6-tert-butyl-2,2-dimethylchromene | 117610-29-4

• 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-tert-butyl-2,2-dimethylchromene
• 英文别名: 6-t-Butyl-2,2-dimethylchromene
• CAS: 117610-29-4
• 化学式: C₁₅H₂₀O
• 分子量: 216.323
• InChiKey: OTAKFLZAPUQRIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  6-tert-butyl-2,2-dimethylchromene 在 N-溴代丁二酰亚胺(NBS) 、 水 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 以18%的产率得到(3R,4S)-3-Bromo-6-tert-butyl-2,2-dimethyl-chroman-4-ol
  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 In the first series, where the benzopyran nucleus has been replaced by a pyranopyridine nucleus, the position of the nitrogen atom has been found to be critical for activity, and the most potent compounds are the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 In the second series, where the powerful electron-withdrawing cyano group of compound 1 has been replaced by alkyl and phenyl groups, the order of antihypertensive potency is ethyl, isopropyl, tert-butyl greater than propyl, cyclopentyl greater than methyl greater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：

  4-叔丁基苯酚 在 sodium hydroxide 、 苄基三甲基氢氧化铵 作用下， 以 甲醇 、 二氯甲烷 、 水 、 邻二氯苯 为溶剂， 生成 6-tert-butyl-2,2-dimethylchromene
  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 In the first series, where the benzopyran nucleus has been replaced by a pyranopyridine nucleus, the position of the nitrogen atom has been found to be critical for activity, and the most potent compounds are the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 In the second series, where the powerful electron-withdrawing cyano group of compound 1 has been replaced by alkyl and phenyl groups, the order of antihypertensive potency is ethyl, isopropyl, tert-butyl greater than propyl, cyclopentyl greater than methyl greater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

文献信息

• Asymmetric Epoxidation of Chromenes Using Manganese(III) Complexes with Novel Chiral Salen-like Schiff Base Ligands
  作者：Longhai Chen、Jian Wei、Ning Tang、Feixiang Cheng

  DOI：10.1007/s10562-012-0787-3

  日期：2012.4

  Three novel chiral salen-like schiff base ligands and their Mn(III) complexes containing different amino acid unit have been synthesized and characterized. Asymmetric epoxidation reactions show these complexes are effective catalysts for the chromenes with buffer NaOCl as terminal oxidant and pyridine N-oxide as co-catalyst in the presence of ionic liquid. Good-to -excellent enantioselectivity and acceptable

  合成并表征了三种新型手性类沙伦希夫碱配体及其含有不同氨基酸单元的 Mn(III) 配合物。不对称环氧化反应表明，这些配合物是在离子液体存在下以缓冲液 NaOCl 作为末端氧化剂和吡啶 N-氧化物作为助催化剂的色烯的有效催化剂。在最佳反应条件下可以获得良好到优异的对映选择性和可接受的产率。在这些催化性能中，催化剂 4c 为 6-氯-2,2-二甲基色烯提供了最高的 ee (95%)。此外，比较催化剂4c与其他两种催化剂4a和4b的对映选择性，积极的实验结果表明配体的空间效应在不对称催化中起重要作用。
• Manganese(III) complexes of novel chiral unsymmetrical BINOL-Salen ligands: Synthesis, characterization, and application in asymmetric epoxidation of olefins
  作者：Longhai Chen、Feixiang Cheng、Lei Jia、Lei Wang、Jian Wei、Jinfeng Zhang、Lihui Yao、Ning Tang、Jincai Wu

  DOI：10.1016/j.apcata.2011.12.001

  日期：2012.2

  Several chiral unsymmetrical and C2-symmetric Mn(III)-BINOL-Salen complexes have been designed, synthesized and applied to the asymmetric epoxidation of non-functionalized alkenes. Experimental results show these complexes are effective in the catalytic asymmetric epoxidation of alkenes. The catalyst 4c exhibited better enantioselectivity and reactivity than the catalysts 4b and 4a due to the steric

