7-acetyl-1,1,2,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthalene | 86603-96-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 7-acetyl-1,1,2,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthalene
• 英文别名: 1-(3,5,5,7,8,8-hexamethyl-6,7-dihydronaphthalen-2-yl)ethanone
• CAS: 86603-96-5
• 化学式: C₁₈H₂₆O
• 分子量: 258.404
• InChiKey: WEZHTJYROPVQEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 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：

  7-acetyl-1,1,2,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthalene 在 盐酸羟胺 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 ethyl 5-(5,6,7,8-tetrahydro-3,5,5,7,8,8-hexamethyl-2-naphthalenyl)isoxazole-3-carboxylate
  参考文献：
  名称：

  Structure−Activity Relationship Studies of Novel Heteroretinoids:  Induction of Apoptosis in the HL-60 Cell Line by a Novel Isoxazole-Containing Heteroretinoid

  摘要：

  In a search for retinoic acid receptor (RAR and RXR)-selective ligands, a series of isoxazole retinoids was synthesized and evaluated in vitro in transcriptional activation and competition binding assays for RARs and RXRs. In addition, these compounds were evaluated for their differentiating, cytotoxic, and apoptotic activities. In general, these derivatives showed scarcely any binding affinity and were nest active in the transcriptional assay. However, among these isoxazole derivatives, the cis-isomer 14b was identified as a potent inducer of apoptosis, and its activity was found to be 6.5 and 4 times superior than that of 13-cis- and 9-cis-retinoic acids, respectively. On the other hand, compound 13b, which has the trans stereochemistry at the double bond, was found not to be active in the apoptotic assay, but it was endowed with appreciable differentiating activity. Therefore, it seems that the different stereochemistry of the double bond may be associated with a different biological activity: potent apoptotic activity for the cis-isomer but differentiating activity for the traits structure. This biological behavior was found, at least in part, for the 9-cis- and 13-cis-retinoic acids with respect to the all-trans-retinoic acid. Thus, structure 14b could offer an interesting model for the design of new compounds endowed with apoptotic activity.

  DOI：

  10.1021/jm991059n
• 作为产物：
  描述：

  1,1,2,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthalene 、 乙酰氯 在 三氯化铝 盐酸 作用下， 以 1,1-二氯乙烷 为溶剂， 生成 7-acetyl-1,1,2,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  Tetrahydronaphthalene derivatives and their production

  摘要：

  公式为：##STR1##其中R.sup.1和R.sup.2中的任意一个是氢、C.sub.1 -C.sub.4烷基或C.sub.1 -C.sub.4烷氧基，另一个是乙酰基，R.sup.3以拉式或光学活性形式为氢或甲基的四氢萘衍生物，这些衍生物可用作香水或香水生产中间体，从R.sup.4-苯和吡啶醛经过公式的中间化合物制备：##STR2##其中R.sup.4是氢、C.sub.1 -C.sub.4烷基或C.sub.1 -C.sub.4烷氧基，存在于6-和7-位置中的任一位置，A是氢、羧基、C.sub.2 -C.sub.5烷氧羰基、卤素、甲基、羟甲基或卤甲基。

  公开号：

  US04767882A1

文献信息

• Regioselective α-Deuteration of Michael Acceptors Mediated by Isopropylamine in D₂O/AcOD
  作者：Vinod G. Landge、Kendra K. Shrestha、Aaron J. Grant、Michael C. Young

  DOI：10.1021/acs.orglett.0c03839

  日期：2020.12.18

  hydrogen/deuterium exchange is an important method to access deuterated compounds for chemical and biological studies. Herein is reported the first method for the regioselective α-deuteration of enals and enones. The transformation features D2O and AcOD as deuterium sources and amines as organocatalysts. The deuteration strategy is scalable and works on enals with a variety of substituted arene or heterocycle

  特定地点的氢/氘交换是获取用于化学和生物研究的氘化化合物的重要方法。本文报道了第一种对 enals 和 enones 进行区域选择性 α-氘化的方法。转化的特点是 D 2 O 和 AcOD 作为氘源，胺作为有机催化剂。氘化策略是可扩展的，适用于具有各种取代芳烃或杂环基序以及烯酮的 enal。该方法已应用于氘代药物前体的合成。
• US4767882A
  申请人：——

  公开号：US4767882A

  公开（公告）日：1988-08-30
• US5362715A
  申请人：——

  公开号：US5362715A

  公开（公告）日：1994-11-08
• Structure−Activity Relationship Studies of Novel Heteroretinoids:  Induction of Apoptosis in the HL-60 Cell Line by a Novel Isoxazole-Containing Heteroretinoid
  作者：Daniele Simoni、Francesco Paolo Invidiata、Riccardo Rondanin、Stefania Grimaudo、Giuliana Cannizzo、Eleonora Barbusca、Ferdinando Porretto、Nicola D'Alessandro、Manlio Tolomeo

  DOI：10.1021/jm991059n

  日期：1999.12.2

  In a search for retinoic acid receptor (RAR and RXR)-selective ligands, a series of isoxazole retinoids was synthesized and evaluated in vitro in transcriptional activation and competition binding assays for RARs and RXRs. In addition, these compounds were evaluated for their differentiating, cytotoxic, and apoptotic activities. In general, these derivatives showed scarcely any binding affinity and were nest active in the transcriptional assay. However, among these isoxazole derivatives, the cis-isomer 14b was identified as a potent inducer of apoptosis, and its activity was found to be 6.5 and 4 times superior than that of 13-cis- and 9-cis-retinoic acids, respectively. On the other hand, compound 13b, which has the trans stereochemistry at the double bond, was found not to be active in the apoptotic assay, but it was endowed with appreciable differentiating activity. Therefore, it seems that the different stereochemistry of the double bond may be associated with a different biological activity: potent apoptotic activity for the cis-isomer but differentiating activity for the traits structure. This biological behavior was found, at least in part, for the 9-cis- and 13-cis-retinoic acids with respect to the all-trans-retinoic acid. Thus, structure 14b could offer an interesting model for the design of new compounds endowed with apoptotic activity.
• Tetrahydronaphthalene derivatives and their production
  申请人：Sumitomo Chemical Company, Limited

  公开号：US04767882A1

  公开（公告）日：1988-08-30

  Tetrahydronaphthalene derivatives of the formula: ##STR1## wherein either one of R.sup.1 and R.sup.2 is hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy and the other is acetyl and R.sup.3 is hydrogen or methyl in a racemic or optically active form, which are useful as perfumes or intermediates for production of perfumes, are prepared from an R.sup.4 -benzene and pyrocine through the intermediary compounds of the formula: ##STR2## wherein R.sup.4 is hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy present at either one of 6- and 7-positions and A is hydrogen, carboxyl, C.sub.2 -C.sub.5 alkoxycarbonyl, halogen, methyl, hydroxymethyl or halomethyl.

  公式为：##STR1##其中R.sup.1和R.sup.2中的任意一个是氢、C.sub.1 -C.sub.4烷基或C.sub.1 -C.sub.4烷氧基，另一个是乙酰基，R.sup.3以拉式或光学活性形式为氢或甲基的四氢萘衍生物，这些衍生物可用作香水或香水生产中间体，从R.sup.4-苯和吡啶醛经过公式的中间化合物制备：##STR2##其中R.sup.4是氢、C.sub.1 -C.sub.4烷基或C.sub.1 -C.sub.4烷氧基，存在于6-和7-位置中的任一位置，A是氢、羧基、C.sub.2 -C.sub.5烷氧羰基、卤素、甲基、羟甲基或卤甲基。