene-2,3-dihydrobenzoxepine-4-carboxy-lates 3a–t with Z (cis) selectivity. Various basic catalysts were studied for the reaction of 2-(chloromethyl)-2H-chromen-2-ol 2a with the combination of Wittig reagent to provide compound 3b. The reaction of 2-(chloromethyl)-2H-chromen-2-ol

  维蒂希的2-（氯甲基）-2同系ħ -苯并吡喃-2-醇衍生物2A -吨与（乙氧基羰基亚甲基）三苯基正膦中提供的2氧代亚乙基-2,3- dihydrobenzoxepine -4-羧基酸酯3A -吨与Ž（顺）的选择性。研究了各种碱性催化剂，用于2-（氯甲基）-2 H-铬-2-醇2a与Wittig试剂的反应，得到化合物3b。2-（氯甲基）-2 H -chromen-2-ol 2a的反应与其他Wittig试剂，例如亚甲基（三亚苯基）膦和（1-乙氧基羰基亚乙基）三苯基膦，提供了酮衍生物4a而不是2-氧代亚乙基衍生物3b。使酮衍生物4a与Wittig试剂（乙氧基羰基亚甲基）三苯基膦烷反应，得到2，3-二氢苯并二甲苯基-4-羧酸酯3b。本方法是新颖的，直接的，并且是首次报道。
• 벤조퓨란 화합물인 그람니페놀 F, 그람니페놀 G, 시세르푸란, 모루니그롤 C 및 그 유도체의 합성방법
  申请人：Industry Academic Cooperation Foundation, Hallym University 한림대학교 산학협력단(220070195175) BRN ▼221-82-10284

  公开号：KR20170023528A

  公开（公告）日：2017-03-06

  2,4-다이하이드록시벤즈알데하이드, 5-브로모레소르시놀 및 세사몰을 이용하여 천연 벤조퓨란인 그람니페놀 F와 G, 모루니그롤 C와 그 3',5'-다이-O-메틸 유사체 및 시세르푸란을 합성하였다. 본 합성에서는 위치선택적 프레닐화, 라미레즈 gem-다이므로모올레핀화(Ramirez gem-dibromoolefination), 미야우라 붕소화(Miyaura borylation), 스즈키 커플링 반응을 이용하였다. 또한, 이들 화합물의 항염증 효과를 지다당-유도 RAW-264.7 대식세포에서 산화질소 생성 저해실험으로 살펴보았다. 모든 화합물들이 약하거나 보통인 (16~42%) 저해활성을 나타내었고, 세포독성은 없었으며, IC 값은 9.1 to 25.2μM였다.

  使用2,4-二羟基苯甲醛、5-溴苯酚和塞萨莫尔合成了天然苯并呋喃类化合物格拉米苯酚F和G，莫鲁尼格醇C及其3',5'-二-O-甲基同系物以及西色呋喃。该合成过程中采用了位置选择性芳基化、拉米雷兹gem-双溴代烯化、宫浦硼化和铃木偶联反应。此外，通过对这些化合物在巨噬细胞系RAW-264.7中的抗炎作用进行氮氧化物生成抑制实验进行了研究。所有化合物显示出轻度或中度（16~42%）的抑制活性，对细胞无毒性，IC50值在9.1到25.2μM之间。