2-fluoro-<α-2H>benzaldehyde | 107135-17-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-fluoro-<α-2H>benzaldehyde
• 英文别名: 2-fluoro-<α-²H>benzaldehyde；o-Fluorobenzaldehyde-α-d
• CAS: 107135-17-1
• 化学式: C₇H₅FO
• 分子量: 125.107
• InChiKey: ZWDVQMVZZYIAHO-UICOGKGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.64
• 重原子数：
  9.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-fluoro-<α-2H>benzaldehyde 在 magnesium(II) perchlorate 、 1-苯甲基-1,4-二氢烟酰胺 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Diastereoface differentiating “(net) hydride transfer” in novel 5-deazaflavins modified at pyrimidine ring

  摘要：

  In novel 5-deazaflavin models (1)-(5) where one face of the pyrimidine ring moiety is flanked, "(net) hydride transfer" from BNAH occurred at mainly C(5) on the face which aligns with the open side of the pyrimidine ring. The degree of diastereoface differentiation depends on the bulkiness of the substituent on phenyl group at N(3). The results revealed that the pyrimidine Ting moiety of flavin ring system interacts with the carbamoyl group of BNAH in the transition state of the "(net) hydride transfer" reaction. Diastereoface differentiating "(net) hydride abstraction" from the reduced 5-deazaflavin was also investigated.

  DOI：

  10.1016/s0040-4039(00)79844-3
• 作为产物：
  描述：

  邻氟苯甲酸乙酯 在 lithium aluminium deuteride 、 pyridinium chlorochromate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 2-fluoro-<α-2H>benzaldehyde
  参考文献：
  名称：

  Atropisomeric Flavoenzyme Models with a Modified Pyrimidine Ring:  Syntheses, Physical Properties, and Stereochemistry in the Reactions with NAD(P)H Analogs

  摘要：

  Optically active 5-deazaflavin derivatives (3-aryl-10-(4-tert-butylphenyl)pyrimido[4,5-b]quinoline-2,4(3H,10H)-dione) with an axial chirality at the pyrimidine ring have been synthesized, and the kinetics of enantiomerization have been measured for some of them. The absolute configurations of these compounds have been determined by X-ray crystallographic analysis and chemical reactions for the first time in atropisomeric flavoenzyme models. Enantioface-differentiating (net) hydride-transfer reactions with 1-benzyl-1,4-dihydronicotinamide (BNAH) have revealed that the selectivity of the reacting face. of the 3-[2-(hydroxymethyl)phenyl] derivative 1 changes depending on the presence or absence of Mg2+; the hydroxymethyl group of 1 exerts steric inhibition in the absence of Mg2+, whereas it facilitates the approach of BNAH. in the presence of Mg2+ Asymmetric (net) hydride-transfer reactions with chiral 1,4-dihydro-2,4-dimethyl-N-(alpha-methylbenzyl)-1-propylnicotinamide (Me(2)PNPH) predict that the most favorable intermolecular arrangement of these two molecules at the transition state is the one in which the pyrimidine ring of 1 and the carbamoyl group of Me(2)PNPH tend to face each other and the maximum overlap of their molecular planes is achieved regardless of the presence or absence of Mg2+. The arrangement mimics that of FAD and NADPH in the active site of a flavoenzyme. The present result indicates an energetically favorable overlap of the molecular planes of a flavin and an NAD(P)H coenzyme, as well. as a significant influence of functional groups from an apoenzyme in proximity to a flavin coenzyme on the stereochemistry of biological redox reactions.

  DOI：

  10.1021/jo961799t

文献信息

• Efficient synthesis of 2H &amp; 13C labeled benzaldehydes via regio-selective formylation
  作者：Sobhana B. Boga、Abdul B. Alhassan、David Hesk

  DOI：10.1016/j.tetlet.2014.06.053

  日期：2014.8

  for the synthesis of natural products and pharmaceutical drugs. Herein we report a general synthetic methodology for the synthesis of highly functionalized 2H and 13C labeled benzaldehydes in transfer of isotopic purity >99% via regio-selective formylation. Regio-selective deprotonation of substituted benzene 1 with LDA/n-BuLi at −78 °C and treatment with DMF-d7 or EtO-13CHO led to the synthesis of 2-deutero-1

  苯甲醛是合成有机化学中的重要基石，在合成天然产物和药物方面具有广泛的应用。本文中，我们报告了通过区域选择性甲酰化，以高于99％的同位素纯度转移合成高度官能化的2 H和13 C标记的苯甲醛的一般合成方法。在-78°C下用LDA / n -BuLi对取代的苯1进行区域选择性去质子化，并用DMF- d 7或EtO- 13处理CHO导致以中等至良好的产率合成了2-氘1,3-二取代的苯甲醛2/4。所描述的合成方法代表了一种简单而通用的途径，用于官能化的甲酰氘化，tri化的13 C和14 C标记的苯甲醛。
• Photodeuterierung von benzaldehyd und substituierten benzaldehyden
  作者：Albert Defoin、Rosalie Defoin-Straathann、Hans Jochen Kuhn

  DOI：10.1016/s0040-4020(01)96882-6

  日期：1984.1

  In the presence of deuterium oxide benzaldehyde () and substituted benzaldehydes likewise possessing lowest triplet states of (n,w*) character yield formyl-deuteriated benzaldehydes by fast and efficient photoreactions. Quantum yields of formation of 7-deuterio benzaldehyde in solvent acetonitrile-deuterium oxide 3:1 are 0.57 at 313 nm), 0.54 at 331 nm. 0.62 at 365 nm, and in acetone-deuterium oxide

  在氧化氘苯甲醛（）和具有最低（n，w *）特征的三重态的取代苯甲醛的存在下，通过快速和有效的光反应也可制得甲酰基-氘代苯甲醛。在溶剂乙腈-氧化氘3：1中形成7-氘代苯甲醛的量子产率在313 nm下为0.57，在331 nm下为0.54。在365 nm处为0.62，在丙酮-氘化氧化物3：1中在313 nm下为0.87。在334 nm处为0.83，在365 nm处为0.91。副产品。主要是内消旋和dl-二氢安息香和安息香。仅在很小的程度上形成。在CIDNP测量的基础上，讨论了光氘的机理。
• 1,2,4,6-Cycloheptatetraene: the key intermediate in arylcarbene interconversions and related C7H6 rearrangements
  作者：Robert J. McMahon、Christopher J. Abelt、Orville L. Chapman、Jeffery W. Johnson、Curtis L. Kreil、Jean Pierre LeRoux、Anne M. Mooring、Paul R. West

  DOI：10.1021/ja00242a034

  日期：1987.4
• Laser flash photolysis study of the effects of substituents, solvents, and quenchers on the triplet state of benzaldehydes. Hydrogen/deuterium exchange following quenching by water-d2
  作者：Helmut Gorner、Hans Jochen Kuhn

  DOI：10.1021/j100280a098

  日期：1986.10