3-(2-bromoethyl)chroman-4-one | 1610423-75-0

• 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-bromoethyl)chroman-4-one
• 英文别名: 3-(2-Bromoethyl)-2,3-dihydrochromen-4-one
• CAS: 1610423-75-0
• 化学式: C₁₁H₁₁BrO₂
• 分子量: 255.111
• InChiKey: QCXNSXZEMZESQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(2-bromoethyl)chroman-4-one 在 3-mesityl-5,6,7,8-tetrahydro-4H-cyclohepta[d]thiazol-3-ium perchlorate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.5h， 以92%的产率得到spiro[chromane-3,1’-cyclopropan]-4-one
  参考文献：
  名称：

  N-Heterocyclic Carbene Catalyzed Intramolecular Acylation of Allylic Electrophiles

  摘要：

  The N-heterocyclic carbene (NHC) catalyzed addition reaction has been well documented recently; however, the NHC-catalyzed substitution reaction especially the S(N)2' type reaction remains a challenge. As one of the most fundamental reaction types in organic chemistry, the S(N)2' reaction catalyzed by NHC would be a powerful tool in organic synthesis. Therefore, the first NHC-catalyzed intramolecular S(N)2' substitution reaction of aldehyde with allylic electrophiles has been developed. A variety of alpha,beta-unsaturated chromanones were obtained under a domino S(N)2' reaction and isomerization. Mechanistic experiments were conducted to confirm the nature of this S(N)2' reaction.

  DOI：

  10.1021/ol501046p
• 作为产物：
  描述：

  在 sodium hydroxide 、 四溴化碳 、 三苯基膦 作用下， 以 甲醇 为溶剂， 以46%的产率得到3-(2-bromoethyl)chroman-4-one
  参考文献：
  名称：

  N-Heterocyclic Carbene Catalyzed Intramolecular Acylation of Allylic Electrophiles

  摘要：

  The N-heterocyclic carbene (NHC) catalyzed addition reaction has been well documented recently; however, the NHC-catalyzed substitution reaction especially the S(N)2' type reaction remains a challenge. As one of the most fundamental reaction types in organic chemistry, the S(N)2' reaction catalyzed by NHC would be a powerful tool in organic synthesis. Therefore, the first NHC-catalyzed intramolecular S(N)2' substitution reaction of aldehyde with allylic electrophiles has been developed. A variety of alpha,beta-unsaturated chromanones were obtained under a domino S(N)2' reaction and isomerization. Mechanistic experiments were conducted to confirm the nature of this S(N)2' reaction.

  DOI：

  10.1021/ol501046p

文献信息

• HYDROGEN PEROXIDE SENSORS BASED UPON PHOTO-INDUCED ELECTRON TRANSFER
  申请人：He Huarui

  公开号：US20120183984A1

  公开（公告）日：2012-07-19

  The invention provides compounds of formula I F-L-Q (I) where F comprises a fluorophore capable of absorbing energy at an excitation wavelength and, in the absence of a quencher, emitting energy at an emission wavelength, which is different than the excitation wavelength; Q comprises a quencher; L comprises a linker moiety having two ends, one end being covalently bound to F and the other end being covalently bound to Q. The compounds are capable of undergoing a reversible reaction (1), provided below: (1) where Q + is an oxidized form of Q representing the absence of a quencher, Ox comprises an oxidizing agent, which is capable of oxidizing Q to its oxidized form Q, and Red comprises a reducing agent, which is capable of converting Q back to its reduced form Q. The compounds can undergo photo-induced electron transfer when irradiated with energy and when Q exists in its oxidized form, Q + . The invention also provides methods of detecting and determining the presence of analytes and/or hydrogen peroxide in a sample, as well as a substrate that comprises the compound of formula I.