氟化苯磺酰,3-甲酰基-2,4,6-三甲基- | 139650-07-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 氟化苯磺酰,3-甲酰基-2,4,6-三甲基-
• 英文名称: 3-Formyl-2,4,6-trimethylbenzenesulfonyl fluoride
• CAS: 139650-07-0
• 化学式: C₁₀H₁₁FO₃S
• 分子量: 230.26
• InChiKey: DZFFZMKIBQYEON-UHFFFAOYSA-N

物化性质

• 沸点：
  333.6±42.0 °C(Predicted)
• 密度：
  1.274±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  H2NO(CH2)CO-[D-Tyr(6),βAla(11),Thi(13),Nle(14)]bombesin(6-14) 、 氟化苯磺酰,3-甲酰基-2,4,6-三甲基- 以 二甲基亚砜 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  磺酰氟基义肢化合物作为潜在的18F标记剂

  摘要：

  的[亲核掺入18 F]˚F -含水条件下保持在放射性药物的开发若干优点，特别是复杂的生物药效的出现。磺酰氟可在室温下于水中制备，但尚未被检测为18 F标记的PET化学标记物的潜在手段。我们开发了一条通用路线，从乙腈，THF或叔丁基的1：1混合物中，由磺酰氯类似物制备双功能的4-甲酰基，3-甲酰基，4-马来酰亚胺基和4-氧炔基-芳基磺酰基[ 18 F]氟化物。BuOH和Cs [ 18 F] F / Cs 2 CO 3（水溶液）在室温下反应时间为15分钟。除4 - N-马来酰亚胺-苯磺酰氟（3）外，吡啶可用于选择性地降解前体而不会显着影响产率，从而简化放射性示踪剂的纯化。在[ 18 F]氟化开始时添加吡啶（1：1：0.8 t BuOH / Cs 2 CO 3（aq。） /吡啶）不会对3-甲酰基-2,4,6-三甲基苯磺酰基的收率产生负面影响[ 18 F]氟化物（2）并显着提高了4-（prop-2-ynyloxy）苯磺酰基[

  DOI：

  10.1002/chem.201103450
• 作为产物：
  描述：

  2,4,6-三甲基苯甲醛 在 吡啶 、 三聚氯氰 、 18-冠醚-6 、 发烟硫酸 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 99.0h， 生成 氟化苯磺酰,3-甲酰基-2,4,6-三甲基-
  参考文献：
  名称：

  磺酰氟基义肢化合物作为潜在的18F标记剂

  摘要：

  的[亲核掺入18 F]˚F -含水条件下保持在放射性药物的开发若干优点，特别是复杂的生物药效的出现。磺酰氟可在室温下于水中制备，但尚未被检测为18 F标记的PET化学标记物的潜在手段。我们开发了一条通用路线，从乙腈，THF或叔丁基的1：1混合物中，由磺酰氯类似物制备双功能的4-甲酰基，3-甲酰基，4-马来酰亚胺基和4-氧炔基-芳基磺酰基[ 18 F]氟化物。BuOH和Cs [ 18 F] F / Cs 2 CO 3（水溶液）在室温下反应时间为15分钟。除4 - N-马来酰亚胺-苯磺酰氟（3）外，吡啶可用于选择性地降解前体而不会显着影响产率，从而简化放射性示踪剂的纯化。在[ 18 F]氟化开始时添加吡啶（1：1：0.8 t BuOH / Cs 2 CO 3（aq。） /吡啶）不会对3-甲酰基-2,4,6-三甲基苯磺酰基的收率产生负面影响[ 18 F]氟化物（2）并显着提高了4-（prop-2-ynyloxy）苯磺酰基[

  DOI：

  10.1002/chem.201103450

文献信息

• Formylated alkylbenzenesulfonyl halide compound
  申请人：Agency of Industrial Science and Technology

