2-(β-D-glucopyranosyloxy)-3,4-dihydro-4-hydroxy-7-methoxy-2H-1,4-benzoxazin-3-one | 18607-79-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(β-D-glucopyranosyloxy)-3,4-dihydro-4-hydroxy-7-methoxy-2H-1,4-benzoxazin-3-one
• 英文别名: (2R)-2-O-β-D-glucopyranosyl-4-hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one；2-(2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one)β-D-glucopyranoside；2-O-β-glucopyranosyl-4-hydroxy-7-methoxy-1,4(2H)-benzoxazin-3-one；2-β-D-glucopyranosyloxy-4-hydroxy-7-methoxy-1,4-benzoxazin-3-one；2-O-β-D-Glucopyranosyl-4-hydroxy-7-methoxy-1,4-benzoxazin-3-one；2,4-dihydroxy-7-methoxy-1,4-benzoxazine-3-one glucoside；4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl beta-D-glucopyranoside；4-hydroxy-7-methoxy-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4-benzoxazin-3-one
• CAS: 18607-79-9
• 化学式: C₁₅H₁₉NO₁₀
• 分子量: 373.317
• InChiKey: WTGXAWKVZMQEDA-XGHDNVSXSA-N

物化性质

• 沸点：
  680.9±65.0 °C(Predicted)
• 密度：
  1.71±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  158
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-(β-D-glucopyranosyloxy)-3,4-dihydro-4-hydroxy-7-methoxy-2H-1,4-benzoxazin-3-one 在 盐酸 、 锌 作用下， 反应 12.0h， 以50 mg的产率得到2-O-葡糖基-7-甲氧基-1,4(2H)-苯并恶嗪-3-酮
  参考文献：
  名称：

  来自薏苡仁变种的苯并恶嗪酮。马园

  摘要：

  摘要 2-O-β-D-吡喃葡萄糖基-7-甲氧基-1,4(2H)-benzoxazin-3-one 和三个同源物的绝对构型从薏苡仁中分离出来。马源经X射线分析和化学相关确定为2R型。所有同系物和薏苡醇的 13 C NMR 谱均已完全归属。

  DOI：

  10.1016/0031-9422(85)80035-2
• 作为产物：
  描述：

  尿苷(5')二氢二磷酰(1)-alpha-D-葡萄糖 、 丁布 在 Mythimna separata midgut tissue 作用下， 以 CHES buffer 、 水 、 二甲基亚砜 为溶剂， 反应 1.5h， 生成 2-(β-D-glucopyranosyloxy)-3,4-dihydro-4-hydroxy-7-methoxy-2H-1,4-benzoxazin-3-one
  参考文献：
  名称：

  Species-Specific Glucosylation of DIMBOA in Larvae of the Rice Armyworm

  摘要：

  DIMBOA[2,4-二羟基-7-甲氧基-2H-1,4-苯并恶嗪-3(4H)-酮]是一种苯并恶嗪类化合物（Bx），是玉米、小麦和黑麦等禾本科植物化学防御系统的一部分。当用含有 DIMBOA 的人工饲料喂养蚕蛾幼虫时，它们会在三天内死亡。与此相反，水稻、玉米、高粱、小麦等作物的严重害虫 Mythimna separata 幼虫在同样的饲料中生长良好。三种葡糖苷[1-（2-羟基-4-甲氧基苯基氨基）-1-脱氧-β-吡喃葡萄糖苷-1,2-氨基甲酸酯（甲氧基葡糖苷氨基甲酸酯）、2-O-β-吡喃葡萄糖基-4-羟基-7-甲氧基-2H-1、通过 LC-MS 和 NMR 分析，从喂食了 M. separata 的粪便中鉴定出了 2-O-β-吡喃葡萄糖基-4-羟基-7-甲氧基-2H-1,4-苯并恶嗪-3(4H)-酮（DIMBOA-2-O-Glc）和 2-O-β-吡喃葡萄糖基-7-甲氧基-2H-1,4-苯并恶嗪-3(4H)-酮（HMBOA-2-O-Glc）。通过 LC-MS 和 NMR 分析，确定了以含 DIMBOA 的食物喂养的 M. separata 的粪便中含有 DIMBOA。此外，在有 UDP-d-葡萄糖存在的情况下，DIMBOA 与 M. separata 的中肠组织悬浮液孵育会产生 DIMBOA-2-O-Glc。这些发现有力地表明，UDP-葡萄糖基转移酶的葡萄糖基化作用对于解毒以规避寄主植物对分离贻贝幼虫的防御非常重要。

  DOI：

  10.1271/bbb.80903

文献信息

• Chemical studies on 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one in connection with 6-methoxy-2-benzoxazolinone, an auxin-inhibiting substance of Zea mays L.
  作者：Seiji Kosemura、Shosuke Yamamura、Toyoaki Anai、Koji Hasegawa

  DOI：10.1016/0040-4039(94)88287-8

  日期：1994.10

  Some chemical studies on 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (DIMBOA, 1) and related compounds from Zea mays L. have been carried out, where DIMBOA (1) has been very rapidly converted into 6-methoxy-2-benzoxazolinone (MBOA, 2), an auxin-inhibiting substanse of maize, in the presence of acetic anhydride at room temperature. Therefore, such an enzymatic acylation of N-OH group of DIMBOA

  已经对来自玉米的2,4-二羟基-7-甲氧基-2 H -1,4-苯并恶嗪-3（4 H）-one（DIMBOA，1）和相关化合物进行了一些化学研究，其中DIMBOA （1）在室温下存在乙酸酐的情况下，已非常迅速地转化为6-甲氧基-2-苯并恶唑啉酮（MBOA，2），即一种玉米生长素抑制物质。因此，推测如体外的DIMBOA（1）的N-OH基团的酶促酰化作用对光致变色起重要作用。
• Non-induced cyclic hydroxamic acids in wheat during juvenile stage of growth
  作者：Eri Nakagawa、Takashi Amano、Nobuhiro Hirai、Hajime Iwamura

  DOI：10.1016/0031-9422(94)00831-d

  日期：1995.4

  2,4-Dihydroxy-1,4-benzoxazine-3-one glucoside (DIBOA-G) and its methoxy analogue, 2,4-dihydroxy-7-methoxy-1,4-benzoxazine-3-one glucoside (DIMBOA-G), were present in germinating wheat (Triticum aestivum); the corresponding aglycones, DIBOA and DIMBOA, appeared soon after germination. The amounts of these compounds reached a maximum 12-48 hours after germination, and then decreased to undetectable levels as the plants began autotrophic growth. The time of their appearance was little affected by using seeds either sterilized or non-sterilized, by infection with pathogens and wounding with a razor blade. The concentration of DIBOA was found to be 0.2-0.3 nmol mg(-1) fr. wt (0.2-0.3 mM if the density of plant tissue is assumed to be uniform and unity) and that of DIMBOA was 0.7-1.0 nmol mg(-1) (0.7-1.0 mM). The aglycones retarded the germ tube growth of species of fungi at 0.3 mM. These observations suggest that the appearance of benzoxazinones is as defence compounds in the juvenile stage of growth. [C-14]Anthranilic acid was incorporated into DIBOA-G and DIMBOA-G when administered to embryos isolated from pre-emerging seeds, showing that the series of compounds are generated by de novo synthesis.