3-(2,2-dimethyl-2H-chromen-6-yl)propan-1-ol | 1242080-47-2

• 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: 3-(2,2-dimethyl-2H-chromen-6-yl)propan-1-ol
• 英文别名: 3-(2,2-Dimethylchromen-6-yl)propan-1-ol
• CAS: 1242080-47-2
• 化学式: C₁₄H₁₈O₂
• 分子量: 218.296
• InChiKey: NZPYVTDTWPNLBM-UHFFFAOYSA-N

物化性质

• 沸点：
  355.4±41.0 °C(predicted)
• 密度：
  1.060±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(2,2-dimethyl-2H-chromen-6-yl)propan-1-ol 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.5h， 生成 [3-(2,2-dimethyl-2H-chromen-6-yl)propyl]isopropylamine
  参考文献：
  名称：

  New Class of Algicidal Compounds and Fungicidal Activities Derived from a Chromene Amide of Amyris texana

  摘要：

  A chromene amide, N-[2-(2,2-dimethyl-2H-1-benzopyran-6-yl)ethyl]-N,3-dimethylbutanamide, was isolated from the EtOAc extract of the leaves of Amyris texana and found to have moderate antifungal activity against Colletotrichum spp. and selective algicidal activity against Planktothrix perornata, a cyanobacterium (blue-green alga) that causes musty off-flavor in farm-raised channel catfish (Ictalurus punctatus). To improve the selective algicidal activity and provide water solubility, a series of chromene analogues were synthesized and evaluated for algicidal activity using a 96-well microplate rapid bioassay. In addition, the chromene analogues were evaluated for antifungal and phytotoxic activities. Hydrochloride salts of a chromene amine analogue showed improved water solubility and selectivity toward P. perornata with activity comparable to that of the naturally occurring chromene amide.

  DOI：

  10.1021/jf101626g
• 作为产物：
  描述：

  对羟基苯丙酸甲酯 在 lithium aluminium tetrahydride 、 potassium carbonate 、 N,N-二乙基苯胺 、 potassium iodide 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 52.5h， 生成 3-(2,2-dimethyl-2H-chromen-6-yl)propan-1-ol
  参考文献：
  名称：

  New Class of Algicidal Compounds and Fungicidal Activities Derived from a Chromene Amide of Amyris texana

  摘要：

  A chromene amide, N-[2-(2,2-dimethyl-2H-1-benzopyran-6-yl)ethyl]-N,3-dimethylbutanamide, was isolated from the EtOAc extract of the leaves of Amyris texana and found to have moderate antifungal activity against Colletotrichum spp. and selective algicidal activity against Planktothrix perornata, a cyanobacterium (blue-green alga) that causes musty off-flavor in farm-raised channel catfish (Ictalurus punctatus). To improve the selective algicidal activity and provide water solubility, a series of chromene analogues were synthesized and evaluated for algicidal activity using a 96-well microplate rapid bioassay. In addition, the chromene analogues were evaluated for antifungal and phytotoxic activities. Hydrochloride salts of a chromene amine analogue showed improved water solubility and selectivity toward P. perornata with activity comparable to that of the naturally occurring chromene amide.

  DOI：

  10.1021/jf101626g

文献信息

• Catalytic C(sp³)–H Alkylation via an Iron Carbene Intermediate
  作者：Jennifer R. Griffin、Chloe I. Wendell、Jacob A. Garwin、M. Christina White

  DOI：10.1021/jacs.7b07602

  日期：2017.10.4

  transformation of a C(sp3)-H bond to a C(sp3)-C bond via an iron carbene intermediate represents a long-standing challenge. Despite the success of enzymatic and small molecule iron catalysts mediating challenging C(sp3)-H oxidations and aminations via high-valent iron oxos and nitrenes, C(sp3)-H alkylations via isoelectronic iron carbene intermediates have thus far been unsuccessful. Iron carbenes have

  通过铁卡宾中间体将 C(sp3)-H 键催化转化为 C(sp3)-C 键是一项长期存在的挑战。尽管酶促和小分子铁催化剂通过高价铁氧代和氮烯介导具有挑战性的 C(sp3)-H 氧化和胺化取得了成功，但通过等电子铁卡宾中间体进行的 C(sp3)-H 烷基化迄今尚未成功。铁卡宾是惰性的，或显示有利于烯烃环丙烷化和杂原子-氢插入。在此我们报告了铁酞菁催化的烯丙基和苄基 C(sp3)-H 键的烷基化。机理研究支持亲电铁卡宾介导均裂 CH 裂解并从所得有机铁中间体反弹形成 CC 键；这两个步骤都可以通过催化剂修饰进行调节。