1-hydroxy-3-phenylcyclopent-2-ene | 19926-46-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-hydroxy-3-phenylcyclopent-2-ene
• 英文别名: 3-phenylcyclopent-2-en-1-ol；3-Phenyl-2-cyclopentenol
• CAS: 19926-46-6
• 化学式: C₁₁H₁₂O
• 分子量: 160.216
• InChiKey: OFUCNPVOTCEASP-UHFFFAOYSA-N

物化性质

• 沸点：
  288.4±40.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-hydroxy-3-phenylcyclopent-2-ene 在 palladium on activated charcoal 咪唑 、 4 A molecular sieve 、 porcine pancrease lipase 、 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 (+)-(1R,3S)-3-phenylcyclopentyl acetate
  参考文献：
  名称：

  3-苯基环戊醇衍生物的两种对映异构体的高效合成

  摘要：

  通过在有机介质中通过脂肪酶催化的酯交换反应（动力学拆分），可以实现3-（取代的苯基）环戊醇各自旋光异构体的高效，多克级合成。通过化学收率和对映选择性测量，该酶促反应以很高的效率进行。外消旋的顺式醇3被成功拆分，得到（1 R，3 S）-乙酸7和相应的（1 S，3 R）-醇3。通过生物活性化合物的实际合成证明了该方法的实用性。（1 R，3 S）-乙酸盐7将（1 S，3 R）-醇3和（1 S，3 R）-醇3分别转化为口服活性5-脂氧合酶抑制剂，而不会损失光学纯度。

  DOI：

  10.1016/s0040-4020(02)01090-6
• 作为产物：
  描述：

  4-[(tert-butyldimethylsilyl)oxy]cyclopent-2-enone 在 sodium tetrahydroborate 、 copper(l) iodide 、 四溴化碳 、 四丁基氟化铵 、 双氧水 、 silver trifluoroacetate 、 L-Selectride 、 三苯基膦 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 20.58h， 生成 1-hydroxy-3-phenylcyclopent-2-ene
  参考文献：
  名称：

  Formation of 1-phenyl-2,3-dioxabicyclo[2.2.1]heptane in the reaction of 1,3-dibromo-4-phenylcyclopentane with hydrogen peroxide in the presence of silver trifluoroacetate

  摘要：

  DOI：

  10.1021/jo00248a035

文献信息

• 1,<i>n</i>-Rearrangement of Allylic Alcohols Promoted by Hot Water: Application to the Synthesis of Navenone B, a Polyene Natural Product
  作者：Pei-Fang Li、Heng-Lu Wang、Jin Qu

  DOI：10.1021/jo5004086

  日期：2014.5.2

  n-rearrangement (n = 3, 5, 7, 9) of allylic alcohols. In some cases, the rearrangement reactions joined isolated C–C double or triple bonds to generate conjugated polyene or enyne structure motifs. We used the 1,3-rearrangement reaction of an allylic alcohol in hot water as part of an attractive new strategy for construction of the polyene natural product navenone B by iterative use of a Grignard reaction

  首次报道，作为弱酸性催化剂的热水有效地促进了烯丙醇的1，n重排（n = 3、5、7、9 ）。在某些情况下，重排反应会连接孤立的C双键或C键，从而生成共轭多烯或烯结构的基序。我们使用了烯丙醇在热水中的1,3-重排反应作为通过反复使用格利雅（Grignard）反应构建多烯天然产物navenone B的有吸引力的新策略的一部分，将所得烯丙基的1,3-重排酒精和随后氧化的重排产物。
• Novel Arylbicyclo[3.1.0]Hexylamines And Methods And Compositions For Their Preparation And Use
  申请人：Skolnick Phil

  公开号：US20080194696A1

  公开（公告）日：2008-08-14

  The invention provides novel arylbicyclo[3.1.0]hexylamines, and related processes and intermediates for preparing these compounds, as well as compositions and methods employing these compounds for the treatment and/or prevention of central nervous system (CNS) disorders, including but not limited to depression and anxiety.

  本发明提供了新型芳基双环[3.1.0]己基胺，以及制备这些化合物的相关过程和中间体，以及使用这些化合物的组合物和方法，用于治疗和/或预防中枢神经系统（CNS）疾病，包括但不限于抑郁症和焦虑症。
• Palladium-Catalyzed Borylative Cyclization and Cyclopropanation of Terminal Alkyne-Derived Enynes
  作者：Duhao Sun、Bing Zhou、Lanqin Liu、Xiaoyun Chen、Hong Hou、Ying Han、Chaoguo Yan、Yaocheng Shi、Shaoqun Zhu

  DOI：10.1021/acs.orglett.3c01551

  日期：2023.6.30

  Described herein is a palladium-catalyzed borylative cyclization and cyclopropanation of terminal alkyne-derived enynes, affording borylated bicycles, fused cycles, and bridged cycles in good isolated yields. The synthetic utility of this protocol was fully demonstrated by large scale reaction and synthetic derivatization of the borate group.

  本文描述的是末端炔衍生的烯炔的钯催化的硼化环化和环丙烷化，以良好的分离收率提供硼化双环、稠合环和桥环。通过硼酸基团的大规模反应和合成衍生化，充分证明了该方案的合成实用性。
• Mild and Tunable Benzoic Acid Catalysts for Rearrangement Reactions of Allylic Alcohols
  作者：J. Adam McCubbin、Samantha Voth、Oleg V. Krokhin

  DOI：10.1021/jo201540p

  日期：2011.10.21

  An efficient and simple catalytic method for the isomerization of readily prepared allylic alcohols is described. We focus particularly on cyclic examples and the synthesis of unusual enyne and dienols. The benzoic acid catalysts employed are commercially available and very inexpensive and can be tuned for reactivity and substrate sensitivity.
• Discovery of Orally Efficacious Melanin-Concentrating Hormone Receptor-1 Antagonists as Antiobesity Agents. Synthesis, SAR, and Biological Evaluation of Bicyclo[3.1.0]hexyl Ureas
  作者：Mark D. McBriar、Henry Guzik、Sherry Shapiro、Jaroslava Paruchova、Ruo Xu、Anandan Palani、John W. Clader、Kathleen Cox、William J. Greenlee、Brian E. Hawes、Timothy J. Kowalski、Kim O'Neill、Brian D. Spar、Blair Weig、Daniel J. Weston、Constance Farley、John Cook

  DOI：10.1021/jm050886n

  日期：2006.4.1

  Melanin-concentrating hormone (MCH) is a cyclic, nonadecapeptide expressed in the CNS of all vertebrates that regulates feeding behavior and energy homeostasis via interaction with the central melanocortin system. Regulation of this interaction results in modulation of food intake and body weight gain, demonstrating significant therapeutic potential for the treatment of obesity. The MCH-1 receptor (MCH-R1) has been identified as a key target in MCH regulation, as small molecule antagonists of MCH-R1 have demonstrated activity in vivo. Herein, we document our research in a bicyclo[3.1.0]hexyl urea series with particular emphasis on structure-activity relationships and optimization of receptor occupancy, measured both in vitro and via an ex vivo binding assay following an oral dosing regimen. Several compounds have been tested in vivo and exhibit oral efficacy in relevant acute rodent feeding models. In particular, 24u has proven efficacious in chronic rodent models of obesity, showing a statistically significant reduction in food intake and body weight over a 28 day study.