  公开号：US05030752A1

  公开（公告）日：1991-07-09

  A formylated alkylbenzenesulfonyl halide compound represented by the following general formula (I): ##STR1## wherein R.sub.1 is an alkyl group having 1 to 5 carbon atoms; R.sub.2 and R.sub.3 are each a member selected from the group consisting of a hydrogen atom and alkyl groups having 1 to 5 carbon atoms; X is a halogen atom; the sulfonyl halide group is present at the ortho or para position while the formyl group at the para or ortho position relative to the group R.sub.1 when R.sub.2 and R.sub.3 are both a hydrogen atom, while the sulfonyl halide group and the formyl group are present at the para positions relative to the groups R.sub.1 and R.sub.2, respectively, when R.sub.2 is an alkyl group and R.sub.3 is a hydrogen atom, or the sulfonylhalide group and the formyl group are present at the para positions relative to the groups R.sub.1 and R.sub.2, respectively, when R.sub.2 and R.sub.3 are both an alkyl group; the compound (I) being prepared by reacting an alkylbenzene represented by the following formula (III) with carbon monoxide and a halosulfonic acid represented by the following formula (II) in the presence of an antimony halide: XSO.sub.3 H (II) ##STR2## wherein all of X in the formula (II) and R.sub.1, R.sub.2 and R.sub.3 in the formula (III) are as defined above.

  以下为通式（I）所代表的酰甲基化烷基苯磺酰卤化物化合物：##STR1## 其中，R1是具有1至5个碳原子的烷基基团；R2和R3分别是从氢原子和具有1至5个碳原子的烷基基团中选择的成员；X是卤素原子；当R2和R3均为氢原子时，磺酰卤基位于邻位或对位，而酰甲基位于对位或邻位相对于基团R1，而当R2是烷基基团而R3是氢原子时，磺酰卤基和酰甲基分别位于基团R1和R2的对位位置，而当R2和R3均为烷基基团时，磺酰卤基和酰甲基分别位于基团R1和R2的对位位置；化合物（I）通过在锑卤化物的存在下，将以下化学式（III）所代表的烷基苯和以下化学式（II）所代表的卤代磺酸和一氧化碳反应制备而成：XSO3H（II）##STR2## 其中，化学式（II）中的X以及化学式（III）中的R1、R2和R3均如上定义。
• Formylation of aromatic compounds with carbon monoxide in HSO3F-SbF5 uner atmospheric pressure
  作者：Mutsuo Tanaka、Jun Iyoda、Yoshie Souma

  DOI：10.1021/jo00035a024

  日期：1992.4

  The formylation of aromatic compounds such as benzene, toluene, xylenes, mesitylene, indan, tetralin, fluorobenzene, chlorobenzene, and bromobenzene was carried out in HSO3F-SbF5 under atmospheric CO pressure at 0-degrees-C. In HSO3F-SbF5, both formylation and sulfonation took place to give formyl and sulfonyl compounds. In the case of alkylbenzenes, including toluene, xylenes, mesitylene, and tetralin, formylalkylbenzenesulfonyl fluorides, new compounds, were obtained by a one-pot reaction as well as alkylbenzaldehydes, alkylbenzenesulfonyl fluorides, and bis(alkylphenyl) sulfones. The direct introduction of a formyl and sulfonyl group was achieved in alkylbenzenes. The reaction path of the new compounds is a two-step reaction comprised of formylation as the first step and sulfonation as the second step. The product composition was strongly dependent on the acid strength of the HSO3F-SbF5 systems. The formyl compounds became predominant with increasing acidity of the HSO3F-SbF5 system. On the other hand, only sulfonyl compounds were produced when the acidity of the HSO3F-SbF5 system was low.
• Dual Reactivity of the Formyl Cation as an Electrophile and a Broensted Acid in Superacids
  作者：Matsuo Tanaka、Masahiro Fujiwara、Hisanori Ando

  DOI：10.1021/jo00117a041

  日期：1995.6

  The nature of the formyl cation in the Gattermann-Koch formylation was studied by comparing the formylation with the acetylation and sulfonation in CF3SO3H-SbF5 and FSO3H-SbF5, respectively. The results of the kinetic studies in CF3SO3H-SbF5 showed that the formyl cation has dual reactivity as an electrophile and as a Bronsted acid. Upon comparing the formylation with the sulfonation in FSO3H-SbF5, it was found that the protonated aromatic compounds also act as Bronsted acids to produce formyl cations. Therefore, the formylation has a priority over other typical electrophilic substitutions under conditions where most of aromatic compounds are protonated because the formyl cation is reproduced close to the aromatic compounds by the protonation of CO with not only superacids but also protonated aromatic compounds.
• US5030752A
  申请人：——

  公开号：US5030752A

  公开（公告）日：1991-07-09
• US5095150A
  申请人：——

  公开号：US5095150A

  公开（公告）日：1992-03-10