5-hydroxy-5-phenyl-10,11-dihydrodibenzo[a,d]cycloheptene | 55090-32-9

• 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: 5-hydroxy-5-phenyl-10,11-dihydrodibenzo[a,d]cycloheptene
• 英文别名: 5-phenyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol；5-phenyl-10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-ol；5-phenyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol；10,11-dihydro-5-phenyl-5H-dibenzo[a,d]cyclohepten-5-ol；5-Phenyl-10,11-dihydro-5H-dibenzo(A,D)cyclohepten-5-OL；2-phenyltricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaen-2-ol
• CAS: 55090-32-9
• 化学式: C₂₁H₁₈O
• 分子量: 286.373
• InChiKey: CAIIMJUORNLXOK-UHFFFAOYSA-N

物化性质

• 熔点：
  151 °C
• 沸点：
  423.9±14.0 °C(Predicted)
• 密度：
  1.176±0.06 g/cm3(Predicted)
• 保留指数：
  2415

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  5-hydroxy-5-phenyl-10,11-dihydrodibenzo[a,d]cycloheptene 在 硫酸 、 双氧水 、 溶剂黄146 作用下， 以46%的产率得到10,11-二氢二苯并[a,b]环庚烯-5-酮
  参考文献：
  名称：

  Taljaard, Benjamin; Goosen, Andre; McCleland, Cedric W., Journal of the Chemical Society. Perkin transactions I, 1989, p. 931 - 934

  摘要：

  DOI：
• 作为产物：
  描述：

  10,11-二氢二苯并[a,b]环庚烯-5-酮 以49%的产率得到
  参考文献：
  名称：

  TALIAARD, BENJAMIN;GOOSEN, ANDRE;MCCLELAND, CEDRIC W., J. CHEM. SOC. PERKIN TRANS. PT 1,(1989) N, C. 931-934

  摘要：

  DOI：

文献信息

• Tricylic amino-acid derivatives
  申请人：Allelix Neuroscience Inc.

  公开号：US06162824A1

  公开（公告）日：2000-12-19

  Described herein are compounds which have the general formula: ##STR1## or a prodrug or pharmaceutically acceptable salt, solvate or hydrate thereof wherein: R.sup.1 is selected from the group consisting of H, alkyl and the counter ion for a basic addition salt; X is selected from the group consisting of CR.sup.9 R.sup.10, S, O, SO, SO.sub.2, NH and N-alkyl; R.sup.2, R.sup.3, R.sup.4, R.sup.9 and R.sup.10 are independently selected from the group consisting of H and alkyl; R.sup.5 and R.sup.6 are independently selected from the group consisting of H, alkyl and phenyl, or, alternatively, R.sup.5 and R.sup.6 together may form a methylene group or a 3- to 6-membered a spirocyclic group; wherein, when X is CR.sup.9 R.sup.10, one or both pairs of R.sup.5 and R.sup.9 or R.sup.6 and R.sup.10 may join to form a double or triple bond R.sup.7 is selected from the group consisting of Formula II-V: ##STR2## which are all optionally substituted, at nodes other than R.sup.8, with 1-4 substituents independently selected from the group consisting of alkyl, halo, aryl (which may be substituted as for R.sup.8), trifluoromethyl, trifluoromethoxy, nitro, cyano, amino, mono-alkylamino, di-alkylamino, alkoxycarbonyl, alkylcarbonyl, alkoxythiocarbonyl, alkylthiocarbonyl, alkoxy, alkylS-, phenoxy, --SO.sub.2 NH.sub.2, --SO.sub.2 NHalkyl, --SO.sub.2 N(alkyl).sub.2 and 1,2-methylenedioxy; and wherein any of the benzo-fused rings in structures II to V may be replaced by a 5- or 6-membered heterocyclic ring selected from the group consisting of pyridine, thiophene, furan and pyrrole; wherein R.sup.8 is selected from the group consisting of H, alkyl, benzyl, cycloalkyl, indanyl and an optionally substituted aryl group, wherein the optional substituents are independently selected from 1-4 members of the group consisting of alkyl, halo, aryl, trifluoromethyl, trifluoromethoxy, nitro, cyano, amino, mono-alkylamino, di-alkylamino, alkoxycarbonyl, alkylcarbonyl, alkoxythiocarbonyl, alkylthiocarbonyl, alkoxy, alkylS-, phenoxy, --SO.sub.2 NH.sub.2, --SO.sub.2 NHalkyl, --SO.sub.2 N(alkyl).sub.2 and 1,2-methylenedioxy; --represents a single or double bond; Y is selected from the group consisting of O, S, SO, NH, N-alkyl, CH.sub.2, CH-alkyl, C(alkyl).sub.2, and C.dbd.O; Z is selected from the group consisting of CH.sub.2, O, S, NH and N-alkyl when--is a single bond; Z is selected from the group consisting of CH and N when--is a double bond. Also described is the use of these compounds as pharmaceuticals.

