10,11-Dihydro-5-ethenyl-5H-dibenzocyclohepten-5-ol | 3241-96-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 二苯并环庚烯
• 英文名称: 10,11-Dihydro-5-ethenyl-5H-dibenzocyclohepten-5-ol
• 英文别名: 5-ethenyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol；5-Hydroxy-5-vinyl-10,11-dihydro-5H-dibenzocyclohepten；5-Hydroxy-5-vinyl-5H-dibenzo-10,11-dihydro-cyclohepten；2-ethenyltricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaen-2-ol
• CAS: 3241-96-1
• 化学式: C₁₇H₁₆O
• 分子量: 236.313
• InChiKey: SFCXNAUHZCZAGE-UHFFFAOYSA-N

物化性质

• 沸点：
  357.0±41.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  10,11-Dihydro-5-ethenyl-5H-dibenzocyclohepten-5-ol 在 碘 、 silver(I) acetate 作用下， 以 乙醇 、 甲苯 、 苯 为溶剂， 反应 5.5h， 生成 6-Methylene-5,6,11,12-tetrahydrodibenzocycloocten-5-one
  参考文献：
  名称：

  .beta.-Iodo Ketones by Prevost Reaction Of Vinyl Carbinols

  摘要：

  Treatment of alpha-ethenyl-alpha-phenylbenzenemethanol with iodine and silver acetate in either acetic acid or benzene gave 1,2-diphenyl-3-iodo-1-propanone (6) in 85% yield. Ring enlargements involving similar rearrangements were observed with a number of cyclic vinyl carbinols. In some cases, mixtures of normal Prevost products and rearranged beta-iodo ketones were obtained. The exact scope of this apparently novel reaction remains to be elucidated. Treatment of the beta-iodo ketones with DBU gave the corresponding alpha,beta-unsaturated ketones from which a number of amino ketones and amino alcohols were prepared by conjugate addition followed by reduction.

  DOI：

  10.1021/jo00119a021
• 作为产物：
  描述：

  10,11-二氢二苯并[a,b]环庚烯-5-酮 、 乙烯基溴化镁 以 四氢呋喃 为溶剂， 生成 10,11-Dihydro-5-ethenyl-5H-dibenzocyclohepten-5-ol
  参考文献：
  名称：

  三氟乙酸促进烯丙醇硫氰化

  摘要：

  在无金属和氧化剂的条件下，使用烯丙醇作为底物和易于获得的 NH 4 SCN 作为硫氰酸盐源，提出了一种快速有效的酸促进策略来获得烯丙基硫氰酸盐。在这个温和的反应体系中可以容忍各种叔和仲烯丙醇。

  DOI：

  10.1002/ejoc.202300148

文献信息

• Divergent Synthesis of Trifluoromethyl Sulfoxides and β-SCF₃ Carbonyl Compounds by Tandem Trifluoromethylthiolation/Rearrangement of Allylic and Propargylic Alcohols
  作者：Deng Zhu、Tong-Mei Ding、Hui-Yun Luo、Hua Ke、Zhi-Min Chen

  DOI：10.1021/acs.orglett.0c02875

  日期：2020.10.2

  A selenium-catalyzed trifluoromethylthiolation/[2,3]-sigmatropic rearrangement of tertiary allylic and propargylic alcohols which could provide straightforward and facile access to trifluoromethyl sulfoxides was developed. Various allylic and allenic trifluoromethyl sulfoxides were obtained with moderate to excellent yields. Meanwhile, a Lewis acid mediated trifluoromethylthiolation/1,2-rearrangement

  开发了硒催化的三烯丙基和丙炔醇的三氟甲基硫醇化/ [2,3]-σ重排，可提供直接而又容易获得的三氟甲基亚砜。获得各种烯丙基和烯丙基三氟甲基亚砜，具有中等至优异的产率。同时，路易斯酸介导的trifluoromethylthiolation / 1,2-重排合成β-SCF 3的羰基化合物也已实现。这两个串联反应的特征是反应条件温和且不含金属。在这两个反应中，揭示了亲电三氟甲基硫醇化的化学选择性。
• Selenium-Catalyzed Trifluoromethylsulfinylation/Rearrangement of Allylic and Propargylic Alcohols: Access to Allylic and Allenic Triflones
  作者：Deng Zhu、Hui-Yun Luo、Zhi-Min Chen

