阿托醛 | 4432-63-7

• 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: 阿托醛
• 英文名称: 2-phenylacrolein
• 英文别名: 2-phenylpropenal；2-phenylacrylaldehyde；atropaldehyde；2-phenyl-2-propenal；alpha-phenylacrolein；2-phenylprop-2-enal
• CAS: 4432-63-7
• 化学式: C₉H₈O
• mdl: MFCD11553627
• 分子量: 132.162
• InChiKey: ZFBRJUBOJXNIQM-UHFFFAOYSA-N

物化性质

• 沸点：
  96 °C
• 密度：
  1.0406 g/cm3
• 保留指数：
  1150
• 稳定性/保质期：
  存在于主流烟气中。

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2912299000

反应信息

• 作为反应物：
  描述：

  阿托醛 在 盐酸 、 sodium chlorite 、 sodium dihydrogenphosphate 、 双氧水 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以70%的产率得到2-苯基丙烯酸
  参考文献：
  名称：

  Identification of Modified Atropaldehyde Mercapturic Acids in Rat and Human Urine after Felbamate Administration

  摘要：

  3-Carbamoyl-2-phenylpropionaldehyde has recently been proposed [Thompson et al. (1996) Chem. Res. Toxicol. 9, 1225-1229] as a potential reactive metabolite of the anti-epileptic drug felbamate. This aldehyde was found to undergo rapid elimination to generate 2-phenylpropenal and reversible cyclization to generate 4-hydroxy-5-phenyltetrahydro-1,3-oxazin-2-one at physiological pH. 2-Phenylpropenal, an alpha,beta-unsaturated aldehyde commonly termed atropaldehyde, is a potent electrophile and undergoes rapid conjugation with glutathione. We sought to demonstrate the formation of atropaldehyde in vivo through the identification of mercapturic acids in rat and human urine after felbamate administration. In this paper, we describe the identification of both the reduced (N-acetyl-S-(2-phenylpropan-3-ol)-L-cysteine) and oxidized (N-acetyl-S-(2-phenyl-3-propanoic acid)-L-cysteine) mercapturic acids of atropaldehyde in rat and human urine. The reduced species was the more abundant in human (similar to 2:1) and rat (similar to 6: 1) urine. These findings establish the possibility that atropaldehyde is formed from felbamate in vivo, undergoes glutathione conjugation, and is ultimately excreted in urine in the form of mercapturic acids. Thus, the proposed pathway of felbamate biotransformation, if confirmed in patients, could contribute to our understanding of the toxicities observed during felbamate treatment.

  DOI：

  10.1021/tx960205e
• 作为产物：
  描述：

  3-羟基-2-氨基甲酸苯丙酯 在 戴斯-马丁氧化剂 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以62%的产率得到阿托醛
  参考文献：
  名称：

  Role of Glutathione S-Transferases A1-1, M1-1, and P1-1 in the Detoxification of 2-Phenylpropenal, a Reactive Felbamate Metabolite

  摘要：

  Felbamate has proven to be an effective therapy for treating refractory epilepsy. However, felbamate therapy has been limited due to the associated reports of hepatotoxicity and aplastic anemia. Previous research from our laboratory has proposed 2-phenylpropenal as the reactive metabolite in felbamate bioactivation and identified its mercapturates in the urine of rats and patients undergoing felbamate therapy. While the reaction between 2-phenylpropenal and GSH has been shown to occur spontaneously under physiological conditions, the potential catalysis by glutathione transferases (GST) has remained unknown. The work presented here demonstrates a role for GST in the detoxification of 2-phenylpropenal. The kinetic data show that 2-phenylpropenal is a substrate for all three isoforms tested, with a k(cat)/K-m of 0.275 + 0.035 muM(-1) s(-1) for GSTM1-1, 0.164 +/- 0.005 muM(-1) s(-1) for GSTP1-1, and 0.042 +/- 0.005 muM(-1) s(-1) for GSTA1-1. Given that electrophilic substrates such as 2-propenal have been shown to inhibit GSTs, we also examined the inhibition of GSTM1-1, GSTP1-1 and GSTA1-1 by 2-phenylpropenal. The enzyme inhibition studies demonstrate that 2-phenylpropenal inhibits GSTP1-1 and GSTM1-1. The inhibition of GSTP1-1 was completely reversible upon filtration and reconstitution in buffer containing 10 mM GSH. However, 2-phenylpropenal inhibition of GSTM1-1 was irreversible under the same conditions. The irreversible inhibition of GSTM1-1 may be important in understanding the toxicities associated with felbamate. Given that 2-phenylpropenal is both a substrate and irreversible inhibitor for GSTM1-1, GSTM1-1 represents a potential target for 2-phenylpropenal haptenization in vivo, which may in turn mediate the observed idiosyncratic reactions.