  几种手性不对称和C 2对称的Mn（III）-BINOL-Salen配合物已被设计，合成并应用于非官能化烯烃的不对称环氧化。实验结果表明，这些配合物可有效地催化烯烃的不对称环氧化。由于配体的空间效应，催化剂4c表现出比催化剂4b和4a更好的对映选择性和反应性。为了理解催化剂中两个不同手性中心的协同作用，已经研究了催化剂6a。通过比较使用4c和6a获得的对映选择性分别的积极实验结果证明，在二氨基环己烷衍生的催化剂中的手性立体中心在当前的对映选择性环氧化中起着重要作用。此外，通过4c和7a显示的对映选择性的比较进一步证明了通过空间因子和手性中心在催化剂中的协同作用的显着影响。
• Catalytic enantioselective synthesis of flavanones and chromanones
  申请人：Scheidt Karl

  公开号：US20110117649A1

  公开（公告）日：2011-05-19

  Various chromanone, flavanone and abyssinone compounds as can be prepared enantioselectively using a chiral thiourea catalyst.

  使用手性硫脲催化剂可以对各种色酮、黄酮和阿比西农化合物进行对映选择性制备。
• Pharmacologically active benzopyranes
  申请人：BEECHAM GROUP PLC

  公开号：EP0250077A2

  公开（公告）日：1987-12-23

  Compounds of formula (I) and pharmaceutically accetable salts thereof: wherein: Y is N or (when R3 is hydroxy, C1-6 alkoxy or C1-7 acyloxy) CH; one of R1 and R2 is hydrogen or C1-4 alkyl and the other is C1-4 alkyl or R1 and R2 together are C2-s-polymethylene; R3 is hydrogen, hydroxy, C1-6 alkoxy or C1-7 acyloxy; R4 is a C3-8 cycloalkyl group or a C1-6 alkyl group optionally substituted by a group R7 which is hydroxy, C1-6 alkoxy, amino optionally substituted by one or two C1-6 alkyl groups; C1-7 alkanoylamino, C3-8 cycloalkyloxy, C3-8 cycloalkylamino, or 1,3-dioxo-2-isoindoline; when Y is N, R5 is hydrogen, C1-6 alkyl optionally substituted by halogen, hydroxy, C1-6 alkoxy, C1-6 alkoxycarbonyl, carboxy or amino optionally substituted by one or two independent C1-6 alkyl groups, or C2-6 alkenyl, amino optionally substituted by a C1-6 alkyl, C3-a cycloalkyl or C1-6 alkenyl group or by a C1-6 alkanoyl group optionally substituted by up to three halo atoms, by a phenyl group optionally substituted by C1-6 alkyl, C1-6 alkoxy or halogen, or aryl or heteroaryl, either being optionally substituted by one or more groups or atoms selected from the class of C1-6 alkyl, C1-6 alkoxy, hydroxy, halogen, trifluoromethyl, nitro, cyano, C1-12 carboxylic acyl, or amino or aminocarbonyl optionally substituted by one or two C1-6 alkyl groups and R6 is hydrogen or C1-6 alkyl, or R5 and R6 together are -CH2-(CH2)n-Z-(CH2)m- wherein m and n are 0 to 2 such that m + n is 1 or 2 and Z is CH2, O, S or NR wherein R is hydrogen, C1-9 alkyl, C2-7 alkanoyl, phenyl C1-4-alkyl, naphthylcarbonyl, phenylcarbonyl or benzyl-carbonyl optionally substituted in the phenyl or naphthyl ring by one or two of C1-6 alkyl, C1-6 alkoxy or halogen; mono- or bi-cyclic- heteroarylcarbonyl; when Y is CH, R5 is NR8R9 wherein R8 and R9 are independently C1-6 alkyl, R8 is hydrogen and R9 is C1-6 alkyl or R8 and R9 together are C4-5 polymethylene; or R6 and R8 together are -(CH2)p- wherein p is 2 or 3, and R9 is hydrogen or C1-6 alkyl; or R5 is CH2R10 wherein R10 is hydrogen or C1-5 alkyl; or R6 and R10 are -(CH2)q- wherein q is 2 or 3; X is oxygen or sulphur; or R5, R6, X and Y (when N) together are tetrahydroisoquinolinone ortetrahydroisoquinolinthione, optionally substituted in the phenyl ring as defined for R above; the nitrogen-containing group is in the 4-position being trans to the R3 group when R3 is hydroxy, C1-6 alkoxy or C1-7 acyloxy; having K+ channel activator activity, processes for their preparation and their use as pharmaceuticals.