  DOI：10.1021/acs.orglett.0c04236

  日期：2021.2.5

  A selenium-catalyzed trifluoromethylsulfinylation/rearrangement of allylic and propargylic alcohols for synthesizing triflones was developed for the first time. Various allylic and allenic triflones were delivered in moderate to excellent yields. After numerous control experiments were performed, it was suggested that this transformation includes an unusual [+SCF3] group disproportionation process

  首次开发了硒催化的三氟甲基亚磺酰基化/烯丙基和炔丙基醇的重排反应，用于合成三氟甲磺酸。各种烯丙基和艾伦三烯酮以中等至优异的产率递送。经过大量的控制实验后，有人认为这种转变包括一个不寻常的[ + SCF 3 ]基歧化过程，该过程形成了硒原位催化的[ + SOCF 3 ]，H 2 O被用作氧资源。该反应具有温和的反应条件和良好的底物相容性，并且不含过渡金属。
• I2/Li2CO3-promoted cyanation of diarylalcohols through a dual activation process
  作者：Liangzhen Hu、Muhammad Ijaz Hussain、Qingfu Deng、Qing Liu、Yangyang Feng、Xiaohui Zhang、Yan Xiong

  DOI：10.1016/j.tet.2018.11.069

  日期：2019.1

  One-step base promoted strategy for cyanation of α,α-diaryl alcohols has been developed under mild and transition metal-free conditions. This method provides a straightforward and facile way towards the synthesis of β,γ-unsaturated nitriles and α-phenylnitiriles from α-vinyl carbinols and α,α-diaryl methanols, respectively, up to 99% yield. Moreover, various azides and ethers could also be accessed

  在温和且无过渡金属的条件下，已经开发出了一步法促进α，α-二芳基醇氰化的策略。该方法为直接从α-乙烯基甲醇和α，α-二芳基甲醇合成β，γ-不饱和腈和α－苯基腈提供了一种直接而又简便的方法，产率高达99％。此外，在标准反应条件下，还可从它们各自的亲核试剂中获得各种叠氮化物和醚。
• N-substituted azaheterocyclic carboxylic acids
  申请人：Novo Nordisk A/S

  公开号：US05348965A1

  公开（公告）日：1994-09-20

  The invention relates to therapeutically active azaheterocyclic compounds and to pharmaceutical compositions comprising the compounds. The novel compounds are useful in treating a central nervous system ailment related to the GABA uptake.

  这项发明涉及治疗活性的氮杂杂环化合物以及包含这些化合物的药物组合物。这些新型化合物在治疗与GABA摄取有关的中枢神经系统疾病方面是有用的。
• Synthesis of Novel γ-Aminobutyric Acid (GABA) Uptake Inhibitors. 5. Preparation and Structure−Activity Studies of Tricyclic Analogues of Known GABA Uptake Inhibitors
  作者：Knud Erik Andersen、Jan L. Sørensen、Jesper Lau、Behrend F. Lundt、Hans Petersen、Per O. Huusfeldt、Peter D. Suzdak、Michael D. B. Swedberg

  DOI：10.1021/jm990513k

  日期：2001.6.1

  On the basis of the SAR of a series of known gamma-aminobutyric acid (GABA) uptake inhibitors, including 4 (SKF 89976), new tricyclic analogues have been prepared. These novel compounds are derivatives of nipecotic acid, guvacine, and homo-beta-proline, substituted at the nitrogen of these amino acids by various lipophilic moieties such as (10,11-dihydro-5H-dibenz[b,f]azepin-5-yl)alkoxyalkyl or (10

  基于一系列已知的γ-氨基丁酸（GABA）摄取抑制剂（包括4种（SKF 89976））的SAR，已制备了新的三环类似物。这些新颖的化合物是乳香酸，番石榴碱和高β-脯氨酸的衍生物，在这些氨基酸的氮上被各种亲脂性部分所取代，例如（10,11-dihydro-5H-dibenz [b，f] azepin-5 -基）烷氧基烷基或（10,11-二氢-5H-二苯并[a，d]环庚基-5-亚烷基）烷氧基烷基。确定了该新系列中每种化合物抑制大鼠突触小体中[（3）H] -GABA吸收的体外值，并且发现几种新型化合物显示出与参考化合物相当的高效价4、5（替加滨）和6（CI-966）。还评估了几种新型化合物的体内抑制15 mg / kg（ip）剂量的6,7-二甲氧基-4-乙基-β-咔啉-3-羧酸甲酯（DMCM）诱发的阵挛性癫痫发作的能力。 。一种化合物是（R）-1-（2-（2-（2-（10,11-二氢-5H-二苯并[b，f]