rac-(1R,6R)-bicyclo[4.2.0]oct-3-en-7-one | 57774-82-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: rac-(1R,6R)-bicyclo[4.2.0]oct-3-en-7-one
• 英文别名: bicyclo[4.2.0]oct-3-en-7-one；rel-(1R,6R)-Bicyclo[4.2.0]oct-3-en-7-one；(1S,6S)-bicyclo[4.2.0]oct-3-en-7-one
• CAS: 57774-82-0
• 化学式: C₈H₁₀O
• 分子量: 122.167
• InChiKey: AYXQRXAAJYZWJJ-BQBZGAKWSA-N

物化性质

• 沸点：
  202.8±29.0 °C(Predicted)
• 密度：
  1.083±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  rac-(1R,6R)-bicyclo[4.2.0]oct-3-en-7-one 在 双氧水 作用下， 以 水 、 溶剂黄146 为溶剂， 以95%的产率得到3a,4,7,7a-tetrahydro-1-benzofuran-2(3H)-one
  参考文献：
  名称：

  Synthesis and absolute configuration of phyllanthurinolactone, the leaf-closing factor of a nyctinastic plant, Phyllanthus urinaria L.

  摘要：

  Phyllanthurinolactone (1) and its diastereoisomer 19 were synthesized, only the former of which was bioactive as the leaf-closing factor of Phyllanthus urinaria L. X-ray analysis of the tetraacetylglucoside 18 was executed, and the absolute configuration of 1 was determined as 6S, 7aR. (C) 1997, Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(96)02375-1
• 作为产物：
  描述：

  1,4-环己二烯 在 溶剂黄146 、 锌 作用下， 以 乙醚 为溶剂， 生成 rac-(1R,6R)-bicyclo[4.2.0]oct-3-en-7-one
  参考文献：
  名称：

  新型卤素分子；合成，结构阐明，机理和抗氧化活性

  摘要：

  在这项研究中，从乙烯酮加成反应中合成了可能具有生物学重要性的卤代环氧，卤代酮，卤代内酯，卤代醛和卤代醇。分子的结构通过NMR，特别是COZY光谱法照明。此外，还使用了FT-IR和GC-MS技术。在进行合成时，我们意外地遇到了准Favorskii排列积。进行X射线分析以确定该分子的确切结构。此外，还研究了一些分子的抗氧化特性，并将其与标准品（BHT，BHA和α-生育酚）进行了比较。 图形摘要

  DOI：

  10.1007/s00706-021-02746-2

文献信息

• α‐Arylation and Ring Expansion of Annulated Cyclobutanones: Stereoselective Synthesis of Functionalized Tetralones
  作者：Stanley Chang、Michael Holmes、Jeffrey Mowat、Michael Meanwell、Robert Britton

  DOI：10.1002/anie.201608449

  日期：2017.1.16

  α‐Arylcyclobutanones display unique reactivity that makes them valuable synthetic intermediates and target molecules. We describe the preparation of α‐aryl‐ and α‐heteroarylcyclobutanones through a direct α‐arylation reaction. Problematic fragmentations are avoided by the use of LiOtBu, which promotes a rapid but reversible self‐aldol reaction that slowly releases the enolate required for α‐arylation

  α-芳基环丁酮显示出独特的反应活性，使其成为有价值的合成中间体和目标分子。我们描述了通过直接的α-芳基化反应制备α-芳基和α-杂芳基环丁酮的方法。通过使用LiO t Bu避免了有问题的碎片化，LiO t Bu可以促进快速但可逆的自我羟醛反应，从而缓慢释放α芳构化所需的烯醇化物。我们还展示了α-芳基环丁酮的环扩展，该过程在1-甲氧基硫代甲状腺素D的立体选择性合成中得到了突出显示。
• Study on structure-activity relationship (SAR) of simplified mirogabalin derivatives as voltage-gated calcium channel α2δ ligands for the treatment of chronic neuropathic pain
  作者：Yuanwen Zhang、Yueming Zheng、Qingqing Wu、Fuyun Tian、Chuanjun Ma、Haiyan Xu、Li Zhan、Zhaobing Gao、Guilong Zhao、Huihui Ti

  DOI：10.1007/s00044-022-03006-6

  日期：2023.2

  subunit ligands (gabapentinoids), we designed and synthesized 11 bicyclic and monocyclic derivatives based on mirogabalin, a third-generation VGCC α2δ subunit ligand. The competitive binding of the synthesized compounds to the human VGCC α2δ-1 subunit was measured in vitro, and the results demonstrated that the lipophilic moiety size was strictly limited in gabapentinoids, in which conformationally rigid

