dioxolanne de l'acetyl-3 methoxy-6 benzaldehyde | 81224-35-3

• 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: dioxolanne de l'acetyl-3 methoxy-6 benzaldehyde
• 英文别名: 5-(1,1-Ethylenedioxy-ethyl)-2-methoxy benzaldehyde；2-methoxy-5-(2-methyl-1,3-dioxolan-2-yl)benzaldehyde
• CAS: 81224-35-3
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: GDLHBOJTFUJFKI-UHFFFAOYSA-N

物化性质

• 熔点：
  173 °C(Solv: isopropyl ether (108-20-3))
• 沸点：
  353.9±42.0 °C(Predicted)
• 密度：
  1.175±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dioxolanne de l'acetyl-3 methoxy-6 benzaldehyde 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 生成 5-乙酰基-2-甲氧基苯甲醛
  参考文献：
  名称：

  Substituent control of intramolecular hydrogen bonding in formyl-protonated o-anisaldehydes: a stable ion and semiempirical MO investigation

  摘要：

  o-Anisaldehyde and its 5-Br, 5-F, 5-CF3, 5-CN, 5-NO2, and 5-COMe derivatives are protonated at the formyl group in 1:1 SbF5-FSO3H/SO2 (or SO2ClF) to give persistent carboxonium ions as mixtures of Z and E geometrical isomers. The cyano, nitro, and acetyl substituents are also protonated, leading to dications and additional geometrical isomers in the nitro and acetyl cases. The carboxonium ions are predominantly in the Z,syn configuration, but with increased amounts of the E,anti configuration with increased electron withdrawal by the substituents. With 5-NO2H+, E isomers become more abundant than Z. The formyl protonated 2-(trifluoromethoxy)benzaldehyde shows a strong preference for the E configuration. The preference for the Z,syn form is attributed to intramolecular hydrogen bonding that becomes less favorable as electron density is withdrawn from the methoxyl oxygen. The log Z/E values correlate with differences in energy content of the isomers predicted in AM1 calculations, and the chemical shift of the hydroxyl proton of the carboxonium group correlates well with predicted charge on the proton.

  DOI：

  10.1021/jo00058a018
• 作为产物：
  描述：

  1-(3-溴-4-甲氧基苯基)乙烯酮 在 正丁基锂 、 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 2.45h， 生成 dioxolanne de l'acetyl-3 methoxy-6 benzaldehyde
  参考文献：
  名称：

  Substituent control of intramolecular hydrogen bonding in formyl-protonated o-anisaldehydes: a stable ion and semiempirical MO investigation

  摘要：

  o-Anisaldehyde and its 5-Br, 5-F, 5-CF3, 5-CN, 5-NO2, and 5-COMe derivatives are protonated at the formyl group in 1:1 SbF5-FSO3H/SO2 (or SO2ClF) to give persistent carboxonium ions as mixtures of Z and E geometrical isomers. The cyano, nitro, and acetyl substituents are also protonated, leading to dications and additional geometrical isomers in the nitro and acetyl cases. The carboxonium ions are predominantly in the Z,syn configuration, but with increased amounts of the E,anti configuration with increased electron withdrawal by the substituents. With 5-NO2H+, E isomers become more abundant than Z. The formyl protonated 2-(trifluoromethoxy)benzaldehyde shows a strong preference for the E configuration. The preference for the Z,syn form is attributed to intramolecular hydrogen bonding that becomes less favorable as electron density is withdrawn from the methoxyl oxygen. The log Z/E values correlate with differences in energy content of the isomers predicted in AM1 calculations, and the chemical shift of the hydroxyl proton of the carboxonium group correlates well with predicted charge on the proton.

  DOI：

  10.1021/jo00058a018

文献信息

• New cinnamoyl-cinnamic acid derivative, and its use as pharmaceutical
  申请人：Societe de Recherches Industrielles (S.O.R.I.)

  公开号：US04421927A1

  公开（公告）日：1983-12-20

  The present invention relates to a new cinnamoyl-cinnamic acid derivative selected from the group constituted by: (i) the m-cinnamoyl-cinnamic acid derivatives of formula ##STR1## in which: X.sub.o,X.sub.1,X.sub.2,X.sub.3,X.sub.4, which are identical or different, each represent an atom of hydrogen, a halogen, a lower alkyl group, a lower alkoxy group, the group NRR' (where R and R' identical or different, each represent an atom of hydrogen or a lower alkyl group), the group NO.sub.2, CF.sub.3 or OH; R.sub.1 represents an atom of hydrogen or a lower alkyl group; R.sub.2 represents an atom of hydrogen or the methyl group; Y represents a group OH, OR.sub.3 (where R.sub.3 is a lower alkyl group), NRR' (where R and R' are defined as hereinabove) or the group O(CH.sub.2).sub.n NR.sub.4 R.sub.5 (where n is an integer of value 1 to 5--and preferably 2 or 3)--; and R.sub.4 and R.sub.5, identical or different, each represent an atom of hydrogen, a lower alkyl group and may form with the nitrogen atom to which they are bonded a heterocyclic group of 5 to 7 vertices capable of being substituted and of comprising one or more other heteroatoms such as N and O); (ii) their geometrical isomers; and (iii) their salts. It also relates to its method of preparation and its use as pharmaceutical.

