2,2-dibenzylcyclopentanone | 57772-75-5

• 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-dibenzylcyclopentanone
• 英文别名: 2,2-dibenzyl-cyclopentanone；2,2-Dibenzyl-cyclopentanon；2,2-Dibenzylcyclopentanon；2,2-Dibenzylcyclopentan-1-one
• CAS: 57772-75-5
• 化学式: C₁₉H₂₀O
• 分子量: 264.367
• InChiKey: BESPYDZFHBZGOW-UHFFFAOYSA-N

物化性质

• 熔点：
  39 °C
• 沸点：
  225 °C(Press: 16 Torr)
• 密度：
  1.100±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 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：

  2,2-dibenzylcyclopentanone 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 2,2-Dibenzylcyclopentyl xanthate
  参考文献：
  名称：

  Cyclization and rearrangement processes resulting from bromination of 3-benzylcycloalkenes

  摘要：

  DOI：

  10.1021/jo00062a043
• 作为产物：
  描述：

  2-bromo-3-phenyl-propene 在 tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate 、 三苯基膦氯金 、 叔丁基锂 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 、 正戊烷 为溶剂， 反应 7.17h， 生成 2,2-dibenzylcyclopentanone
  参考文献：
  名称：

  Dual Visible Light Photoredox and Gold-Catalyzed Arylative Ring Expansion

  摘要：

  A combination of visible light photocatalysis and gold catalysis is applied to a ring expansion-oxidative arylation reaction. The reaction provides an entry into functionalized cyclic ketones from the coupling reaction of alkenyl and allenyl cycloalkanols with aryl diazonium salts. A mechanism involving generation of an electrophilic gold(III)-aryl intermediate is proposed on the basis of mechanistic studies, including time-resolved FT-IR spectroscopy.

  DOI：

  10.1021/ja500716j

文献信息

• Reactivity of Lithium β-Ketocarboxylates: The Role of Lithium Salts
  作者：Mateo Berton、Rossella Mello、Paul G. Williard、María Elena González-Núñez

  DOI：10.1021/jacs.7b08450

  日期：2017.12.6

  Lithium β-ketocarboxylates 1(COOLi), prepared by the reaction of lithium enolates 2(Li+) with carbon dioxide, readily undergo decarboxylative disproportionation in THF solution unless in the presence of lithium salts, in which case they are indefinitely stable at room temperature in inert atmosphere. The availability of stable THF solutions of lithium β-ketocarboxylates 1(COOLi) in the absence of carbon

  β-酮基羧酸锂 1(COOLi)，由烯醇锂 2(Li+) 与二氧化碳反应制备，在 THF 溶液中很容易发生脱羧歧化反应，除非在锂盐存在的情况下，在这种情况下，它们在室温下无限稳定惰性气氛。在不存在二氧化碳的情况下，β-酮基羧酸锂 1(COOLi) 的稳定 THF 溶液的可用性允许与氮碱和烷基卤化物 3 发生反应，在酸性水解后得到 α-烷基酮 1(R)。因此，该序列代表使用二氧化碳作为可去除的导向基团，用于烯醇化锂 2(Li+) 的选择性单烷基化。
• ALKYLATION REACTION ACCOMPANIED BY DEALKOXYCARBONYLATION OF β-KETO ESTERS, GEMINAL DIESTERS AND α-CYANO ESTER IN HEXAMETHYLPHOSPHORIC TRIAMIDE (HMPA)
  作者：Morio Asaoka、Kazutoshi Miyake、Hisashi Takei

  DOI：10.1246/cl.1975.1149

  日期：1975.11.5

  In the presence of alkali halide β-keto esters, geminal diesters and ethyl cyanoacetate in HMPA reacted with alkyl halides to give α-alkylated ketones, esters and nitrile, respectively. α-Acetyl-γ-butyrolactone and its derivative afforded corresponding acylcyclopropane derivatives.

  在碱金属卤化物β-酮酯存在下，HMPA 中的孪生二酯和氰基乙酸乙酯与烷基卤化物反应，分别生成α-烷基化酮、酯和腈。α-乙酰基-γ-丁内酯及其衍生物得到相应的酰基环丙烷衍生物。
• Visible Light Photoredox-Catalyzed Arylative Ring Expansion of 1-(1-Arylvinyl)cyclobutanol Derivatives
  作者：Su Jin Kwon、Dae Young Kim

  DOI：10.1021/acs.orglett.6b02201

  日期：2016.9.16

  A visible light mediated photocatalytic arylation/ring expansion of alkenylcyclobutanols has been developed. This approach provides a mild and operationally simple access to the synthesis of functionalized cyclic ketones from the coupling reaction of alkenylcyclobutanols with aryldiazonium salts.

  已经开发了可见光介导的烯基环丁醇的光催化芳基化/扩环。该方法为从烯基环丁醇与芳基重氮盐的偶合反应合成官能化环酮提供了温和且操作简单的途径。
• Highly Enantioselective Oxazaborolidine-Catalyzed Reduction of 1,3-Dicarbonyl Compounds: Role of the Additive Diethylaniline
  作者：Rong-Jie Chein、Ying-Yeung Yeung、E. J. Corey

  DOI：10.1021/ol900258f

  日期：2009.4.2

  The oxazaborolidine-catalyzed reduction of 2,2-disubstituted cycloalkan-1,3-diones or hindered 2,2-disubstituted cyclic ketones using catecholborane as reductant proceeds with greater enantioselectivity when N,N-diethylaniline is added. It has now been shown that the effect of this additive is to catalyze the conversion of a harmful minor impurity in catalyst preparations to the active catalyst.
• New cyclopentane derivatives as inhibitors of steroid metabolizing enzymes AKR1C1 and AKR1C3
  作者：Bogdan Štefane、Petra Brožič、Matej Vehovc、Tea Lanišnik Rižner、Stanislav Gobec

  DOI：10.1016/j.ejmech.2009.01.028

  日期：2009.6

  A series of cyclopentane derivatives was synthesized and evaluated for inhibition of the steroid metabolizing enzymes AKR1C1 and AKR1C3. Selective inhibitors that are active in the low micromolar range were identified. These compounds represent promising starting points in the development of new anticancer agents for the treatment of hormone-dependent forms of cancer and other diseases where AKR1C1 and AKR1C3 are involved. (C) 2009 Elsevier Masson SAS. All rights reserved.