(4S)-4-benzyl-3-{(R)-2-[(S)-(4-benzyloxy-3-methoxyphenyl)(hydroxy)methyl]-4-pentenoyl}-2-oxazolidinone | 865872-68-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (4S)-4-benzyl-3-{(R)-2-[(S)-(4-benzyloxy-3-methoxyphenyl)(hydroxy)methyl]-4-pentenoyl}-2-oxazolidinone
• 英文别名: (4S)-4-benzyl-3-{(R)-2-[(S)-(4-benzyloxy-3-methoxyphenyl)hydroxymethyl]-4-pentenoyl}-2-oxazolidinone；(4S)-4-benzyl-3-[(2R)-2-[(S)-hydroxy-(3-methoxy-4-phenylmethoxyphenyl)methyl]pent-4-enoyl]-1,3-oxazolidin-2-one
• CAS: 865872-68-0
• 化学式: C₃₀H₃₁NO₆
• 分子量: 501.579
• InChiKey: WYNVANKGGKAFHI-BXTSTYNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  85.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4S)-4-benzyl-3-{(R)-2-[(S)-(4-benzyloxy-3-methoxyphenyl)(hydroxy)methyl]-4-pentenoyl}-2-oxazolidinone 在 吡啶 、 2,6-二甲基吡啶 、 甲醇 、 sodium periodate 、 四氧化锇 、 锂硼氢 、 四丁基氟化铵 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 37.5h， 生成
  参考文献：
  名称：

  橄榄石型木脂素的合成及其抗氧化活性。

  摘要：

  首次合成了天然橄榄石的对映异构体类型橄榄石型木脂素，以评估橄榄石结构与其抗氧化活性之间的关系。与其他合成的四氢呋喃木脂素的抗氧化剂活性的比较表明，叔羟基具有降低的活性。还观察到橄榄石的两个酚基对抗氧化活性的不同作用。

  DOI：

  10.1271/bbb.69.113
• 作为产物：
  描述：

  4-苄氧基-3-甲氧基苯甲醛 、 (S)-4-苄基-3-(戊-4-烯酰基)恶唑烷-2-酮 在 三甲基氯硅烷 、 三乙胺 、 magnesium chloride 作用下， 以 乙酸乙酯 为溶剂， 反应 16.0h， 以99%的产率得到(4S)-4-benzyl-3-{(R)-2-[(S)-(4-benzyloxy-3-methoxyphenyl)(hydroxy)methyl]-4-pentenoyl}-2-oxazolidinone
  参考文献：
  名称：

  橄榄石型木脂素的合成及其抗氧化活性。

  摘要：

  首次合成了天然橄榄石的对映异构体类型橄榄石型木脂素，以评估橄榄石结构与其抗氧化活性之间的关系。与其他合成的四氢呋喃木脂素的抗氧化剂活性的比较表明，叔羟基具有降低的活性。还观察到橄榄石的两个酚基对抗氧化活性的不同作用。

  DOI：

  10.1271/bbb.69.113

文献信息

• First Stereoselective Synthesis of<i>meso</i>-Secoisolariciresinol and Comparison of Its Biological Activity with (+) and (−)-Secoisolariciresinol
  作者：Takuya SUGAHARA、Satoshi YAMAUCHI、Ai KONDO、Fumi OHNO、Siori TOMINAGA、Yuki NAKASHIMA、Taro KISHIDA、Koichi AKIYAMA、Masafumi MARUYAMA

  DOI：10.1271/bbb.70358

  日期：2007.12.23

  The first stereoselective synthesis of meso-secoisolariciresinol is reported. A comparison of the cytotoxic and immunosuppressive activity between meso-secoisolariciresinol and optically active secoisolariciresinols was similarly performed for the first time. Both enantiomers of secoisolariciresinol accelerated IgM production, although meso-secoisolariciresinol did not affect IgM production. Only meso-secoisolariciresinol showed cytotoxic activity.

  首次报道了内消旋异落叶松树脂醇的立体选择性合成。类似地，首次对内消旋异落叶松树脂醇和旋光异落叶松树脂醇之间的细胞毒性和免疫抑制活性进行了比较。开环异落叶松树脂醇的两种对映体均可加速 IgM 的产生，但内消旋开环异落叶松树脂醇不影响 IgM 的产生。仅内消旋异落叶松树脂醇表现出细胞毒活性。
• Antimicrobial Activity of Stereoisomers of Butane-Type Lignans
  作者：Yuya KAWAGUCHI、Satoshi YAMAUCHI、Kenta MASUDA、Hisashi NISHIWAKI、Koichi AKIYAMA、Masafumi MARUYAMA、Takuya SUGAHARA、Taro KISHIDA、Yojiro KOBA

  DOI：10.1271/bbb.90167

  日期：2009.8.23

  The relationship between the stereochemistry and antimicrobial activity of butane-type lignans was clarified. All stereoisomers of dihydroguaiaretic acid (DGA) showed both antibacterial and antifungal activity. The (+)- and (−)-7,7′-dioxodihydroguaiaretic acid (ODGA) also showed both antibacterial and antifungal activity, while meso-ODGA did not show antibacterial activity, but showed antifungal activity. No activity of any stereoisomer of secoisolariciresinol (SECO) was apparent.

  阐明了丁烷类木脂素的立体化学与抗菌活性之间的关系。二氢愈创木脂酸（DGA）的所有立体异构体都具有抗菌和抗真菌活性。(+)-和(-)-7,7′-二氧代二氢愈创木脂酸（ODGA）也显示出抗菌和抗真菌活性，而中-ODGA 没有显示出抗菌活性，但显示出抗真菌活性。SEcoisolariciresinol（SECO）的任何立体异构体都没有明显的活性。
• Effect of Benzylic Oxygen on the Antioxidant Activity of Phenolic Lignans
  作者：Satoshi Yamauchi、Yoshimasa Hayashi、Yuki Nakashima、Takuya Kirikihira、Kazuki Yamada、Toshiya Masuda

  DOI：10.1021/np050089s

  日期：2005.10.1

  It has been clarified in the present investigation that a high degree of oxidation at the benzylic position of phenolic lignans bearing a 4-hydroxy-3-methoxybenzyl group reduces their antioxidant activity and that the antioxidant activity of the bis(4-hydroxy-3-methoxybenzyl)tetrahydrofuran lignan 2 is higher than that of the corresponding gamma-butyrolactone lignan 1. This was demonstrated by comparing the antioxidant activities of compounds 1 and 2 with those of the (benzyl)(hydroxybenzyl)tetrahydrofurans 3 and 4, the bis(hydroxybenzyl)tetrahydrofurans 7 and 8, the (benzoyl)(benzyl)tetrahydrofuran 6, and the dibenzoyltetrahydrofuran 9. The activity level of compound 2 was approximately the same potency as that of the tetrahydronaphthalene-tetrahydrofuran 5. These compounds possess either a 4-hydroxy3-methoxybenzyl group or a 4-hydroxy-3-methoxybenzoyl group as the benzyl or benzoyl group. An examination of radical scavenging activity showed differences of activity between diastereomers. To make this comparison possible, compounds 1-9 were synthesized using new synthetic routes for several of these lignans. In this investigation, stereoisomers of the (benzyl)(hydroxybenzyl)tetrahydrofurans 3 and 4 and liovils 7 and 8 were synthesized for the first time.