  本发明涉及一种新的肉桂酰肉桂酸衍生物，所述衍生物选自由以下组成的群体：（i）式##STR1##中的m-肉桂酰肉桂酸衍生物，其中：Xo，X1，X2，X3，X4相同或不同，分别表示氢原子，卤素，低烷基，低烷氧基，NRR'（其中R和R'相同或不同，分别表示氢原子或低烷基），NO2，CF3或OH基团；R1表示氢原子或低烷基；R2表示氢原子或甲基基团；Y表示OH基团，OR3（其中R3为低烷基），NRR'（其中R和R'如上所述定义）或O（CH2）nNR4R5基团（其中n为1至5的整数，优选为2或3）；R4和R5相同或不同，分别表示氢原子，低烷基，并且可以与它们连接的氮原子形成5至7个顶点的杂环基团，该杂环基团可被取代并包含一个或多个其他杂原子，如N和O）；（ii）它们的几何异构体；（iii）它们的盐。它还涉及其制备方法和作为药物的用途。
• Dérivé d'acide cinnamoyl-cinnamique, son procédé de préparation et son application en thérapeutique
  申请人：SOCIETE DE RECHERCHES INDUSTRIELLES S.O.R.I. Société anonyme dite:

  公开号：EP0051514A1

  公开（公告）日：1982-05-12

  La présente invention concerne un nouveau dérivé d'acide cinnamoyl-cinnamique choisi parmi l'ensemble constitué par (i) les dérivés d'acide m-cinnamoyl-cinnamique de formule dans laquelle: - X0, X1, X2, X3, X4, identiques ou différents, représentent chacun l'atome d'hydrogène, un halogène, un groupe alkyle inférieur, un groupe alkoxy inférieur, le groupe NRR' (où R et R', identiques ou différents, représentent chacun l'atome d'hydrogène ou un groupe alkyle inférieur), le groupe N02, CF3 ou OH; - R1 représente l'atome d'hydrogène ou un groupe alkyle inférieur ; - R2 représente l'atome d'hydrogène ou le groupe méthyle ; - Y représente un groupe OH, OR3 (où R3 est un groupe alkyle inférieur), NRR' (où R et R' sont définis comme ci-dessus) ou le groupe O(CH2)nNR4R5 (où n est un nombre entier ayant pour valeur 1 à 5 - et de préférence 2 ou 3 - ; et R4 et Rs, identiques ou différents, représentent chacun l'atome d'hydrogène, un groupe alkyle inférieur et peuvent former avec l'atome d'azote auquel ils sont liés un groupe hétérocyclique de 5 à 7 sommes susceptible d'être substitué et de comporter un ou plusieurs autres hétéroatomes tels que N et 0) ; (ii) leurs isomères géométriques ; et (iii) leurs sels. Elle concerne également son procédé de préparation et son application en thérapeutique.

  本发明涉及一种新的肉桂酰肉桂酸衍生物，该衍生物选自以下组别 (i) 式中的间肉桂酰肉桂酸衍生物 其中 - X0、X1、X2、X3 和 X4(可以相同或不同)各自代表氢原子、卤素、低级烷基、低级烷氧基、基团 NRR'(其中 R 和 R'可以相同或不同，各自代表氢原子或低级烷基)、基团 N02、CF3 或 OH； - R1 代表氢原子或低级烷基； - R2 代表氢原子或甲基； - Y 代表基团 OH、OR3（其中 R3 为低级烷基）、NRR'（其中 R 和 R'的定义同上）或基团 O(CH2)nNR4R5（其中 n 为 1 至 5 的整数，最好为 2 或 3）；R4和Rs可以相同或不同，各自代表一个氢原子或一个低级烷基，与它们所键合的氮原子一起可形成一个5-7元杂环基团，该基团可以被取代，并含有一个或多个其他杂原子，如N和0）； (ii) 它们的几何异构体；以及 (iii) 它们的盐类。 它还涉及其制备工艺和治疗应用。
• Kim, Phieo Ta; Guillard, Roger; Samreth, Soth, Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 1373 - 1377
  作者：Kim, Phieo Ta、Guillard, Roger、Samreth, Soth、Sornay, Roland

  DOI：——

  日期：——
• KIM, PHIEO, TA;GUILARD, R.;SAMRETH, S.;SORNAY, R., J. HETEROCYCL. CHEM., 1981, 18, N 7, 1373-1377
  作者：KIM, PHIEO, TA、GUILARD, R.、SAMRETH, S.、SORNAY, R.

  DOI：——

  日期：——
• Substituent control of intramolecular hydrogen bonding in formyl-protonated o-anisaldehydes: a stable ion and semiempirical MO investigation
  作者：Kenneth K. Laali、Gerald F. Koser、Sundar Subramanyam、David A. Forsyth

  DOI：10.1021/jo00058a018

  日期：1993.3

  o-Anisaldehyde and its 5-Br, 5-F, 5-CF3, 5-CN, 5-NO2, and 5-COMe derivatives are protonated at the formyl group in 1:1 SbF5-FSO3H/SO2 (or SO2ClF) to give persistent carboxonium ions as mixtures of Z and E geometrical isomers. The cyano, nitro, and acetyl substituents are also protonated, leading to dications and additional geometrical isomers in the nitro and acetyl cases. The carboxonium ions are predominantly in the Z,syn configuration, but with increased amounts of the E,anti configuration with increased electron withdrawal by the substituents. With 5-NO2H+, E isomers become more abundant than Z. The formyl protonated 2-(trifluoromethoxy)benzaldehyde shows a strong preference for the E configuration. The preference for the Z,syn form is attributed to intramolecular hydrogen bonding that becomes less favorable as electron density is withdrawn from the methoxyl oxygen. The log Z/E values correlate with differences in energy content of the isomers predicted in AM1 calculations, and the chemical shift of the hydroxyl proton of the carboxonium group correlates well with predicted charge on the proton.