1,4-Dioxo-1,4-dihydro-naphthalene-2-carboxylic acid (R)-4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester | 208335-48-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,4-Dioxo-1,4-dihydro-naphthalene-2-carboxylic acid (R)-4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester
• 英文别名: [(3R)-4,4-dimethyl-2-oxooxolan-3-yl] 1,4-dioxonaphthalene-2-carboxylate
• CAS: 208335-48-2
• 化学式: C₁₇H₁₄O₆
• 分子量: 314.295
• InChiKey: YSUYRPYPFRZUKC-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  86.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,4-Dioxo-1,4-dihydro-naphthalene-2-carboxylic acid (R)-4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 (3''R)-4'',4''-dimethyl-2''-oxotetrahydrofuran-3''-yl 5-hydroxy-2-(2'-oxoethyl)-2,3-dihydronaphtho[1,2-b]furan-4-carboxylate
  参考文献：
  名称：

  摘要：

  The Diels Alder addition of naphthoquinone (2a) to 1-trimethylsilyloxybuta-1,3-diene (3) afforded a 1.4 : 1 ratio of Diels Alder adducts (5a) and (6a) which were easily separated by flash chromatography. Individual treatment of adducts (5a) and (6a) with tin( IV) chloride afforded dihydrofuran (11a) as an inseparable 1 : 1 mixture of diastereomers. Diels Alder addition of naphthoquinones (2a) and (2b) to 1-methoxy-1-trimethylsilyloxybuta-1,3-diene (4) followed by treatment with tin( IV) chloride afforded dihydrofurans (12a) and (12b) respectively, both as inseparable 1 : 1 mixtures of C2 epimers. Removal of the pantolactone auxiliary from dihydrofuran (12a) was achieved by using lithium borohydride, affording aldehyde (13) which underwent oxidative rearrangement by using ceric ammonium nitrate to pyranonaphthoquinone (14). The inability to separate the individual C2 epimers of dihydrofuran (12a) easily by flash chromatography did not allow extension of this method to an enantioselective synthesis of pyranonaphthoquinone (14). Pyranonaphthoquinone (14) is closely related to the 3C protease inhibitor thysanone (15).

  DOI：

  10.1071/ch00074
• 作为产物：
  描述：

  1,4-二甲氧基-2-萘甲酸甲酯 在 4-二甲氨基吡啶 、 sodium hydroxide 、 ammonium cerium(IV) nitrate 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 3.16h， 生成 1,4-Dioxo-1,4-dihydro-naphthalene-2-carboxylic acid (R)-4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  不对称狄尔斯-手性萘醌中环戊二烯的Al代加成

  摘要：

  在路易斯酸条件下，在C-2处带有手性助剂的1,4-萘醌的Diels-Alder反应与环戊二烯反应，得到相应的Diels-Alder加合物。使用（R）-泛酸内酯，（S）-N-甲基-2-羟基琥珀酰亚胺和反式-2-苯基环己醇作为助剂可得到高水平的非对映异构体过量。使用Oppolzer的樟脑和（R）-（+）-4-苄基-2-恶唑烷酮作为助剂可实现中等程度的不对称诱导。泛内酯加合物的X射线晶体学分析能够确定所获得的所有加合物的立体化学。

  DOI：

  10.1016/s0957-4166(98)00087-1

文献信息

• Asymmetric Michael addition of 2-trimethylsilyloxyfuran to chiral naphthoquinones
  作者：Margaret A Brimble、John F McEwan、Peter Turner

  DOI：10.1016/s0957-4166(98)00088-3

  日期：1998.4

  various Lewis acids afforded the corresponding furofuran adducts 5–12. Moderate levels of diastereomeric excess were obtained using (R)-pantolactone, (S)-N-methyl-2-hydroxysuccinimide and (R)-(+)-4-benzyl-2-oxazolidinone as chiral auxiliaries. Low asymmetric induction was achieved using a camphorsultam auxiliary. X-Ray crystallographic analysis of the pantolactone adduct enabled determination of the absolute

  使用各种路易斯酸，在C-2 1 – 4处带有手性助剂的1,4-萘醌的不对称迈克尔反应与2-三甲基甲硅烷基氧基呋喃反应，得到相应的呋喃呋喃加合物5 – 12。使用（R）-泛内酯，（S）-N-甲基-2-羟基琥珀酰亚胺和（R）-（+）-4-苄基-2-恶唑烷酮作为手性助剂获得中等水平的非对映异构体过量。使用樟脑辅助剂可实现低不对称诱导。泛内酯加合物的X射线晶体学分析能够确定所获得的所有加合物的绝对立体化学。证据表明，TMS-呋喃的添加是通过 提供了迈克尔反应而不是狄尔斯-阿尔德环加成反应。
• Asymmetric Diels–Alder addition of cyclopentadiene to chiral naphthoquinones
  作者：Margaret A Brimble、John F McEwan、Peter Turner

  DOI：10.1016/s0957-4166(98)00087-1

  日期：1998.4

  cyclopentadiene under Lewis acid conditions afforded the corresponding Diels–Alder adducts. High levels of diastereomeric excess were obtained using (R)-pantolactone, (S)-N-methyl-2-hydroxysuccinimide and trans-2-phenylcyclohexanol as auxiliaries. Moderate asymmetric induction was achieved using Oppolzer's camphorsultam and (R)-(+)-4-benzyl-2-oxazolidinone as auxiliaries. X-Ray crystallographic analysis of the

  在路易斯酸条件下，在C-2处带有手性助剂的1,4-萘醌的Diels-Alder反应与环戊二烯反应，得到相应的Diels-Alder加合物。使用（R）-泛酸内酯，（S）-N-甲基-2-羟基琥珀酰亚胺和反式-2-苯基环己醇作为助剂可得到高水平的非对映异构体过量。使用Oppolzer的樟脑和（R）-（+）-4-苄基-2-恶唑烷酮作为助剂可实现中等程度的不对称诱导。泛内酯加合物的X射线晶体学分析能够确定所获得的所有加合物的立体化学。
• ——
  作者：Margaret A. Brimble、Richard J. Elliott、John F. McEwan

  DOI：10.1071/ch00074

  日期：——

  The Diels Alder addition of naphthoquinone (2a) to 1-trimethylsilyloxybuta-1,3-diene (3) afforded a 1.4 : 1 ratio of Diels Alder adducts (5a) and (6a) which were easily separated by flash chromatography. Individual treatment of adducts (5a) and (6a) with tin( IV) chloride afforded dihydrofuran (11a) as an inseparable 1 : 1 mixture of diastereomers. Diels Alder addition of naphthoquinones (2a) and (2b) to 1-methoxy-1-trimethylsilyloxybuta-1,3-diene (4) followed by treatment with tin( IV) chloride afforded dihydrofurans (12a) and (12b) respectively, both as inseparable 1 : 1 mixtures of C2 epimers. Removal of the pantolactone auxiliary from dihydrofuran (12a) was achieved by using lithium borohydride, affording aldehyde (13) which underwent oxidative rearrangement by using ceric ammonium nitrate to pyranonaphthoquinone (14). The inability to separate the individual C2 epimers of dihydrofuran (12a) easily by flash chromatography did not allow extension of this method to an enantioselective synthesis of pyranonaphthoquinone (14). Pyranonaphthoquinone (14) is closely related to the 3C protease inhibitor thysanone (15).