(3R,4R,5R)-3-(1,3-Benzodioxol-5-ylmethyl)-4-<(1,3-benzodioxol-5-yl)bis(phenylthio)methyl>-5-(l-menthyloxy)dihydro-2(3H)-furanone | 158665-02-2

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 呋喃类木脂素
• 英文名称: (3R,4R,5R)-3-(1,3-Benzodioxol-5-ylmethyl)-4-<(1,3-benzodioxol-5-yl)bis(phenylthio)methyl>-5-(l-menthyloxy)dihydro-2(3H)-furanone
• 英文别名: (3R,4R,5R)-4-[1,3-benzodioxol-5-yl-bis(phenylsulfanyl)methyl]-3-(1,3-benzodioxol-5-ylmethyl)-5-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxyoxolan-2-one
• CAS: 158665-02-2
• 化学式: C₄₂H₄₄O₇S₂
• 分子量: 724.939
• InChiKey: YUQQCVFCMALLLW-XAJKZUPQSA-N

物化性质

• 沸点：
  818.313±65.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.326±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.1
• 重原子数：
  51
• 可旋转键数：
  11
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (3R,4R,5R)-3-(1,3-Benzodioxol-5-ylmethyl)-4-<(1,3-benzodioxol-5-yl)bis(phenylthio)methyl>-5-(l-menthyloxy)dihydro-2(3H)-furanone 在 氢氧化钾 、 sodium tetrahydroborate 、 nickel dichloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以56%的产率得到荜澄茄内酯
  参考文献：
  名称：

  Enantioselective Synthesis of Natural Dibenzylbutyrolactone Lignans (-)-Enterolactone, (-)-Hinokinin, (-)-Pluviatolide, (-)-Enterodiol, and Furofuran Lignan (-)-Eudesmin via Tandem Conjugate Addition to .gamma.-Alkoxybutenolides

  摘要：

  A general and efficient method is described for the asymmetric synthesis of a variety of lignans. 5-(Menthyloxy)-2(5H)-furanones 5 proved to be excellent chiral synthons in this respect and could be transformed with complete stereoselectivity into a number of lignans. The addition of lithiated dithianes 7 to enantiomerically pure butenolides 5 was followed by quenching of the resulting lactone enolate anions with a benzylbromide (9) or with an aldehyde (6). This tandem addition quenching procedure gave the diastereomerically pure adducts 11, 26, or 27 in 50-67% yield, with a carbon skeleton as found in most natural lignans. As examples of the wide applicability of this method, the syntheses of the enantiomerically pure natural lignans (-)-hinokinin (23b), (-)-enterolactone (24a), (-)-pluviatolide (24c), and (-)-enterodiol (25) in overall yields of 29-37% from 5a and (-)-eudesmin (30) in 16% overall yield from 5b are described.

  DOI：

  10.1021/jo00099a033
• 作为产物：
  描述：

  胡椒醇 在 正丁基锂 、 四甲基乙二胺 、 三溴化磷 作用下， 以 乙醚 为溶剂， 反应 22.5h， 生成 (3R,4R,5R)-3-(1,3-Benzodioxol-5-ylmethyl)-4-<(1,3-benzodioxol-5-yl)bis(phenylthio)methyl>-5-(l-menthyloxy)dihydro-2(3H)-furanone
  参考文献：
  名称：

  Enantioselective Synthesis of Natural Dibenzylbutyrolactone Lignans (-)-Enterolactone, (-)-Hinokinin, (-)-Pluviatolide, (-)-Enterodiol, and Furofuran Lignan (-)-Eudesmin via Tandem Conjugate Addition to .gamma.-Alkoxybutenolides

  摘要：

  A general and efficient method is described for the asymmetric synthesis of a variety of lignans. 5-(Menthyloxy)-2(5H)-furanones 5 proved to be excellent chiral synthons in this respect and could be transformed with complete stereoselectivity into a number of lignans. The addition of lithiated dithianes 7 to enantiomerically pure butenolides 5 was followed by quenching of the resulting lactone enolate anions with a benzylbromide (9) or with an aldehyde (6). This tandem addition quenching procedure gave the diastereomerically pure adducts 11, 26, or 27 in 50-67% yield, with a carbon skeleton as found in most natural lignans. As examples of the wide applicability of this method, the syntheses of the enantiomerically pure natural lignans (-)-hinokinin (23b), (-)-enterolactone (24a), (-)-pluviatolide (24c), and (-)-enterodiol (25) in overall yields of 29-37% from 5a and (-)-eudesmin (30) in 16% overall yield from 5b are described.

  DOI：

  10.1021/jo00099a033

文献信息

• Synthesis and Cytotoxicity of Novel Lignans
  作者：Oskar Middel、Herman J. Woerdenbag、Wim van Uden、Arjan van Oeveren、Johan F. G. A. Jansen、Ben L. Feringa、Antonius W. T. Konings、Niesko Pras、Richard M. Kellogg

  DOI：10.1021/jm00012a010

  日期：1995.6

  In this study the syntheses of 11 novel lignans are described. Their cytotoxicities are studied in GLC(4), a human small cell lung carcinoma cell line, using the microculture tetrazolium (MTT) assay. Ten of these compounds were substituted with a menthyloxy group on the 5-position of the lactone. These compounds can easily be prepared in (novel) 'one-pot', three- or four-step syntheses. In addition, methods for controlling the stereogenic centers are described. Furthermore, five naturally occurring podophyllotoxin-related compounds were tested. The cytotoxicities of all lignan compounds, and of three non-lignan intermediates originating from the syntheses, were compared with the clinically applied anticancer agents etoposide, teniposide, and cisplatin. Most compounds showed moderate to high activities against GLC(4), and two of the compounds containing a menthyloxy group showed activities comparable to the reference cytotoxic agents.
• Enantioselective Synthesis of Natural Dibenzylbutyrolactone Lignans (-)-Enterolactone, (-)-Hinokinin, (-)-Pluviatolide, (-)-Enterodiol, and Furofuran Lignan (-)-Eudesmin via Tandem Conjugate Addition to .gamma.-Alkoxybutenolides
  作者：Arjan van Oeveren、Johan F. G. A. Jansen、Ben L. Feringa

  DOI：10.1021/jo00099a033

  日期：1994.10

  A general and efficient method is described for the asymmetric synthesis of a variety of lignans. 5-(Menthyloxy)-2(5H)-furanones 5 proved to be excellent chiral synthons in this respect and could be transformed with complete stereoselectivity into a number of lignans. The addition of lithiated dithianes 7 to enantiomerically pure butenolides 5 was followed by quenching of the resulting lactone enolate anions with a benzylbromide (9) or with an aldehyde (6). This tandem addition quenching procedure gave the diastereomerically pure adducts 11, 26, or 27 in 50-67% yield, with a carbon skeleton as found in most natural lignans. As examples of the wide applicability of this method, the syntheses of the enantiomerically pure natural lignans (-)-hinokinin (23b), (-)-enterolactone (24a), (-)-pluviatolide (24c), and (-)-enterodiol (25) in overall yields of 29-37% from 5a and (-)-eudesmin (30) in 16% overall yield from 5b are described.