  本文描述了具有以下一般式的化合物：##STR1##或其前药或药用可接受的盐、溶剂或水合物，其中：R.sup.1选自H、烷基和碱性加成盐的对离子组成的群；X选自CR.sup.9 R.sup.10、S、O、SO、SO.sub.2、NH和N-烷基的群；R.sup.2、R.sup.3、R.sup.4、R.sup.9和R.sup.10独立地选自H和烷基的群；R.sup.5和R.sup.6独立地选自H、烷基和苯基，或者，作为另一选择，R.sup.5和R.sup.6可以一起形成亚甲基基团或3-至6-成员的螺环基团；当X为CR.sup.9 R.sup.10时，R.sup.5和R.sup.9或R.sup.6和R.sup.10中的一个或两个对可能连接以形成双键或三键R.sup.7选自以下式II-V的群：##STR2##它们都可以在除R.sup.8之外的节点上选择性地取代，取代基独立地选自烷基、卤素、芳基（可能像R.sup.8那样被取代）、三氟甲基、三氟甲氧基、硝基、氰基、氨基、单烷基氨基、双烷基氨基、烷氧羰基、烷基羰基、烷氧硫代羰基、烷基硫代羰基、烷氧基、烷基硫、苯氧基、--SO.sub.2 NH.sub.2、--SO.sub.2 NH烷基、--SO.sub.2 N(烷基).sub.2和1,2-亚甲二氧基；结构II至V中的苯并环中的任何一个都可以被选择自吡啶、噻吩、呋喃和吡咯的5-或6-成员杂环环取代；其中R.sup.8选自H、烷基、苄基、环烷基、茚基和一个可选择性取代的芳基，其中可选择性取代基独立地选自烷基、卤素、芳基、三氟甲基、三氟甲氧基、硝基、氰基、氨基、单烷基氨基、双烷基氨基、烷氧羰基、烷基羰基、烷氧硫代羰基、烷基硫代羰基、烷氧基、烷基硫、苯氧基、--SO.sub.2 NH.sub.2、--SO.sub.2 NH烷基、--SO.sub.2 N(烷基).sub.2和1,2-亚甲二氧基；--表示单键或双键；Y选自O、S、SO、NH、N-烷基、CH.sub.2、CH-烷基、C(烷基).sub.2和C.dbd.O的群；当--为单键时，Z选自CH.sub.2、O、S、NH和N-烷基的群；当--为双键时，Z选自CH和N的群。还描述了这些化合物作为药物的用途。
• Structure-Guided Design of Novel <scp>l</scp>-Cysteine Derivatives as Potent KSP Inhibitors
  作者：Naohisa Ogo、Yoshinobu Ishikawa、Jun-ichi Sawada、Kenji Matsuno、Akihiro Hashimoto、Akira Asai

