(3RS,6RS)-3,6-dihydroxy-α-ionone | 39763-31-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (3RS,6RS)-3,6-dihydroxy-α-ionone
• 英文别名: trans-3,6-dihydroxy-α-ionone；(E)-4-(1beta,4alpha-Dihydroxy-2,6,6-trimethyl-2-cyclohexenyl)-3-butene-2-one；(E)-4-[(1R,4R)-1,4-dihydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]but-3-en-2-one
• CAS: 39763-31-0；39763-36-5；75281-40-2；75281-41-3；77610-78-7；80373-99-5；99881-89-7
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: NBUWBYRRHDLLJS-ILBNWAPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3RS,6RS)-3,6-dihydroxy-α-ionone 在 lithium aluminium tetrahydride 、 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 为溶剂， 生成 (+/-)-3,6-epoxy-5-hydroxy-5,6-dihydro-β-ionol
  参考文献：
  名称：

  SYNTHESIS AND STEREOCHEMISTRY OF 3,6-EPOXY-5-HYDROXY-5,6-DIHYDRO-β-IONOL, A NOVEL FLAVOR CONSTITUENT OF SUIFU TABACCO

  摘要：

  (±)-3,6-环氧-5-羟基-5,6-二氢-3-紫罗兰醇是由β-紫罗兰酮通过3,6-二羟基-α-紫罗兰酮合成的，其结构（包括相对构型）确定为（ ±)-2β,5β-环氧-2α-[3α-羟基-1(E)-丁烯基]-1β,3,3-三甲基环己烷-1α-醇，通过 X 射线分析。

  DOI：

  10.1246/cl.1980.757
• 作为产物：
  描述：

  (E)-4-(1',6'-Epoxy-2',2',6'-trimethyl-4'-cyclohexen-1'-yl)-3-buten-2-on 在 sodium metabisulfite 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以20.9 g的产率得到(3RS,6RS)-3,6-dihydroxy-α-ionone
  参考文献：
  名称：

  Chemoenzymatic resolution of cis- and trans-3,6-dihydroxy-α-ionone. Synthesis of the enantiomeric forms of dehydrovomifoliol and 8,9-dehydrotheaspirone

  摘要：

  A straightforward synthesis of both enantiomers of cis- and trans-3-acetoxy-6-hydroxy-alpha-ionone is described. The title compounds are prepared by resolution of the diastereoisomerically pure racemic 3,6-dihydroxy-alpha-ionone isomers. The latter process is based on two steps. The first is the enantio- and regioselective lipase-mediated acetylation of diols to afford the corresponding 3-acetoxy-derivatives. The second is the fractional crystallization of the latter compounds that increase their enantiomeric purity. These building blocks were used for the synthesis of both enantiomeric forms of the natural norterpenoids dehydrovomifoliol 3 and 8,9-dehydrotheaspirone 5. The latter compound is a natural flavor and its odor properties were evaluated by professional perfumers. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.10.014

文献信息

• Carotinoide mit 7-Oxabicyclo[2.2.1]heptyl-Endgruppen. Teil I. Versuch einer Synthese von Cycloviolaxanthin (= (3<i>S</i>,5<i>R</i>,6<i>R</i>,3′<i>S</i>,5′<i>R</i>,6′<i>R</i>)-3,6:3′,6′-Diepoxy-5,6,5′,6′-tetrahydro-β,β-carotin-5,5′-diol)
  作者：Michael Roman Gmünder、Conrad Hans Eugster

  DOI：10.1002/hlca.19900730719

  日期：1990.10.31

  Carotenoids with 7-Oxabicyclo[2,2.1]heptyl End Groups. Attempted Synthesis of Cycloviolaxanthin ( = (3S,5R,6S,3′S,5′R,6′R)-3,6:3′,6′- Diepoxy-5,6,5′,6′-tetrahydro-β,β-carotin-5,5′-diol)

  具有7-氧杂双环[2,2.1]庚基端基的类胡萝卜素。Cycloviolaxanthin的尝试合成（=（3小号，5 - [R，6小号，3'小号，5' - [R，6' - [R）-3,6-：3'，6'-二环氧-5,6,5-'，6' -四氢-β，β-胡萝卜素-5,5'-二醇）
• GMUNDER, MICHAEL ROMAN;EUGSTER, CONRAD HANS, HELV. CHIM. ACTA , 73,(1990) N, C. 1954-1969
  作者：GMUNDER, MICHAEL ROMAN、EUGSTER, CONRAD HANS

  DOI：——

  日期：——
• Chemoenzymatic resolution of cis- and trans-3,6-dihydroxy-α-ionone. Synthesis of the enantiomeric forms of dehydrovomifoliol and 8,9-dehydrotheaspirone
  作者：Stefano Serra、Assem Barakat、Claudio Fuganti

  DOI：10.1016/j.tetasy.2007.10.014

  日期：2007.10

  A straightforward synthesis of both enantiomers of cis- and trans-3-acetoxy-6-hydroxy-alpha-ionone is described. The title compounds are prepared by resolution of the diastereoisomerically pure racemic 3,6-dihydroxy-alpha-ionone isomers. The latter process is based on two steps. The first is the enantio- and regioselective lipase-mediated acetylation of diols to afford the corresponding 3-acetoxy-derivatives. The second is the fractional crystallization of the latter compounds that increase their enantiomeric purity. These building blocks were used for the synthesis of both enantiomeric forms of the natural norterpenoids dehydrovomifoliol 3 and 8,9-dehydrotheaspirone 5. The latter compound is a natural flavor and its odor properties were evaluated by professional perfumers. (c) 2007 Elsevier Ltd. All rights reserved.
• SYNTHESIS AND STEREOCHEMISTRY OF 3,6-EPOXY-5-HYDROXY-5,6-DIHYDRO-β-IONOL, A NOVEL FLAVOR CONSTITUENT OF SUIFU TABACCO
  作者：Tetsuya Kato、Hisao Kondo、Yukishige Kitano、Go Hata、Yoshikazu Takagi

  DOI：10.1246/cl.1980.757

  日期：1980.6.5

  (±)-3,6-Epoxy-5-hydroxy-5,6-dihydro-3-ionol was synthesized from β-ionone via 3,6-dihydroxy-α-ionone and its structure including the relative configurations was established as (±)-2β,5β-epoxy-2α-[3α-hydroxy-1(E)-butenyl]-1β,3,3-trimethylcyclohexan-1α-ol by X-ray analysis.

  (±)-3,6-环氧-5-羟基-5,6-二氢-3-紫罗兰醇是由β-紫罗兰酮通过3,6-二羟基-α-紫罗兰酮合成的，其结构（包括相对构型）确定为（ ±)-2β,5β-环氧-2α-[3α-羟基-1(E)-丁烯基]-1β,3,3-三甲基环己烷-1α-醇，通过 X 射线分析。