(E)-4-(1',6'-Epoxy-2',2',6'-trimethyl-4'-cyclohexen-1'-yl)-3-buten-2-on | 30981-78-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-4-(1',6'-Epoxy-2',2',6'-trimethyl-4'-cyclohexen-1'-yl)-3-buten-2-on
• 英文别名: 3,4-Dehydro-1,2-epoxy-β-jonon；1',2'-Epoxy-dehydro-β-jonon；C13-epoxide；(E)-4-(2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept-4-en-1-yl)but-3-en-2-one
• CAS: 30981-78-3；54685-98-2；75222-70-7；80924-22-7
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: UMKVKAWMASXRPJ-RMKNXTFCSA-N

物化性质

• 沸点：
  277.9±35.0 °C(Predicted)
• 密度：
  1.103±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.65
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  29.6
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (3E)-4-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-3-en-2-one 在 间氯过氧苯甲酸 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 (E)-4-(1',6'-Epoxy-2',2',6'-trimethyl-4'-cyclohexen-1'-yl)-3-buten-2-on
  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

• Synthesis and in vitro characterization of ionone-based compounds as dual inhibitors of the androgen receptor and NF-κB
  作者：Weiguo Liu、Jinming Zhou、Guoyan Geng、Rongtuan Lin、Jian Hui Wu

  DOI：10.1007/s10637-013-0040-y

  日期：2014.4

  Current therapeutic strategy for advanced prostate cancer is to suppress the androgen receptor (AR) signaling. However, lethal castration-resistant prostate cancer (CRPC) arises due to AR reactivation via multiple mechanisms, including mutations in the AR and cross-talk with other pathways such as NF-κB. We have previously identified two ionone-based antiandrogens (SC97 and SC245), which are full antagonists of the wild type and the clinically-relevant T877A, W741C and H874Y mutated ARs. Here, we discovered SC97 and SC245 also inhibit NF-κB. By synthesizing a series of derivatives of these two compounds, we have discovered a novel compound 3b that potently inhibits both AR and NF-κB signalling, including the AR F876L mutant. Compound 3b showed low micromolar antiproliferative activites in C4-2B and 22Rv1 cells, which express mutated ARs and are androgen-independent, as well as DU-145 and PC-3 cells, which exhibit constitutively activated NF-κB signalling. Our studies indicate 3b is effective against the CRPC cells.

  目前晚期前列腺癌的治疗策略是抑制雄激素受体（AR）信号通路。然而，由于AR通过多种机制的再激活，包括AR的突变和与其他通路如NF-κB的交叉作用，致命的去势抵抗性前列腺癌（CRPC）应运而生。我们之前已识别出两种基于伊诺烯的抗雄激素（SC97和SC245），它们是野生型和临床相关的T877A、W741C和H874Y突变AR的完全拮抗剂。在这里，我们发现SC97和SC245也能抑制NF-κB。通过合成这两种化合物的一系列衍生物，我们发现了一种新化合物3b，能够有效抑制AR和NF-κB信号，包括AR F876L突变体。化合物3b在表达突变AR并具雄激素独立性的C4-2B和22Rv1细胞，以及表现为持续激活的NF-κB信号的DU-145和PC-3细胞中显示出低微摩尔的抗增殖活性。我们的研究表明3b对CRPC细胞有效。
• Photochemische Reaktionen. 117. Mitteilung [1] Zur Photochemie von 5,6-Epoxydienen und konjugierten 5,6-Epoxytrienen
  作者：Alex Peter Alder、Hans Richard Wolf、Oskar Jeger

  DOI：10.1002/hlca.19810640122

  日期：1981.2.4

  Photochemistry of 5,6-Epoxydienes and of Conjugated 5,6-Epoxytrienes

  5,6-环氧二烯和共轭5,6-环氧三烯的光化学
• Synthese der (3S,4R,3?S,4?R)- und (3S,4S,3?S,4?S)Crustaxanthine sowie weiterer Verbindungen mit 3,4-Dihydroxy-?-Endgruppen
  作者：Daniel Jacques Buschor、Conrad Hans Eugster

  DOI：10.1002/hlca.19900730426

  日期：1990.6.20

  Synthesis of (3S,4R,3′S,4′R)- and (3S,4S,3′S,4′S)-Crustaxanthins and Further Compounds with 3,4-Dihydroxy β-End-groups

  （3合成小号，4 - [R，3'小号，4' - [R ）-和（3小号，4小号，3'小号，4'小号）-Crustaxanthins并用3,4-二羟基β端基的其它化合物
• Photochemische Reaktionen 113. Mitteilung [1]. Zur Photospaltung konjugierter ?, ?-Epoxyenone: UV.-Bestrahlung von 5, 6-Epoxy-3,4-didehydro-5,6-dihydro-?-jonon
  作者：Kazuo Murato、Hans Richard Wolf、Oskar Jeger

  DOI：10.1002/hlca.19800630811

  日期：1980.12.10

  The Photoinduced Cleavage of Conjugated γ, δ-Epoxyenones: UV.-Irradiation of 5,6-Epoxy-3, 4-didehydro-5,6-dihydro-β-ionone

  共轭的γ，δ-环氧烯酮的光诱导裂解：UV.-辐照5,6-Epoxy-3，4-didehydro-5,6-dihydro-β-紫罗兰酮
• BUSCHOR, DANIEL JACQUES;EUGSTER, CONRAD HANS, VELV. CHIM. ACTA , 73,(1990) N, C. 1002-1021
  作者：BUSCHOR, DANIEL JACQUES、EUGSTER, CONRAD HANS

  DOI：——

  日期：——