  迫切需要针对慢性神经性疼痛的临床治疗，电压门控钙通道 (VGCC) α2δ 亚基是最有希望的治疗靶点之一。为了深入探索 VGCC α2δ 亚基配体（加巴喷丁类）中亲脂部分的构效关系 (SAR)，我们设计并合成了 11 种基于第三代 VGCC α2δ 亚基配体米罗巴林的双环和单环衍生物。在体外测量了合成化合物与人 VGCC α2δ-1 亚基的竞争性结合，结果表明加巴喷丁类化合物的亲脂性部分大小受到严格限制，其中构象刚性的双环 [3.2.0] 庚烷/庚烯具有顺式-融合是最优选的结构。相反，单环环丁烷与显着降低的结​​合亲和力相关，除了4 (IC 50  = 15.2 nM)，其中取代基可以模拟双环[3.2.0]庚烷/庚烯的刚性构象；亲脂性部分中的杂原子不利于结合亲和力 ( 2，IC 50  > 729 nM)。本研究中获得的 SAR 发现对于设计新型加巴喷丁类药物以治疗未来的慢性神经性疼痛具有重要意义。
• Stereoselective synthesis of deoxycarbaheptopyranose derivatives: 5a-carba-6-deoxy-α-dl-galacto-heptopyranose and 5a-carba-6-deoxy-α-dl-gulo-heptopyranose
  作者：Nurhan Horasan Kishali、Dilem Doğan、Ertan Şahin、Aslihan Gunel、Yunus Kara、Metin Balci

  DOI：10.1016/j.tet.2010.11.102

  日期：2011.2

  Two new deoxycarbaheptopyranoses, 5a-carba-6-deoxy-alpha-DL-galacto-heptopyranose and 5a-carba-6-deoxy-alpha-DL-gulo-heptopyranose were prepared starting from cyclohexa-1,4-diene. The addition of dichloroketene to cyclohexa-1,4-diene followed by the subsequent reductive elimination and Baeyer-Villiger oxidation in turn led to the formation of a bicyclic lactone. Reduction of the lactone moiety followed by acetylation gave a diacetate with cis-configuration. The introduction of additional acetate functionality into the molecule was achieved by singlet oxygen ene-reaction. The formed hydroperoxide was reduced and then acetylated. The triacetate was further functionalized either by direct cis-hydroxylation using OsO4 or by epoxidation followed by a ring-opening reaction to give the title heptopyranose derivatives. One of the synthesized molecules, galacto-heptopyranose exhibited enzyme specific inhibition against alpha-glycosidase. On the other hand, they did not show any inhibition for alpha-amylase. However, both compounds, gulo-heptopyranose and galacto-heptopyranose increased the activity of alpha-amylase. (C) 2010 Elsevier Ltd. All rights reserved.
• Unusual Facial Selectivity in the Cycloaddition of Singlet Oxygen to a Simple Cyclic Diene¹
  作者：Kelly M. Davis、Barry K. Carpenter

  DOI：10.1021/jo9604292

  日期：1996.1.1

  Syntheses of 5-isopropyl-1,3-cyclohexadiene and syn-5-isopropyl-2,3-dioxabicyclo[2.2.2]octane, by routes that would allow completely diastereoselective introduction of deuterium labels, are described. The reaction of the isopropyl cyclohexadiene with singlet oxygen is shown to give an endoperoxide that is derived by preferential attack on the more sterically hindered face of the diene, A possible mechanistic explanation of this result is that the attack from the less hindered face leads to ''ene'' reaction rather than endoperoxide formation, However, this mechanism would require that the ''ene'' reaction and cycloaddition proceed via a common intermediate-presumably a perepoxide.
• Synthesis and absolute configuration of phyllanthurinolactone, the leaf-closing factor of a nyctinastic plant, Phyllanthus urinaria L.
  作者：Kenji Mori、Gérard Audran、Yoshiaki Nakahara、Masahiko Bando、Masaru Kido

  DOI：10.1016/s0040-4039(96)02375-1

  日期：1997.1

  Phyllanthurinolactone (1) and its diastereoisomer 19 were synthesized, only the former of which was bioactive as the leaf-closing factor of Phyllanthus urinaria L. X-ray analysis of the tetraacetylglucoside 18 was executed, and the absolute configuration of 1 was determined as 6S, 7aR. (C) 1997, Elsevier Science Ltd. All rights reserved.