6-甲基-2-苯基色满e | 5689-37-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 6-甲基-2-苯基色满e
• 英文名称: 6-methyl-2-phenylchroman
• 英文别名: 6-methylflavan；6-methyl-2-phenyl-3,4-dihydro-2H-chromene
• CAS: 5689-37-2
• 化学式: C₁₆H₁₆O
• 分子量: 224.302
• InChiKey: NPTFYGOMFVUHHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 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-甲基-2-苯基色满e 在 lead(IV) acetate 作用下， 以 苯 为溶剂， 反应 14.0h， 以9%的产率得到trans-4-acetoxy-6-methylflavan
  参考文献：
  名称：

  在苄基碳上的立体选择性：类黄酮-V 1。反式4-乙酰氨基黄酮的合成

  摘要：

  已经研究了4-取代的黄烷的一些反应。4-氯/溴衍生物在中性条件下与邻苯二甲酰亚胺和乙腈反应，导致氮转化而取代或轴向被卤素取代。相反，无论立体化学如何，4-羟基衍生物在酸性或碱性条件下反应都会导致亲核体SOCl 2，PCl 3，PCl 5，SOBr 2，PBr 3，PBr 5，乙腈和水引起轴向攻击。苄基碳正离子的中间形成。

  DOI：

  10.1016/s0040-4020(01)87374-9
• 作为产物：
  描述：

  3-(2-hydroxy-5-methylphenyl)-1-(phenyl)propan-1-one 在 potassium carbonate 、 对甲苯磺酰肼 作用下， 以 1,4-二氧六环 为溶剂， 以79%的产率得到6-甲基-2-苯基色满e
  参考文献：
  名称：

  Tosylhydrazine mediated conjugate reduction and sequential reductive coupling cyclization: synthesis of 2-arylchromans

  摘要：

  Tosylhydrazine mediated conjugate reduction of 2-hydroxyl chalcones and sequential reductive coupling cyclization is described. This is an unprecedented protocol and an extremely efficient method for a one-pot domino synthesis of 2-arylchromans in good to excellent yields from commercially available, cheap starting materials. More importantly, the two-step reactions can be easily controlled to afford dihydrochalcones or 2-arylchromans by the mole amounts of tosylhydrazine. Furthermore, the operational simplicity of the process and the high functional group tolerance are remarkable. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.08.027

文献信息

• One step synthesis of 2-alkenylchromanes via inverse electron-demand Hetero-Diels–Alder reaction of o -quinone methide with unactivated dienes
  作者：Jian Liu、Xiaoxiao Wang、Lubin Xu、Zhihui Hao、Liang Wang、Jian Xiao

  DOI：10.1016/j.tet.2016.10.027

  日期：2016.11

  The synthetically important 2-alkenylchromane derivatives were constructed in good yields under metal-free condition via inverse electron demand Hetero-Diels–Alder reaction of o-quinone methides with unactivated dienes. This strategy features mild condition, good diastereoselectivity and wide substrate scope.

  合成上重要的2-烯基苯并二氢吡喃衍生物是在无金属条件下通过反电子需求的邻醌甲基化物与未活化的二烯的杂Diels-Alder反应制备的。该策略具有条件温和，非对映选择性好和底物范围广的特点。
• Intramolecular excited-state interactions in phenol–styrene bicromophoric systems: a photochemical and photophysical study
  作者：M Consuelo Jiménez、Miguel A Miranda、Rosa Tormos

  DOI：10.1016/s0040-4020(01)01132-2

  日期：2002.1

  The intramolecular excited state interaction between phenol and styrene in a series of trans-2-cinnamylphenols bearing electron-donating substituents at the phenolic ring has been directly observed as an exciplex emission in acetonitrile. The photochemical reactivity and the relatively low fluorescence quantum yields as compared with model compounds are additional evidences for the phenol/styrene interaction

  已直接观察到一系列在酚环上带有给电子取代基的反式-2-肉桂基苯酚中苯酚和苯乙烯之间的分子内激发态相互作用，作为乙腈中的激基复合物发射。与模型化合物相比，光化学反应性和相对较低的荧光量子产率是苯酚/苯乙烯相互作用的其他证据。
• AN IMPROVED METHOD FOR SYNTHESIS OF 1-BENZOPYRANS FROM UNSATURATED ALCOHOLS AND PHENOLS USING A CATALYTIC AMOUNT OF ACIDS
  作者：Yoshio Ishino、Masatashi Mihara、Noboru Hayakawa、Tatsuya Miyata、Yoichi Kaneko、Toshiyuki Miyata

  DOI：10.1081/scc-100000537

  日期：2001.1

  1-Benzopyrans, such as chromans and chromenes, were prepared in good to excellent yields by using a catalytic amount of p-toluenesulfonic acid through intermolecular cyclization reaction of phenols with unsaturated alcohols in 1,2-dichlroroethane.
• Synthesis of Chromans via [3 + 3] Cyclocoupling of Phenols with Allylic Alcohols Using a Mo/<i>o</i>-Chloranil Catalyst System
  作者：Yoshihiko Yamamoto、Kouhei Itonaga

  DOI：10.1021/ol802800s

  日期：2009.2.5

  The combination of a molybdenum complex (CpMoCl(CO)(3) or [CpMo(CO)(3)](2)) and o-chloranil was used as a catalyst in the [3 + 3] cyclocoupling of phenols and allylic alcohols under microwave heating conditions. Substituted chromans were selectively obtained in moderate to good isolated yields.
• US4461907A
  申请人：——

  公开号：US4461907A

  公开（公告）日：1984-07-24