  式 (I) 的化合物及其可药用盐： 其中 Y 是 N 或（当 R3 是羟基、C1-6 烷氧基或 C1-7 乙酰氧基时）CH； R1 和 R2 中的一个是氢或 C1-4 烷基，另一个是 C1-4 烷基，或 R1 和 R2 合在一起是 C2-s 聚亚甲基； R3 是氢、羟基、C1-6 烷氧基或 C1-7 丙烯酸氧基； R4 是 C3-8 环烷基或任选被一个基团 R7 取代的 C1-6 烷基，该基团是羟基、C1-6 烷氧基、任选被一个或两个 C1-6 烷基取代的氨基、C1-7 烷酰氨基、C3-8 环烷氧基、C3-8 环烷基氨基或 1,3-二氧代-2-异吲哚啉； 当 Y 是 N 时，R5 是氢、任选被卤素、羟基、C1-6 烷氧基、C1-6 烷氧羰基、羧基或任选被一个或两个独立 C1-6 烷基取代的氨基取代的 C1-6 烷基，或 C2-6 烯基、任选被 C1-6 烷基取代的氨基、C3-a环烷基或C1-6烯基，或被最多三个卤原子任选取代的C1-6烷酰基，或被C1-6烷基、C1-6烷氧基或卤素任选取代的苯基，或芳基或杂芳基，其中任一芳基或杂芳基被一个或多个选自C1-6烷基类的基团或原子任选取代、C1-6烷氧基、羟基、卤素、三氟甲基、硝基、氰基、C1-12 羧酰基或氨基或氨基羰基中任选被一个或两个 C1-6 烷基取代，且 R6 为氢或 C1-6 烷基，或 R5 和 R6 合在一起为-CH2-( )n-Z-( )m-，其中 m 和 n 为 0 至 2，使得 m + n 为 1 或 2，且 Z 为 、O、S 或 NR，其中 R 是氢、C1-9 烷基、C2-7 烷酰基、苯基 C1-4-烷基、萘基羰基、苯基羰基或苄基羰基，可选择在苯基或萘基环上被一个或两个 C1-6 烷基、C1-6 烷氧基或卤素取代；单环或双环杂芳基羰基； 当 Y 是 CH 时，R5 是 NR8R9，其中 R8 和 R9 独立地是 C1-6 烷基，R8 是氢，R9 是 C1-6 烷基，或 R8 和 R9 一起是 C4-5 聚亚甲基；或 R6 和 R8 一起是-( )p-，其中 p 是 2 或 3，R9 是氢或 C1-6 烷基；或 R5 是 R10，其中 R10 是氢或 C1-5 烷基；或 R6 和 R10 是-( )q-，其中 q 是 2 或 3； X 是氧或硫；或 R5、R6、X 和 Y（当为 N 时）一起是四氢异喹啉酮或四氢异喹啉乙硫酮，如上文对 R 所定义，可选择被取代的苯基环； 当 R3 为羟基、C1-6 烷氧基或 C1-7 乙酰氧基时，含氮基团位于反式至 R3 基团的 4 位；具有 K+通道激活剂活性，其制备工艺及其作为药物的用途。
• 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：——