3-羟基-5-苯基-2-环己烯-1-酮 | 35376-44-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-羟基-5-苯基-2-环己烯-1-酮
• 英文名称: 5-Phenyl-dihydroresorcin
• 英文别名: 3-Hydroxy-5-phenyl-cyclohex-2-enone；3-hydroxy-5-phenylcyclohex-2-en-1-one
• CAS: 35376-44-4
• 化学式: C₁₂H₁₂O₂
• mdl: MFCD00463813
• 分子量: 188.226
• InChiKey: ZFVDSCASCRHXCP-UHFFFAOYSA-N

物化性质

• 熔点：
  186-187℃
• 沸点：
  329.9±42.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2914400090

反应信息

• 作为反应物：
  描述：

  3-羟基-5-苯基-2-环己烯-1-酮 在 palladium on activated charcoal 二苯醚 作用下， 生成 5-phenylresorcinol
  参考文献：
  名称：

  Chandrasekharan,V. et al., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1978, vol. 16, p. 970 - 972

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲醛 在 sodium methylate 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 8.0h， 生成 3-羟基-5-苯基-2-环己烯-1-酮
  参考文献：
  名称：

  Identification of substituted 3-hydroxy-2-mercaptocyclohex-2-enones as potent inhibitors of human lactate dehydrogenase

  摘要：

  A novel class of 3-hydroxy-2-mercaptocyclohex-2-enone-containing inhibitors of human lactate dehydrogenase (LDH) was identified through a high-throughput screening approach. Biochemical and surface plasmon resonance experiments performed with a screening hit (LDHA IC50 = 1.7 mu M) indicated that the compound specifically associated with human LDHA in a manner that required simultaneous binding of the NADH co-factor. Structural variation of this screening hit resulted in significant improvements in LDHA biochemical inhibition activity (best IC50 = 0.18 mu M). Two crystal structures of optimized compounds bound to human LDHA were obtained and explained many of the observed structure-activity relationships. In addition, an optimized inhibitor exhibited good pharmacokinetic properties after oral administration to rats (F = 45%). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.06.076

文献信息

• Cyclization of Cyanoethylated Ketones as a Route to 6-Substituted Indole Derivatives
  作者：Jan Bergman、Birgitta Stensland

  DOI：10.1002/jhet.2048

  日期：2014.1

  δ‐Cyanoketones are quickly cyclized with KOtBu to 3‐aminocyclohex‐2‐enone derivatives, which in turn will give substituted indoles when treated with oxalyl chloride. Thus, 3‐amino‐6,6‐dimethylcyclohex‐2‐enone gave 3‐chloro‐6,6‐dimethyl‐2,5,6,7‐tetrahydroindole‐2,5‐dione, whose structure was corroborated by X‐ray crystallography, whereas the corresponding molecule without the blocking gem‐dimethyl groups

  δ-氰基酮可通过KOtBu快速环化成3-氨基环己-2-烯酮衍生物，当用草酰氯处理时，它们会生成取代的吲哚。因此，3-氨基-6,6-二甲基环己-2-烯酮产生了3-氯-6,6-二甲基-2,5,6,7-四氢吲哚-2,5-二酮，其结构得到了X射线的证实。晶体学，而没有封闭的二甲基-二甲基基团的相应分子3-氨基环己-2-烯酮通过氢转移得到6-氯-3-羟基羟吲哚。
• 2-Amino-quinazolin-5-ones
  申请人：Bellamacina R. Cornelia

  公开号：US20070027150A1

  公开（公告）日：2007-02-01

  2-Amino-quinazolin-5-one compounds, stereoisomers, tautomers, pharmaceutically acceptable salts, and prodrugs thereof; compositions that include a pharmaceutically acceptable carrier and one or more of the 2-amino-quinazolin-5-one compounds, either alone or in combination with at least one additional therapeutic agent. Methods of using the 2-amino-quinazolin-5-one compounds, either alone or in combination with at least one additional therapeutic agent, in the prophylaxis or treatment of cell proliferative diseases.

  2-氨基喹唑啉-5-酮化合物，立体异构体，互变异构体，药学上可接受的盐及其前药；包括药学上可接受的载体和一种或多种2-氨基喹唑啉-5-酮化合物的组合物，可以单独使用或与至少一种额外治疗剂结合使用。使用2-氨基喹唑啉-5-酮化合物的方法，可以单独使用或与至少一种额外治疗剂结合使用，用于预防或治疗细胞增殖性疾病。
• Formation of<i>meta</i>-Substituted Phenols by Transition Metal-Free Aromatization: Use of 2-Bromocyclohex-2-en-1-ones
  作者：Guojun Yu、Derrick L. J. Clive

  DOI：10.1021/acs.joc.6b01653

  日期：2016.9.16

  or other organometallic reagents to 2-halocyclohex-2-en-1-ones bearing an alkyl or aryl group at C-5, followed by mild acid treatment and exposure to 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) at room temperature, generates meta-substituted phenols in which the newly introduced meta substituent originates from the Grignard reagent. The range of effective organometallic reagents includes alkyl, allyl,

  将格利雅（Grignard）或其他有机金属试剂加到C-5上带有烷基或芳基的2-卤代环己-2-烯-1-酮中，然后进行弱酸处理并暴露于1,8-二氮杂双环[5.4.0]十一烷基-室温下的7-烯（DBU）生成间位取代的苯酚，其中新引入的间位取代基源自格氏试剂。有效的有机金属试剂的范围包括烷基，烯丙基，炔基，芳基和杂芳基化合物，包括具有氟取代基的那些。最初的卤代环己烯酮可以在C-6处质子化，并在添加格利雅（Grignard）之前与碳，氟或硫亲电试剂反应，从而生成高度取代的苯酚。
• A convenient, practical synthesis of substituted resorcinols: synthesis of DB-2073 and olivetol
  作者：Atul S. Kotnis

  DOI：10.1016/0040-4039(91)80801-c

  日期：1991.7

  A wide variety of easily accesible 1,3-cyclohexanediones are readily transformed to substituted dimethyl resorcinols with iodine and methanol.

  各种容易接近的1,3-环己二酮很容易被碘和甲醇转化为取代的二甲基间苯二酚。
• Environmentally benign, one-pot synthesis of pyrans by domino Knoevenagel/6π-electrocyclization in water and application to natural products
  作者：Ene Jin Jung、Byung Ho Park、Yong Rok Lee

  DOI：10.1039/c0gc00265h

  日期：——

  In water medium, environmentally benign, facile, and efficient synthesis of pyrans was achieved in good yields by the reactions of a variety of cyclic 1,3-dicarbonyls with several α,β-unsaturated aldehydes. The key strategy was a formal [3+3] cycloaddition by domino Knoevenagel/6π- electrocyclization. This methodology was applied to the synthesis of biologically interesting pyranocoumarin, pyranoquinolinone, and pyranonaphthoquinone derivatives along with selected natural and non-natural products.

  在水相介质中，通过多种环状1,3-二羰基化合物与若干α,β-不饱和醛的反应，以良好产率实现了吡喃的环保、简便、高效合成。关键策略是形式上的[3+3]环加成，通过多米诺Knoevenagel缩合/6π电环化反应实现。这一方法被应用于生物活性吡喃香豆素、吡喃喹啉酮和吡喃萘醌衍生物的合成，以及部分天然与合成产物的制备。