3β-hydroxy-5α,6α-epoxy-7-megastigmen-9-one | 175418-93-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 3β-hydroxy-5α,6α-epoxy-7-megastigmen-9-one
• 英文别名: 3α-hydroxy-5,6-epoxy-7-megastigmen-9-one；(3E)-4-[(1S,4R,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept-1-yl]but-3-en-2-one；(E)-4-[(1S,4R,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]but-3-en-2-one
• CAS: 175418-93-6
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: VYKLRWGPNUVKNC-BJEXPOHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β-hydroxy-5α,6α-epoxy-7-megastigmen-9-one 在 硫酸 作用下， 生成 (E)-4-(r-1',t-2',c-4'-trihydroxy-2',6',6'-trimethylcyclohexyl)but-3-em-2-one
  参考文献：
  名称：

  - （±）ë - （1,2,4-三羟基-2,6,6- tirmethylcyclohexyl） -丁-3-烯-2-酮：一种新型的类胡萝卜素降解从新西兰百里香分离（百里香）蜜

  摘要：

  从β-紫罗兰酮开始描述了标题化合物的外消旋合成。关键步骤包括三烯的选择性氢硼化，然后由钼介导的所得均烯丙基醇的环氧化，随后环氧化物的开环，得到标题化合物。

  DOI：

  10.1016/s0040-4039(00)79850-9
• 作为产物：
  描述：

  euodionoside A 在 hesperidinase 、 emulsin 、 水 作用下， 反应 15.0h， 以82%的产率得到3β-hydroxy-5α,6α-epoxy-7-megastigmen-9-one
  参考文献：
  名称：

  Euodionosides A–G: Megastigmane glucosides from leaves of Euodia meliaefolia

  摘要：

  From a 1-BuOH-soluble fraction of the MeOH extract of leaves of Euodia metiaefolia, collected in Okinawa, seven megastigmane glucosides, named euodionosides A-G, were isolated together with three known megastgmane glucosides, and two aliphatic and three phenolic compounds. Their structures were elucidated through a combination of spectroscopic analyses and application of the modified Mosher's method. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2008.01.020

文献信息

• PARRY, ANDREW D.;NEILL, STEVEN J.;HORGAN, ROGER, PHYTOCHEMISTRY, 29,(1990) N, C. 1033-1039
  作者：PARRY, ANDREW D.、NEILL, STEVEN J.、HORGAN, ROGER

  DOI：——

  日期：——
• Synthesis of (±)-E-(1,2,4-trihydroxy-2,6,6-tirmethylcyclohexyl)-but-3-en-2-one: A novel degraded carotenoid isolated from New Zealand thyme (thymus vulgaris) honey
  作者：Susan J. Broom、Richard M. Ede、Alistair L. Wilkins

  DOI：10.1016/s0040-4039(00)79850-9

  日期：1992.5

  A racemic synthesis of the title compound is described starting from β-ionone. The key steps involve selective hydroboration of a triene, followed by molybdenum mediated epoxidation of the resulting homoallylic alcohol with subsequent ring opening of the epoxide to give the title compound.

  从β-紫罗兰酮开始描述了标题化合物的外消旋合成。关键步骤包括三烯的选择性氢硼化，然后由钼介导的所得均烯丙基醇的环氧化，随后环氧化物的开环，得到标题化合物。
• Euodionosides A–G: Megastigmane glucosides from leaves of Euodia meliaefolia
  作者：Miwako Yamamoto、Takeyuki Akita、Yuka Koyama、Etsuko Sueyoshi、Katsuyoshi Matsunami、Hideaki Otsuka、Takakazu Shinzato、Atsushi Takashima、Mitsunori Aramoto、Yoshio Takeda

  DOI：10.1016/j.phytochem.2008.01.020

  日期：2008.5

  From a 1-BuOH-soluble fraction of the MeOH extract of leaves of Euodia metiaefolia, collected in Okinawa, seven megastigmane glucosides, named euodionosides A-G, were isolated together with three known megastgmane glucosides, and two aliphatic and three phenolic compounds. Their structures were elucidated through a combination of spectroscopic analyses and application of the modified Mosher's method. (C) 2008 Elsevier Ltd. All rights reserved.

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