  DOI：10.1021/acsmedchemlett.5b00221

  日期：2015.9.10

  previously reported S-trityl-l-cysteine derivatives as selective KSP inhibitors. Here, we report further optimizations using docking modeling in the L5 allosteric binding site, which led to the discovery of several high affinity derivatives with two fused phenyl rings in the trityl group giving low nanomolar range KSP ATPase inhibition. The representative derivatives potently inhibited cell growth of HCT116

  驱动蛋白纺锤体蛋白（KSP），称为Hs Eg5，是驱动蛋白5家族的成员，在双极纺锤体的形成和维持中起着重要作用。我们先前报道了S-三苯甲基-1-半胱氨酸衍生物作为选择性KSP抑制剂。在这里，我们报告了在L5变构结合位点使用对接模型的进一步优化，这导致了在三苯甲基中具有两个稠合苯环的几种高亲和力衍生物的发现，从而产生了低纳摩尔范围的KSP ATPase抑制作用。代表性衍生物在体内与KSP抑制活性相关地有效抑制HCT116细胞的细胞生长，并显着抑制肿瘤生长。
• N, N′ — Ditritylurea and Analogs as Hosts in Crystalline Clathrate Complexes: Synthesis and Selectivity Studies
  作者：Kwok-Keung Daniel Ng、Harold Hart

  DOI：10.1016/0040-4020(95)00432-8

  日期：1995.7

  Of 38 hosts, most of them new, designed on the ‘wheel-and-axle’ model, 24 formed clathrate complexes with small molecules; 95 new host/guest combinations are described (Table 6). Selectivity studies (Table 7) show, in some instances, substantial discrimination between guests with similar structures.

  在38个宿主（其中大多数是新宿主）中，它们是按照“轮轴”模型设计的，其中24个形成了具有小分子的笼形复合物。描述了95种新的主机/来宾组合（表6）。选择性研究（表7）显示，在某些情况下，具有相似结构的客人之间存在明显的区别。
• Functionalized Triarylcarbenium Ions as Catalysts in Mukaiyama Aldol Addition: Effects of Counter Ions and Silyl Groups on the Intervention of Silyl Catalysis
  作者：Chien-Tien Chen、Shi-Deh Chao、Kuao-Chung Yen

  DOI：10.1055/s-1998-1815

  日期：1998.8

  Stereochemical studies have indicated that functionalized Tr+SbCl6 - may serve as efficient aldol reaction catalysts by judicious choice of a silyl component. The aldol addition between TMS ketene acetal derived from γ-butyrolactone and benzaldehyde provided the silyl aldolates with high syn diastereoselectivities.

  立体化学研究表明，通过明智地选择硅基成分，官能化的 Tr+SbCl6 - 可作为高效的醛醇反应催化剂。从δ-丁内酯衍生的 TMS 烯酮缩醛与苯甲醛之间的醛加成反应提供了具有高同步非对映选择性的硅烷醛酸酯。
• Triarylcarbenium ions as catalysts in the Mukaiyama Aldol addition: A mechanistic investigation
  作者：Scott E. Denmark、Chien-Tien Chen

  DOI：10.1016/s0040-4039(00)73345-4

  日期：1994.6

  1-Phenyl-2:3,6:7-dibenzosuberyl salts 5+ efficiently catalyze the aldol reaction between silyl enol ethers and benzaldehyde with moderate diastereoselectivity. Crossover experiments with doubly labeled silyl enol ethers, kinetic and stereochemical studies identify 5+ as the catalyst rather than a Lewis acidic R3SiX species in this transformation.

  1-苯基-2：3,6：7-二苯并亚戊基盐5 +以中等的非对映选择性有效催化甲硅烷基烯醇醚与苯甲醛之间的羟醛反应。使用双标记的甲硅烷基烯醇醚的交叉实验，动力学和立体化学研究确定了5 +作为催化剂，而不是路易斯酸性R 3 SiX物种。