Styrylglyoxal | 6784-05-0

• 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: Styrylglyoxal
• 英文别名: 2-oxo-4-phenylbut-3-enal
• CAS: 6784-05-0
• 化学式: C₁₀H₈O₂
• 分子量: 160.172
• InChiKey: PBPWOWKXFXYSAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Styrylglyoxal 在 hydroxide 作用下， 生成 3-Hydroxy-5-oxo-2-styrylcyclopent-1-en-heptancarbonsaeure
  参考文献：
  名称：

  15-脱氢前列腺素E 1的全合成

  摘要：

  DOI：

  10.1016/s0040-4039(01)87960-0
• 作为产物：
  描述：

  苄叉丙酮 在 selenium(IV) oxide 作用下， 生成 Styrylglyoxal
  参考文献：
  名称：

  Epoxydiazo ketones. Synthesis and reactions

  摘要：

  DOI：

  10.1021/jo00912a012

文献信息

• Process for the production of 2.beta.-formyl 3.alpha.-protected
  申请人：G. D. Searle & Co.

  公开号：US03932467A1

  公开（公告）日：1976-01-13

  2-Formyl-3-protected hydroxy-5-oxocyclopent-1-eneheptanoic acid and its esters are stereoselectively reduced to the corresponding 2.beta.-formyl-3.alpha.-protected hydroxy-5-oxocyclopentane-1.alpha.-heptanoic acid and esters with chromous sulfate. The compounds so produced are useful as intermediates to PGE.sub.1 and its esters, which compounds exhibit hypotensive and smooth muscle-stimulating properties.

  2-甲酰基-3-保护羟基-5-酮基环戊-1-烯庚酸及其酯类，经铬酸铬选择性还原为相应的2-β-甲酰基-3-α-保护羟基-5-酮基环戊烷-1-α-庚酸和酯类。所得化合物可用作PGE.sub.1及其酯类的中间体，这些化合物具有降压和平滑肌刺激作用。
• Prostaglandin intermediates and optically active isomers thereof
  申请人：G. D. Searle & Co.

  公开号：US03980700A1

  公开（公告）日：1976-09-14

  The condensation of dimethyl 3-oxoundecane-1,11-dioate with styrylglyoxal affords 14-phenyl-9,12-dioxo-11-hydroxytetradec-13-enoic acid, which is cyclized to afford 3-hydroxy-5-oxo-2-styrylcyclopent-1-eneheptanoic acid. Hydroxylation of the styryl double bond affords the corresponding 2-(.alpha.,.beta.-dihydroxyphenethyl) derivative. Resolution of the racemic 2-styryl-3-hydroxy compounds with either (-) or (+)-O-methylmandelyl chloride yields the optically active isomers which are separated chromatographically. The instant compounds are useful as anti-microbial, anti-fungal and hypotensive agents, as prostaglandin (PGE.sub.2) antagonists and also as intermediates to prostanoic acid derivatives and their optically active isomers which exhibit anti-microbial, pepsin-inhibitory, hypotensive and smooth muscle-contracting properties.

  二甲基3-氧代十一酸-1,11-二酯与苯乙烯基乙二醛缩合生成14-苯基-9,12-二氧代-11-羟基四十四烯酸，经环化反应得到3-羟基-5-氧代-2-苯乙烯基环戊-1-烯庚酸。对苯乙烯基双键进行羟化反应，得到相应的2-（α，β-双羟基苯乙基）衍生物。用（-）或（+）-O-甲基曼德酰氯分离外消旋的2-苯乙烯基-3-羟基化合物，得到对映体，通过色谱分离。这些化合物可用作抗微生物、抗真菌和降压剂，作为前列腺素（PGE.sub.2）拮抗剂，也可用作前列酸衍生物及其对映体的中间体，这些对映体具有抗微生物、胃蛋白酶抑制、降压和平滑肌收缩特性。
• Peptide-Catalyzed Highly Asymmetric Cross-Aldol Reaction of Aldehydes to Biomimetically Synthesize 1,4-Dicarbonyls
  作者：Zhi-Hong Du、Bao-Xiu Tao、Meng Yuan、Wen-Juan Qin、Yan-Li Xu、Pei Wang、Chao-Shan Da

  DOI：10.1021/acs.orglett.0c01407

  日期：2020.6.5

  beta-Turn tetrapeptides were demonstrated to catalyze asymmetric aldol reaction of alpha-branched aldehydes and acarbonyl aldehydes, i.e. glyoxylates and alpha-ketoaldehydes, to biomimetically synthesize acyclic all-carbon quaternary center-bearing 1,4-dicarbonyls in high yield and excellent enantioselectivity under mild conditions. The spatially restricted environment of the tetrapeptide warrants high enantioselectivity and yield with broad substrates. Using this protocol, (R)-pantolactone, the key intermediate of vitamin BS, was readily accessed in a practical, efficient, and environmentally benign process from inexpensive starting materials.
• Barlin, Gordon B.; Davies, Les P.; Harrison, Peter W., Australian Journal of Chemistry, 1994, vol. 47, # 11, p. 1989 - 2000
  作者：Barlin, Gordon B.、Davies, Les P.、Harrison, Peter W.、Jacobsen, Noel W.、Willis, Anthony C.

  DOI：——

  日期：——
• Maytansinoids. Synthesis of a fragment of known absolute configuration involving chiral centers C-6 and C-7
  作者：William J. Elliott、Josef Fried

  DOI：10.1021/jo00876a027

  日期：1976.7