2,2-dimethyl-6-phenyl-2H-chromene | 82305-05-3

• 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: 2,2-dimethyl-6-phenyl-2H-chromene
• 英文别名: 2,2-Dimethyl-6-phenyl-chromene；2,2-dimethyl-6-phenylchromene
• CAS: 82305-05-3
• 化学式: C₁₇H₁₆O
• 分子量: 236.313
• InChiKey: DUQLGXOYHFFGOP-UHFFFAOYSA-N

物化性质

• 熔点：
  53-55 °C(Solv: ethanol (64-17-5))
• 沸点：
  367.9±42.0 °C(Predicted)
• 密度：
  1.053±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-6-phenyl-2H-chromene 在 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 、 水 、 sodium hydride 作用下， 以 乙醚 、 二甲基亚砜 为溶剂， 反应 1.0h， 生成 1-((3S,4R)-3-Hydroxy-2,2-dimethyl-6-phenyl-chroman-4-yl)-pyrrolidin-2-one
  参考文献：
  名称：

  Variation in the aromatic ring of cromakalim: antihypertensive activity of pyranopyridines and 6-alkyl-2H-1-benzopyrans

  摘要：

  The synthesis and antihypertensive activity in the spontaneously hypertensive rat of two new series of analogues related to cromakalim (1) are described. In the first series, where the benzopyran nucleus has been replaced by a pyranopyridine nucleus, the position of the nitrogen atom has been found to be critical for activity, and the most potent compounds are the pyrano[3,2-c]pyridines. In the second series, where the powerful electron-withdrawing cyano group of compound 1 has been replaced by alkyl and phenyl groups, the order of antihypertensive potency is ethyl, isopropyl, tert-butyl greater than propyl, cyclopentyl greater than methyl greater than phenyl.

  DOI：

  10.1021/jm00173a018
• 作为产物：
  描述：

  对羟基联苯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 copper dichloride 作用下， 以 邻二氯苯 、 乙腈 为溶剂， 反应 17.0h， 生成 2,2-dimethyl-6-phenyl-2H-chromene
  参考文献：
  名称：

  Synthesis and antimycobacterial evaluation of benzofurobenzopyran analogues

  摘要：

  We recently reported that 3,3-dimethyl-3H-benzofuro[3,2,f][1]-benzopyran and its hydrogenated analogue are selective in vitro inhibitors of mycobacterial growth. However, their lack of in vivo activity on a murine model of Mycobacterium tuberculosis infection due to their poor bioavailability led to a structure-activity relationship investigation. We wish to report here the preparation of some structural analogues along with their biological effect on the growth of Mycobacterium smegmatis, M. tuberculosis, as well as on VERO cells for the most active compound. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.12.009

文献信息

• Asymmetric Counteranion-Directed Transition-Metal Catalysis: Enantioselective Epoxidation of Alkenes with Manganese(III) Salen Phosphate Complexes
  作者：Saihu Liao、Benjamin List

  DOI：10.1002/anie.200905332

  日期：2010.1.12

  Paired up: A highly active and enantioselective ion‐pair epoxidation catalyst, consisting of an achiral MnIII–salen complex and a chiral phosphate counteranion, mediates the epoxidization of a wide range of alkenes with high yields and enantioselectivities (see scheme). The unique role of the counteranion is to stabilize an enantiomorphic conformation of the cationic Mn catalyst.

  配对：高活性和对映选择性离子对环氧化催化剂，由非手性Mn III -salen配合物和手性磷酸抗衡阴离子组成，可介导高产率和对映选择性的多种烯烃的环氧化。抗衡阴离子的独特作用是稳定阳离子Mn催化剂的对映体构象。
• Asymmetric Epoxidation of Olefins with Hydrogen Peroxide by an in Situ-Formed Manganese Complex
  作者：Wen Dai、Sensen Shang、Bo Chen、Guosong Li、Lianyue Wang、Lanhui Ren、Shuang Gao

  DOI：10.1021/jo501178k

  日期：2014.7.18

  Asymmetric epoxidation of a variety of cis, trans, terminal, and trisubstituted olefins in excellent yields (up to 94%) and enantioselectivities (>99% ee) by an in situ-formed manganese complex using H2O2 has been developed. A relationship between the hydrophobicity of the catalyst imposed by ligand and the catalytic activity has been observed. The influence of the amount and identity of the acid additive

  已经开发出了使用H 2 O 2原位形成的锰配合物，可以以优异的收率（高达94％）和对映选择性（> 99％ee）对各种顺式，反式，端基和三取代的烯烃进行不对称环氧化。已经观察到配体施加的催化剂的疏水性与催化活性之间的关系。检查了酸添加剂的量和特性的影响，并且通过使用催化量的羧酸添加剂实现了改进的对映选择性。
• A New Preparative Method of 2,2-Dimethyl-2<i>H</i>-chromenes
  作者：Yoshiyuki Kawase、Seiji Yamaguchi、Hisanori Horita、Junko Takeno、Hideaki Kameyama

  DOI：10.1246/bcsj.55.1153

  日期：1982.4

  2,2-Dimethyl-2H-chromene was prepared from salicylaldehyde and ethyl 3-methyl-2-butenoate (or ethyl α-bromoisobutyrate) in one step. This new method of preparing 2,2-dimethyl-2H-chromene was studied and applied to some 2,2-dimethyl-2H-chromene derivatives.

  2,2-二甲基-2H-色烯由水杨醛和3-甲基-2-丁烯酸乙酯（或α-溴异丁酸乙酯）一步制备。研究了这种制备2,2-二甲基-2H-色烯的新方法并将其应用于一些2,2-二甲基-2H-色烯衍生物。
• Asymmetric Epoxidation of Alkenes Catalyzed by a Porphyrin-Inspired Manganese Complex
  作者：Wen Dai、Jun Li、Guosong Li、Hua Yang、Lianyue Wang、Shuang Gao

  DOI：10.1021/ol401812h

  日期：2013.8.16

  A novel strategy for catalytic asymmetric epoxidation of a wide variety of olefins by a porphyrin-inspired chiral manganese complex using H2O2 as a terminal oxidant in excellent yield with up to greater than 99% ee has been successfully developed.
• BURRELL, GORDON;CASSIDY, FREDERICK;EVANS, JOHN M.;LIGHTOWLER, DIANE;STEMP+, J. MED. CHEM., 33,(1990) N1, C. 3023-3027
  作者：BURRELL, GORDON、CASSIDY, FREDERICK、EVANS, JOHN M.、LIGHTOWLER, DIANE、STEMP+

  DOI：——

  日期：——