2,2-dimethyl-6-fluorochromene oxide | 380498-97-5

• 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-fluorochromene oxide
• 英文别名: (3R,4R)-2,2-dimethyl-6-fluorochromene oxide；(1aR,7bR)-6-fluoro-2,2-dimethyl-1a,7b-dihydrooxireno[2,3-c]chromene
• CAS: 380498-97-5
• 化学式: C₁₁H₁₁FO₂
• 分子量: 194.206
• InChiKey: HOVYBIAWIZUPDL-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-6-fluorochromene oxide 在 氨 作用下， 以 乙醇 为溶剂， 生成 (3R,4S)-4-Amino-6-fluoro-2,2-dimethyl-chroman-3-ol
  参考文献：
  名称：

  新型反式-4-（取代的苯甲酰胺基）-3,4-二氢-2H-苯并[b]-吡喃-3-醇衍生物的合成作为潜在的具有独特结合特征的抗惊厥药。

  摘要：

  DOI：

  10.1021/jm960535w
• 作为产物：
  描述：

  6-氟-2,3-二氢-2,2-二甲基色烯-4-酮 在 sodium hypochlorite 、 sodium tetrahydroborate 、 disodium hydrogenphosphate 、 R,R-Jacobsen's catalyst 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 23.0h， 生成 2,2-dimethyl-6-fluorochromene oxide
  参考文献：
  名称：

  Synthesis and Activity of Novel and Selective I_Ks-Channel Blockers

  摘要：

  Since the discovery of the I-Ks-potassium channel as the slowly activating component of the delayed rectifier current (I-k) in cardiac tissue, the search for blockers of this current has been intense. During the screening of K-ATP-channel openers of the chromanol type we found that chromanol 293B was able to block I-Ks. Chromanol 293B is a sulfonamide analogue of the K-ATP-channel openers but had no activity on this target. Experiments were initiated to improve the activity and properties based on this lead compound. As a screening model we used Xenopus oocytes injected with human minK (KCNE1). Variations of the aromatic substituent and the sulfonamide group were prepared, and their activity was evaluated. We found that the greatest influence on activity was found in the aromatic substituents. The most active compounds were alkoxy substituted. We chose HMR1556 ((3R, 4S)-(+)-N-[-3-hydroxy-2,2-dimethyl-6-(4,4,4-trifluorobutoxy)chroman-4-yl]-N-methyl-ethanesulfonamide) 10a for development as an antiarrhythmic drug. The absolute configuration, resulting from an X-ray single-crystal structure analysis, was determined.

  DOI：

  10.1021/jm0109255

文献信息

• Multivariate Metal–Organic Frameworks as Multifunctional Heterogeneous Asymmetric Catalysts for Sequential Reactions
  作者：Qingchun Xia、Zijian Li、Chunxia Tan、Yan Liu、Wei Gong、Yong Cui

  DOI：10.1021/jacs.7b03113

  日期：2017.6.21

  The search for versatile heterogeneous catalysts with multiple active sites for broad asymmetric transformations has long been of great interest, but it remains a formidable synthetic challenge. Here we demonstrate that multivariate metal-organic frameworks (MTV-MOFs) can be used as an excellent platform to engineer heterogeneous catalysts featuring multiple and cooperative active sites. An isostructural

  长期以来，人们对寻找具有多个活性位点的多功能多相催化剂进行广泛的不对称转化一直很感兴趣，但它仍然是一个艰巨的合成挑战。在这里，我们证明了多元金属有机框架 (MTV-MOF) 可用作设计具有多个协同活性位点的多相催化剂的绝佳平台。构建了包含多达三种不同手性金属盐催化剂的 2 倍互穿 MTV-MOF 的同构系列，并将其用作各种不对称顺序烯烃环氧化/环氧化物开环反应的高效且可回收的多相催化剂。框架的相互渗透使金属盐单元彼此相邻，允许协同激活，这导致在单个部分的总和上提高效率和对映选择性。在 MTV-MOF 中操纵分子催化剂可以控制活性和选择性的事实将有助于设计用于对映选择性过程的新型多功能材料。
• Heterogenisation of ketonecatalysts within mesoporous supports for asymmetric epoxidation
  作者：Lynda J. Brown、Richard C. D. Brown、Robert Raja

  DOI：10.1039/c2ra21837b

  日期：——

  The synthesis of the first mesoporous silica (150 Å) anchored carbohydrate-derived chiral ketone is described. This new heterogeneous catalyst has been shown to be effective in the asymmetric epoxidation of olefins by oxone. The heterogeneous ketone catalyst has comparable activity to that of its homogeneous counterpart and returned enantioselectivities up to 90% e.e.

  第一介孔的合成 硅石描述了（150Å）锚定的碳水化合物衍生的手性酮。这种新的非均相催化剂已被证明对烯烃的不对称环氧化有效。酮。非均相酮催化剂具有与其均相对应物相当的活性，返回的对映选择性高达90％ee。
• Studies of Substituent Effect on Asymmetric Epoxidation of Chromenes by Chiral Dioxirane
  作者：O. Andrea Wong、Yian Shi

  DOI：10.1021/jo0604179

  日期：2006.5.1

  A series of 6- and 8-substituted chromenes has been investigated for asymmetric epoxidation using chiral ketone catalysts. Up to 93% ee was achieved. Higher ee's are obtained when substrates are substituted at the 6- position. The enhanced enantioselectivity is likely due to the beneficial interaction between the 6-substituent of the substrate and the N-aryl or alkyl group of the ketone catalyst.
• Synthesis and Activity of Novel and Selective I_Ks-Channel Blockers
  作者：Uwe Gerlach、Joachim Brendel、Hans-Jochen Lang、Erich F. Paulus、Klaus Weidmann、Andrea Brüggemann、Andreas E. Busch、Hartmut Suessbrich、Markus Bleich、Rainer Greger

  DOI：10.1021/jm0109255

  日期：2001.11.1

  Since the discovery of the I-Ks-potassium channel as the slowly activating component of the delayed rectifier current (I-k) in cardiac tissue, the search for blockers of this current has been intense. During the screening of K-ATP-channel openers of the chromanol type we found that chromanol 293B was able to block I-Ks. Chromanol 293B is a sulfonamide analogue of the K-ATP-channel openers but had no activity on this target. Experiments were initiated to improve the activity and properties based on this lead compound. As a screening model we used Xenopus oocytes injected with human minK (KCNE1). Variations of the aromatic substituent and the sulfonamide group were prepared, and their activity was evaluated. We found that the greatest influence on activity was found in the aromatic substituents. The most active compounds were alkoxy substituted. We chose HMR1556 ((3R, 4S)-(+)-N-[-3-hydroxy-2,2-dimethyl-6-(4,4,4-trifluorobutoxy)chroman-4-yl]-N-methyl-ethanesulfonamide) 10a for development as an antiarrhythmic drug. The absolute configuration, resulting from an X-ray single-crystal structure analysis, was determined.
• Synthesis of Novel <i>trans</i>-4-(Substituted-benzamido)-3,4-dihydro-2<i>H</i>-benzo[<i>b</i>]pyran-3-ol Derivatives as Potential Anticonvulsant Agents with a Distinctive Binding Profile
  作者：Wai N. Chan、John M. Evans、Michael S. Hadley、Hugh J. Herdon、Jeffrey C. Jerman、Helen K. A. Morgan、Tania O. Stean、Mervyn Thompson、Neil Upton、Antonio K. Vong

  DOI：10.1021/jm960535w

  日期：1996.1.1