2-hydroxy-4,4-diphenylcyclohexa-2,5-dien-1-one | 73982-27-1

• 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-hydroxy-4,4-diphenylcyclohexa-2,5-dien-1-one
• 英文别名: 2-Hydroxy-4,4-diphenylcyclohexa-2,5-dien-1-on
• CAS: 73982-27-1
• 化学式: C₁₈H₁₄O₂
• 分子量: 262.308
• InChiKey: BAKBZONMQBWOPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-hydroxy-4,4-diphenylcyclohexa-2,5-dien-1-one 在 盐酸 作用下， 以 乙醚 为溶剂， 反应 16.0h， 以90%的产率得到4,5-diphenylcatechol
  参考文献：
  名称：

  Electronic and Steric Effects in the Dienone-Phenol Rearrangement of 2-Hydroxy- and 2-Alkoxycyclohexa-2,5-dien-1-ones

  摘要：

  A series of 4,4,6-trisubstituted-2-hydroxy- and -2-alkoxycyclohexa-2,5-dien-1-ones (7 and 8) were prepared, where the substituent at C-6 was H, CH3, Ph, tert-butyl, or Oft. In the acid-catalyzed dienone-phenol rearrangement of 7 and 8, the C-4 substituent migrates regioselectively to C-5, completely shunning the enol double bond, even though the substituents at C-6 are substantially larger than the OH or OMe groups situated at C-2. The C-5 regioselectivity in hydroxy dienones 7a-f and 8a,b, as well as the decreased rate of reaction in the case of dienone 7g, can be simply rationalized by considering the relative electron density at C-3 vs C-5 in the protonated form of ? or 8. Our results clearly indicate that the regioselectivity of the dienone-phenol rearrangement in these enolic systems is completely controlled by the electronic factors, which far outweigh any steric considerations.

  DOI：

  10.1021/jo00086a038
• 作为产物：
  描述：

  4,4-二苯基-2-环己烯-1-酮 在 18-冠醚-6 KO₂ 作用下， 以 苯 为溶剂， 反应 16.0h， 以80%的产率得到2-hydroxy-4,4-diphenylcyclohexa-2,5-dien-1-one
  参考文献：
  名称：

  烯醇与超氧阴离子自由基的反应[0 2 ??? ] 1。2,3-不饱和-δ-戊内酯的合成。

  摘要：

  3-和4-羟基香豆素（和）以及2-羟基-2,5-环己二烯-1-酮-用KO反应2 / 18-冠-6苯。烯醇氢的初始去质子化之后是O 2 / t-（对于和）的亲核攻击和/或所得阴离子的自氧化（对于和- ）。还描述了由相应的2-环己烯-1-酮方便地合成2，3-不饱和-δ-戊内酯。

  DOI：

  10.1016/s0040-4039(00)87089-6

文献信息

• Preparation of oxacycloalkenones
  申请人：——

  公开号：US04376733A1

  公开（公告）日：1983-03-15

  Oxacycloalkenones are prepared by reacting a cycloalkenone with a base in the presence of a dioxygen source in a suitable solvent and isolating the desired product. 1-Hydroxy 2-oxa-3-oxo-.DELTA..sup.4 steroids are convenient synthetic precursors to 2-oxa-3-oxo-.DELTA..sup.4 steroids which find use in modern clinical therapy.

  Oxacycloalkenones是通过在适当的溶剂中，将环氧烯酮与碱在二氧化碳源的存在下反应，并分离所需产物而制备的。1-羟基2-氧杂-3-酮-Δ4类固醇是方便的合成前体，可用于制备现代临床治疗中使用的2-氧杂-3-酮-Δ4类固醇。
• Superoxide anion radical (O2.bul.-)-mediated base-catalyzed autoxidation of enones
  作者：Aryeh A. Frimer、Pessia Gilinsky-Sharon、Gladis Aljadeff、Hugo E. Gottlieb、Judith Hameiri-Buch、Vered Marks、Rachel Philosof、Zilpa Rosental

  DOI：10.1021/jo00281a030

  日期：1989.9
• Superoxide anion radical (02.bul.-) mediated base-catalyzed autoxidation of .alpha.-keto enols
  作者：Aryeh A. Frimer、Pessia Gilinsky-Sharon、Gladis Aljadeff、Vered Marks、Zilpa Rosental

  DOI：10.1021/jo00281a031

  日期：1989.9
• The photosensitized oxidation of α-keto enols: A singlet oxygen approach to 2-oxasteroids
  作者：Aryeh A. Frimer、Shlomo Ripstos、Vered Marks、Gladis Aljadeff、Judith Hameiri-Buch、Pessia Gilinsky-Sharon

  DOI：10.1016/s0040-4020(01)96177-0

  日期：1991.9

  Fluoride ion catalyzed photosensitized singlet oxygenation of 2-hydroxycyclohexa-2,5-dien-1-ones 15a and b and the related steroidal alpha-keto enols 18a-g, generated the cyclohexenone lactols 16a-b and the corresponding steroidal analogs 19a-g generally in moderate to good yields (60-75%). Since the lactols can be conveniently reduced to the desired 2-oxasteroids in high yields, this 1O2 route presents itself as a synthetically acceptable alternative to the previously reported BCA approach3a for the preparation of 2-oxasteroids, especially in the case of base sensitive compounds.
• FRIMER, ARYEH A.;GILINSKY-SHARON, PESSIA;ALJADEFF, GLADIS;MARKS, VERED;RO+, J. ORG. CHEM., 54,(1989) N0, C. 4866-4872
  作者：FRIMER, ARYEH A.、GILINSKY-SHARON, PESSIA、ALJADEFF, GLADIS、MARKS, VERED、RO+

  DOI：——

  日期：——