3-hydroxy-7,8-didehydro-β-ionone | 224631-90-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-hydroxy-7,8-didehydro-β-ionone
• 英文别名: 4-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-enyl]but-3-yn-2-one；4-[(4R)-4-hydroxy-2,6,6-trimethylcyclohexen-1-yl]but-3-yn-2-one
• CAS: 224631-90-7
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: SZKRSYBOEULCED-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-hydroxy-7,8-didehydro-β-ionone 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 48.0h， 生成 大马士酮
  参考文献：
  名称：

  C₁₃-Norisoprenoid Glucoconjugates from Lulo (Solanum quitoense L.) Leaves

  摘要：

  With the aid of multilayer coil countercurrent chromatography, subsequent acetylation, and liquid chromatographic purification of a glycosidic mixture obtained from lulo (Solanum quitoense L.) leaves, three C-13-norisoprenoid glucoconjugates were isolated in pure form. Their structures were elucidated by NMR, MS, and CD analyses to be the novel (GR,SR)-13-hydroxy-3-oxo-alpha-ionol 9-O-beta-D-glucopyranoside (4a), the uncommon (3S,5R,8R)-3,5-dihydroxy-6,7-megastigmadien-O-beta-D-glucopyranoside (citroside A) (5a), and the known (6S,9R)-vomifoliol 9-O-beta-D-glucopyranoside (6a). Enzymatic treatment of compound 5a showed the formation of 3-hydroxy-7,8-didehydro-beta-ionone (7), an; important lulo peeling volatile, which in its turn after chemical reduction and heated acid catalyzed rearrangement generates beta-damascenone (9) and 3-hydroxy-beta-damascone (10).

  DOI：

  10.1021/jf9807364
• 作为产物：
  描述：

  1,1-dimethylethyl{[(1R)-4-ethynyl-3,5,5-trimethylcyclohex-3-entl]oxy}dimethylsilane 在 manganese(IV) oxide 、 正丁基锂 、 氢氟酸 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 乙腈 为溶剂， 反应 16.17h， 生成 3-hydroxy-7,8-didehydro-β-ionone
  参考文献：
  名称：

  立体控制合成的糖苷大马士革酮前体

  摘要：

  利用不对称转移完成了旋光性β- D-吡喃葡萄糖苷7-10和11-14（糖苷大马士康酮前体）的立体控制合成。氢化 对α，β-炔属 酮类 手性钌配合物催化是关键步骤。

  DOI：

  10.1039/b208758h

文献信息

• Stereocontrolled Synthesis of Optically Active .BETA.-D-Glucopyranosides of 3-Hydroxy-7,8-didehydro-.BETA.-ionol.
  作者：Yumiko YAMANO、Yasuko WATANABE、Naoharu WATANABE、Masayoshi ITO

  DOI：10.1248/cpb.48.2017

  日期：——

  A stereocontrolled synthesis of optically active beta-D-glucopyranosides 1-4 of 3-hydroxy-7,8-didehydro-beta-ionol utilizing an asymmetric transfer hydrogenation to alpha,beta-acetylenic ketones catalyzed by chiral ruthenium complexes as the key step is described.

  立体控制合成3-羟基-7,8-二氢-β-紫罗兰醇的旋光性β-D-吡喃葡萄糖苷1-4，其中不对称转移氢化为手性钌配合物催化的α，β-炔基酮是关键步骤是描述。
• Stereocontrolled synthesis of glucosidic damascenone precursors
  作者：Yumiko Yamano、Yasuko Watanabe、Naoharu Watanabe、Masayoshi Ito

  DOI：10.1039/b208758h

  日期：2002.12.19

  A stereocontrolled synthesis of optically active β-D-glucopyranosides 7–10 and 11–14, glucosidic damascenone precursors, was accomplished utilizing an asymmetric transfer hydrogenation to α,β-acetylenic ketones catalyzed by chiral ruthenium complexes as the key step.

  利用不对称转移完成了旋光性β- D-吡喃葡萄糖苷7-10和11-14（糖苷大马士康酮前体）的立体控制合成。氢化 对α，β-炔属 酮类 手性钌配合物催化是关键步骤。
• C₁₃-Norisoprenoid Glucoconjugates from Lulo (<i>Solanum </i><i>q</i><i>uitoense</i> L.) Leaves
  作者：Coralia Osorio、Carmenza Duque、Yoshinori Fujimoto

  DOI：10.1021/jf9807364

  日期：1999.4.1

  With the aid of multilayer coil countercurrent chromatography, subsequent acetylation, and liquid chromatographic purification of a glycosidic mixture obtained from lulo (Solanum quitoense L.) leaves, three C-13-norisoprenoid glucoconjugates were isolated in pure form. Their structures were elucidated by NMR, MS, and CD analyses to be the novel (GR,SR)-13-hydroxy-3-oxo-alpha-ionol 9-O-beta-D-glucopyranoside (4a), the uncommon (3S,5R,8R)-3,5-dihydroxy-6,7-megastigmadien-O-beta-D-glucopyranoside (citroside A) (5a), and the known (6S,9R)-vomifoliol 9-O-beta-D-glucopyranoside (6a). Enzymatic treatment of compound 5a showed the formation of 3-hydroxy-7,8-didehydro-beta-ionone (7), an; important lulo peeling volatile, which in its turn after chemical reduction and heated acid catalyzed rearrangement generates beta-damascenone (9) and 3-hydroxy-beta-damascone (10).