(R)-tert-butyl 2-(benzyloxymethyl)-5-iodo-4-oxo-6-propyl-3,4-dihydropyridine-1(2H)-carboxylate | 1448666-68-9

• 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: (R)-tert-butyl 2-(benzyloxymethyl)-5-iodo-4-oxo-6-propyl-3,4-dihydropyridine-1(2H)-carboxylate
• 英文别名: tert-butyl (2R)-5-iodo-4-oxo-2-(phenylmethoxymethyl)-6-propyl-2,3-dihydropyridine-1-carboxylate
• CAS: 1448666-68-9
• 化学式: C₂₁H₂₈INO₄
• 分子量: 485.362
• InChiKey: SUGVJLXYWXNFRK-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-tert-butyl 2-(benzyloxymethyl)-5-iodo-4-oxo-6-propyl-3,4-dihydropyridine-1(2H)-carboxylate 、 丙烯酸乙酯 在 四(三苯基膦)钯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以67%的产率得到(R,E)-ethyl 3-(6-(benzyloxymethyl)-4-oxo-2-propyl-1,4,5,6-tetrahydropyridin-3-yl)acrylate
  参考文献：
  名称：

  Gold-Mediated Synthesis and Functionalization of Chiral Halopyridones

  摘要：

  A rapid and efficient one-step halopyridone synthesis has been developed based on gold-catalyzed cyclization of beta-amino-ynone intermediates and halodeauration process.

  DOI：

  10.1021/jo400827b
• 作为产物：
  描述：

  在 N-碘代丁二酰亚胺 、 silver hexafluoroantimonate 、 三苯基膦氯金 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.08h， 以47%的产率得到(R)-tert-butyl 2-(benzyloxymethyl)-5-iodo-4-oxo-6-propyl-3,4-dihydropyridine-1(2H)-carboxylate
  参考文献：
  名称：

  Gold-Mediated Synthesis and Functionalization of Chiral Halopyridones

  摘要：

  A rapid and efficient one-step halopyridone synthesis has been developed based on gold-catalyzed cyclization of beta-amino-ynone intermediates and halodeauration process.

  DOI：

  10.1021/jo400827b

文献信息

• PHOTOPROTECTIVE COMPOUNDS, COMPOSITIONS INCLUDING SAME AND USES THEREOF
  申请人：UNIVERSITE DE RENNES 1

  公开号：US20160067162A1

  公开（公告）日：2016-03-10

  A compound of formula (I): wherein: R1 is H, benzyl, —CH 2 —O-benzyl, a straight or branched C1-C12 alkyl radical, a hydroxyalkyl radical or a polyhydroxyalkyl radical, R2 is H; a straight or branched C1-C12 alkyl radical; a —(CH 2 ) 3 —CH═CH 2 radical; a phenyl, naphthyl, furan, thiophene or pyrazole radical, optionally substituted by at least one group selected among methoxy, phenoxy, halogen, dimethylamine, trifluoromethyl and alkynyl, R3 is H; a vinyl radical optionally substituted by a carboxyalkyl; a nitrile; a carboxamide; a phenyl, naphthyl, furan, thiophene or pyrazole radical, optionally substituted by at least one group selected among methoxy, phenoxy, halogen, dimethylamine, trifluoromethyl and alkynyl; an aminoalkyl or aminocarboxyl radical; or an alkoxy radical, R4 is H, a protective grouping, a straight or branched C1-C12 alkyl radical, a hydroxyalkyl radical or a polyhydroxyalkyl radical, and when: R2 is H, R3 is —NHCOOC(CH 3 ) 3 , R2 is a propyl, R3 is —CH═CH—COO—C 2 H 5 or R1=R3=R4=H, R2 is a non-substituted phenyl, R3 is —CH═CH—COO—C 2 H 5 or —NHCOOC(CH 3 ) 3 , R2 is a phenyl substituted in the para position, R3 is H.

  化合物的化学式(I)：其中：R1为H，苄基，-CH2-O-苄基，直链或支链C1-C12烷基基团，羟基烷基基团或多羟基烷基基团，R2为H；直链或支链C1-C12烷基基团；-（ ）3-CH═ 基团；苯基，萘基，呋喃基，噻吩基或吡唑基团，可选地被至少一个在甲氧基，苯氧基，卤素，二甲胺，三氟甲基和炔基中选择的基团取代，R3为H；可选地被羧基烷基取代的乙烯基基团；腈基；羧酰胺基团；苯基，萘基，呋喃基，噻吩基或吡唑基团，可选地被至少一个在甲氧基，苯氧基，卤素，二甲胺，三氟甲基和炔基中选择的基团取代；氨基烷基或氨基羧基基团；或烷氧基基团，R4为H，保护基，直链或支链C1-C12烷基基团，羟基烷基基团或多羟基烷基基团，当R2为H时，R3为-NHCOOC(CH3)3，当R2为丙基时，R3为-CH═CH-COO-C2H5或R1=R3=R4=H，当R2为未取代的苯基时，R3为-CH═CH-COO- 或-NHCOOC( )3，当R2为在对位上取代的苯基时，R3为H。