3-(4-tert-butylphenyl)cyclohex-2-enone

• 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: 3-(4-tert-butylphenyl)cyclohex-2-enone
• 英文别名: 4'-(tert-butyl)-5,6-dihydro-[1,1'-bi(phenyl)]-3(4H)-one；3-(4-Tert-butylphenyl)cyclohex-2-en-1-one
• 化学式: C₁₆H₂₀O
• 分子量: 228.334
• InChiKey: NHMRJTYUXZSIBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  3-(4-tert-butylphenyl)cyclohex-2-enone 在 氨 、 lithium 、 叔丁醇 作用下， 以 乙醚 为溶剂， 反应 0.17h， 以99%的产率得到3-(4-tert-butylphenyl)cyclohexan-1-one
  参考文献：
  名称：

  Synthesis and pharmacology of 1-deoxy analogs of CP-47,497 and CP-55,940

  摘要：

  A series of 1-deoxy analogs of CP-47,497 (8 and 13, n = 0-7) and 1-deoxy analogs of CP-55,940 (9, n = 0-7) have been synthesized and their affinities for the cannabinoid CB1 and CB2 receptors have been determined. Although the majority of these compounds exhibit selectivity for the CB2 receptor, none have greater than modest affinity for either receptor. The interactions of these 1-deoxy nontraditional cannabinoids with the CB2 receptor are discussed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.09.033
• 作为产物：
  描述：

  1-(p-t-butylphenyl)cyclohexene 在 eosin 作用下， 以 乙腈 为溶剂， 反应 0.67h， 以78%的产率得到3-(4-tert-butylphenyl)cyclohex-2-enone
  参考文献：
  名称：

  Visible Light Promoted Allylic C–H Oxidation

  摘要：

  A mild and efficient one-pot visible light-induced method has been developed for the allylic oxidation. The oxidation of allylic systems has played a prominent role in this context as possibly the most widely applied C-H functionalization, owing to the utility of enones. The allylic C-H oxidation is relatively simple and predictable, even on a preparative scale, because active species generated at the allylic position are stabilized by the double bond.

  DOI：

  10.5562/cca3126

文献信息

• Selective arylation at the vinylic site of cyclic olefins
  作者：Xiaojin Wu、Jianrong (Steve) Zhou

  DOI：10.1039/c3cc41722k

  日期：——

  Cyclic olefins usually give Heck products having an aryl ring residing at the allylic or homoallylic position. We describe herein a new method that allows arylation at the vinylic position of various cyclic olefins.

  环烯烃通常得到具有在烯丙基或均烯丙基位置上的芳基环的Heck产物。我们在本文中描述了一种新的方法，该方法允许在各种环状烯烃的乙烯基位置进行芳基化。
• Continuous-Flow Synthesis of <i>meta</i>-Substituted Phenol Derivatives
  作者：Jeong Hyeon Park、Chan Yi Park、Mi Jin Kim、Min Uk Kim、Young Joon Kim、Geon-Hee Kim、Chan Pil Park

  DOI：10.1021/acs.oprd.5b00077

  日期：2015.7.17

  complementary microreactor technologies were developed for the study of biphasic gas–liquid reactions and preparation of meta-substituted phenol derivatives. The first capillary microreactor, composed of a T-junction and simple capillary, enabled oxidative Heck/dehydrogenation on a microgram scale with a shortened reaction time; the total sequence time for oxidative Heck/dehydrogenation reactions was optimized

  开发了两种互补的微反应器技术，用于研究气液两相反应和间位反应的制备取代的苯酚衍生物。第一个毛细管微反应器由T型接头和简单的毛细管组成，可实现微克级的氧化Heck /脱氢反应，并缩短了反应时间。氧化性Heck /脱氢反应的总顺序时间从传统的批处理系统中的2160分钟优化到微化学系统中的130分钟。第二个管内微反应器由可透气的内管和不可透气的外管组成，在由第一个微克规模的研究确定的最佳安全性和经济性条件下，成功地进行了克级合成。这两种微反应器在探索涉及气态和液态试剂的反应方面具有巨大潜力。
• Aerobic Oxidative Heck/Dehydrogenation Reactions of Cyclohexenones: Efficient Access to<i>meta</i>-Substituted Phenols
  作者：Yusuke Izawa、Changwu Zheng、Shannon S. Stahl

  DOI：10.1002/anie.201209457

  日期：2013.3.25

  catalyst, employing a 6,6′‐dimethyl‐2,2′‐bipyridine ligand, promotes both the aerobic oxidative Heck coupling and dehydrogenation reactions of cyclohexenones. These reactions may be combined in a one‐pot sequence to enable the straightforward synthesis of meta‐substituted phenols (see scheme).

  争夺（间）位：一种新型双阳离子钯（II）催化剂，采用 6,6'-二甲基-2,2'-联吡啶配体，促进环己烯酮的有氧氧化 Heck 偶联和脱氢反应。这些反应可以以一锅法顺序组合，以实现间位取代酚的直接合成（参见方案）。
• Copper/Selectfluor-System-Catalyzed Dehydration-Oxidation of Tertiary Cyclo­alcohols: Access to β-Substituted Cyclohex-2-enones, 4-Arylcoumarins, and Bi­aryls
  作者：Shaobo Ren、Jian Zhang、Jiahui Zhang、Heng Wang、Wei Zhang、Yunkui Liu、Miaochang Liu

  DOI：10.1002/ejoc.201500610

  日期：2015.8

  A route to β-substituted cyclohex-2-enones, 4-arylcoumarins, and biaryls has been developed. This approach involves a one-pot Cu0/Selectfluor-catalyzed dehydration–oxidation of tertiary cycloalcohols. Thus, by using 2 equiv. of Selectfluor at 25 °C, the dehydration–oxidation of tertiary cyclohexanols and oxabenzocyclohexanols gave β-substituted cyclohex-2-enones and 4-arylcoumarins, respectively; whereas

  β-取代的环己-2-烯酮、4-芳基香豆素和联芳基的路线已经开发出来。这种方法涉及一锅 CuO/Selectfluor 催化的叔环醇脱水氧化。因此，通过使用 2 equiv。Selectfluor 在 25 °C 下，叔环己醇和氧杂苯并环己醇的脱水-氧化分别得到 β-取代的环己-2-烯酮和 4-芳基香豆素；而叔环己醇的脱水-氧化使用 2.5 当量得到联芳基化合物作为最终产物。Selectfluor 在 80 °C。
• Highly Enantioselective Synthesis of Chiral Cyclic Allylic Amines via Rh-Catalyzed Asymmetric Hydrogenation
  作者：Ming Zhou、Tang-Lin Liu、Min Cao、Zejian Xue、Hui Lv、Xumu Zhang

  DOI：10.1021/ol501421g

  日期：2014.7.3

  enantioselective asymmetric hydrogenation of cyclic dienamides catalyzed by an Rh-DuanPhos complex has been developed, which provides a readily accessible method for the synthesis of chiral cyclic allylic amines in excellent enantioselectivities (up to 99% ee). The products are valuable chiral building blocks and could be easily transformed to multisubstituted cyclohexane derivatives.

  已经开发了由Rh-DuanPhos配合物催化的环状二烯酰胺的高度区域选择性和对映选择性不对称氢化反应，它为合成手性环状烯丙基胺具有出色的对映选择性（高达99％ee）提供了一种容易获得的方法。该产品是有价值的手性结构单元，可以轻松转化为多取代的环己烷衍生物。