  DOI：

  10.1021/tx000141e

文献信息

• C1-symmetric bisphosphine ligands and their use in the asymmetric synthesis of pregabalin
  申请人：Bao Jian

  公开号：US20050228190A1

  公开（公告）日：2005-10-13

  Materials and methods for preparing (S)-(+)-3-(aminomethyl)-5-methyl-hexanoic acid and structurally related compounds via enantioselective hydrogenation of prochiral olefins are disclosed. The methods employ novel chiral catalysts, which include C 1 -symmetric bisphosphine ligands bound to transition metals.

  通过对原生手性烯烃进行对映选择性加氢制备(S)-(+)-3-(氨甲基)-5-甲基己酸及其结构相关化合物的材料和方法已被披露。这些方法采用了新颖的手性催化剂，其中包括与过渡金属结合的C1对称双膦配体。
• Method Of Preparing Fused Ring Indeno Compounds
  申请人：Transitions Optical, Inc.

  公开号：US20150141662A1

  公开（公告）日：2015-05-21

  The present invention relates to methods of preparing fused ring indeno compounds that involves reacting together a dienophile and a lactone compound, in the presence of a catalyst, and a carboxylic acid anhydride. With some embodiments, the fused ring indeno compound is represented by the following Formula (I-A), the dienophile is represented by the following Formula (II-A), and the lactone compound is represented by the following Formula (III-A):

  本发明涉及一种制备融合环吲哚化合物的方法，涉及将双亲受体和内酯化合物在催化剂和羧酸酐的存在下反应在一起。在某些实施例中，融合环吲哚化合物由以下式(I-A)表示，双亲受体由以下式(II-A)表示，内酯化合物由以下式(III-A)表示：
• Photochromic Indeno-Fused Ring Pyran Compounds
  申请人：Transitions Optical, Inc.

  公开号：US20150141661A1

  公开（公告）日：2015-05-21

  The present invention relates to photochromic indeno-fused ring pyran compounds represented by the following Formula (I-A): The present invention also relates to photochromic dichroic compounds, such as represented by Formula (I-A), in which (i) Z 2 is a group N—R 13 in which R 13 is a group L, and (ii) optionally at least one R 1 independently for each n is selected from a group L, in which the group L independently in each case is a lengthening group that provides the photochromic compound with dichroic properties, in accordance with some embodiments. The present invention also relates to photochromic articles, such as photochromic ophthalmic articles, that include one or more photochromic compounds according to the present invention, such as represented by Formula (I-A).

  本发明涉及由以下式（I-A）表示的光致变色吲哚融合环吡喃化合物。本发明还涉及光致二向色化合物，例如由式（I-A）表示，其中（i）Z2是一个N—R13基团，其中R13是一个L基团，以及（ii）对于每个n，可选地至少选择一个R1，每种情况下独立选择自L基团，其中每种情况下L基团是一个提供光致化合物二向色性能的延伸基团，符合某些实施例。本发明还涉及光致物品，例如光致眼科物品，包括根据本发明的一个或多个光致化合物，例如由式（I-A）表示。
• 5-Benzoylamino-1,3-dioxacyclanes, the method for preparing the same and their use as PKC inhibitor
  申请人：Zen Hayley

  公开号：US20050043396A1

  公开（公告）日：2005-02-24

  The present invention discloses a series of benzoylamino-1,3-dioxacyclane compounds, of which compounds 1-21 were prepared via transacetalisation reaction between N-benzoylaminoglycol and 1,1,3,3-tetramethoxypropane; while compounds 22-48 were prepared via stereospecific acetalisation reaction between N-benzoylamino glycol and aromatic aldehyde, and if necessary, the nitro groups were reduced and further be salified with propane diacid and L-Arg or L-Lys. These compounds possess the structural type of PKC inhibitor and positive anti-inflammatory effect, and can be applied in medical fields as PKC inhibitor for corresponding therapy.

  本发明公开了一系列苯甲酰氨基-1,3-二氧杂环丁烷化合物，其中化合物1-21是通过N-苯甲酰氨基乙醇与1,1,3,3-四甲氧基丙烷之间的缩酮化反应制备的；而化合物22-48是通过N-苯甲酰氨基乙醇与芳香醛之间的立体特异性缩醛化反应制备的，如果有必要，可以将硝基还原，并进一步与丙烷二酸和L-精氨酸或L-赖氨酸成盐。这些化合物具有PKC抑制剂的结构类型和积极的抗炎效果，并且可以作为PKC抑制剂应用于医学领域的相应治疗。
• Copper-catalyzed cascade addition/cyclization: highly efficient access to phosphonylated quinoline-2,4(1H,3H)-diones
  作者：Ya-Min Li、Shi-Sheng Wang、Fuchao Yu、Yuehai Shen、Kwen-Jen Chang

  DOI：10.1039/c5ob00617a

  日期：——

  A novel Cu-catalyzed addition/cyclization cascade of o-cyanoarylacrylamide has been developed for the synthesis of various phosphonylated quinoline-2,4(1H,3H)-diones.

  已经开发了一种新型的Cu催化的o-氰基芳基丙烯酰胺的加成/环化级联反应，用于合成各种膦酰化喹诺啉-2,4(1H,3H)-二酮。