2-(2,2-diphenylcyclopropyl)ethanol | 38674-45-2

• 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: 2-(2,2-diphenylcyclopropyl)ethanol
• 英文别名: β-(gem.-Diphenylcyclopropyl)ethanol；2-(2',2'-Diphenyl-cyclopropyl)-aethanol；Cyclopropaneethanol, 2,2-diphenyl-
• CAS: 38674-45-2
• 化学式: C₁₇H₁₈O
• 分子量: 238.329
• InChiKey: YUYSIBOARIIHOF-UHFFFAOYSA-N

物化性质

• 沸点：
  369.1±11.0 °C(Predicted)
• 密度：
  1.107±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  2-(2,2-diphenylcyclopropyl)ethanol 在 吡啶 、 sodium acetate 作用下， 生成 β-(gem.-Diphenylcyclopropyl)ethyl-acetat
  参考文献：
  名称：

  3,3-Diaryltricyclo[3.2.1.02,4]octanes. III. Solvolysis pathway for exo-3,3-diaryltricyclo[3.2.1.02,4]oct-exo-6-yl tosylates

  摘要：

  DOI：

  10.1021/jo00919a031
• 作为产物：
  描述：

  3-乙氧基羰基-4,4-二苯基-3-丁酸 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 以77%的产率得到2-(2,2-diphenylcyclopropyl)ethanol
  参考文献：
  名称：

  Structure-activity studies on benzhydrol-containing nipecotic acid and guvacine derivatives as potent, orally-active inhibitors of GABA uptake

  摘要：

  The introduction of lipophilic groups onto the ring nitrogen of nipecotic acid and guvacine, two known GABA uptake inhibitors, afforded potent, orally-active anticonvulsant drugs. A series of compounds is reported which explores the structure-activity relationships (SAR) in this series. Among the areas explored: side-chain SAR (aromatic-, heterocyclic-, and tricyclic-containing side chains) and modifications to the tetrahydropyridine ring. The benzhydrol ether-containing side chains afforded the most potent compounds with several exhibiting in vitro IC50 values for GABA uptake of <1 muM (including 5, Table 1; 37, 43, Table IV; and 44, Table V). Compound 44 was selected for extensive evaluation and subsequently progressed to Phase 1 clinical trials with severe adverse effects seen after single dose administration to humans.

  DOI：

  10.1021/jm00100a032

文献信息

• <i>p</i>-Nitrobenzenesulfenate Esters as Precursors for Laser Flash Photolysis Studies of Alkyl Radicals
  作者：Martin Newcomb、Pierre Daublain、John H. Horner

  DOI：10.1021/jo026218g

  日期：2002.11.1

  laser flash photolysis (LFP) studies to generate alkoxyl radicals that fragmented to give the (2,2-diphenylcyclopropyl)methyl radical. Rate constants for the beta-scission reactions increased as a function of the carbonyl compound produced in the fragmentation reaction in the order CH2O < MeCHO < Me2CO < PhCHO < Ph2CO and increased with increasing solvent polarity. For alkoxyl radicals that fragment

  在激光闪光光解（LFP）研究中使用了一系列对硝基苯磺酸酯，以生成烷氧基基团，这些基团碎裂后得到（2,2-二苯基环丙基）甲基基团。β断裂反应的速率常数随裂解反应中生成的羰基化合物的增加而增加，顺序为CH2O
• Maercker,A.; Theysohn,W., Justus Liebigs Annalen der Chemie, 1972, vol. 759, p. 132 - 157
  作者：Maercker,A.、Theysohn,W.

  DOI：——

  日期：——
• Access to functionalized cyclopropylcarbinyl compounds from homoallylic ethers via zirconocene intermediates
  作者：Jean-Luc Vasse、Jan Szymoniak

  DOI：10.1016/j.tetlet.2004.06.122

  日期：2004.8

  Cyclopropylcarbinylzirconium complexes were generated from homoallylic ethers and zirconocene (CP2ZrCl2/2n-BuLi). They underwent further in situ transformations that is, bromination-substitution, transmetallation-functionalization and insertion reactions to afford various cyclopropylcarbinyl derivatives. In contrast, ring-opening products could be selectively obtained by treating the zirconium complex with MeLi, prior to functionalization. (C) 2004 Elsevier Ltd. All rights reserved.
• Reaction of 1,1-diphenyl-2-vinylcyclopropane with tetracyanoethylene, diene, diborane, and dibromocarbene. Formation of unusual adducts after rearrangements supporting a two-step process
  作者：Nobujiro Shimizu、Takashi Fujioka、Shinichi Ishizuka、Takashi Tsuji、Shinya Nishida

  DOI：10.1021/ja00460a022

  日期：1977.8
• Structure-activity studies on benzhydrol-containing nipecotic acid and guvacine derivatives as potent, orally-active inhibitors of GABA uptake
  作者：Michael R. Pavia、Sandra J. Lobbestael、David Nugiel、Daniel R. Mayhugh、Vlad E. Gregor、Charles P. Taylor、Roy D. Schwarz、Laura Brahce、Mark G. Vartanian

  DOI：10.1021/jm00100a032

  日期：1992.10

  The introduction of lipophilic groups onto the ring nitrogen of nipecotic acid and guvacine, two known GABA uptake inhibitors, afforded potent, orally-active anticonvulsant drugs. A series of compounds is reported which explores the structure-activity relationships (SAR) in this series. Among the areas explored: side-chain SAR (aromatic-, heterocyclic-, and tricyclic-containing side chains) and modifications to the tetrahydropyridine ring. The benzhydrol ether-containing side chains afforded the most potent compounds with several exhibiting in vitro IC50 values for GABA uptake of <1 muM (including 5, Table 1; 37, 43, Table IV; and 44, Table V). Compound 44 was selected for extensive evaluation and subsequently progressed to Phase 1 clinical trials with severe adverse effects seen after single dose administration to humans.