(R)-4-methyl-1-tetralone | 98213-39-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (R)-4-methyl-1-tetralone
• 英文别名: (R,S)-4-Methyl-3,4-dihydro-2H-naphthalen-1-one；(4R)-4-methyl-3,4-dihydro-2H-naphthalen-1-one
• CAS: 98213-39-9
• 化学式: C₁₁H₁₂O
• 分子量: 160.216
• InChiKey: SRLHDEROUKFEMJ-MRVPVSSYSA-N

物化性质

• 沸点：
  275.2±0.0 °C(Predicted)
• 密度：
  1.048±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  (R)-4-methyl-1-tetralone 在 lithium aluminium tetrahydride 、 copper diacetate 、 sodium 、 sodium hydride 、 锌 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 溶剂黄146 、 丙酮 、 mineral oil 为溶剂， 反应 5.0h， 生成 ethyl (2E,4E,6Z,8E)-8-[(4R)-4-methyl-3,4-dihydro-1(2H)-naphthalen-1-ylidene]-3,7-dimethyl-2,4,6-octatrienoate
  参考文献：
  名称：

  用于类视黄醇 X 受体的甲基取代的构象受限的雷克西汀激动剂显示出改善的癌症治疗和预防功效

  摘要：

  (2 E ,4 E ,6 Z ,8 Z )-8-(3',4'-Dihydro-1'(2 H )-naphthalen-1'-ylidene)-3,7-二甲基-2,3, 6-辛三烯酸，9cUAB30，是一种针对类视黄醇 X 核受体 (RXR) 的选择性 rexinoid。9cUAB30 显示出显着的化学预防能力，毒性很小，并正在作为一种新型癌症预防剂应用于临床。为了提高 9cUAB30 的效力，我们合成了 9cUAB30 的 4-甲基类似物，它在四氢萘酮环的 4-位引入了手性。报道了外消旋同系物和对映异构体的合成和生物学评价。我们证明了S- 对映异构体是最有效且毒性最小的，即使这些对映异构体在 RXR 的配体结合域中以相似的构象结合。

  DOI：

  10.1016/j.bmc.2013.11.039
• 作为产物：
  描述：

  trans-1-hydroxy-4-methyl-1,2,3,4-tetrahydronaphthalene 生成 (R)-4-methyl-1-tetralone
  参考文献：
  名称：

  KASAI, MASAJI;ZIFFER, HERMAN;SILVERTON, J. V., CAN. J. CHEM., 1985, 63, N 6, 1287-1291

  摘要：

  DOI：

文献信息

• UREA DERIVATIVES AND THEIR THERAPEUTIC USE IN THE TREATMENT OF, INTER ALIA, DISEASES OF THE RESPIRATORY TRACT
  申请人：Woo Chi-Kit

  公开号：US20130143914A1

  公开（公告）日：2013-06-06

  Compounds of formula (I) are p38 MAPK inhibitors, useful as anti-inflammatory agents in the treatment of, inter alia, diseases of the respiratory wherein R 1 is a radical of formula (IA) or (IB) or (IC): 10 Y is -0- or —S(0) p - wherein p is 0, 1 or 2; A is an optionally substituted cycloalkylene radical having 5, 6 or 7 ring atoms fused to a phenyl ring; and R 2 , R3b and R4b are as defined in the claims.

  式(I)的化合物是p38 MAPK抑制剂，在治疗呼吸系统疾病等炎症疾病中作为抗炎药物有用，其中R1是式(IA)或(IB)或(IC)的基团：Y是-0-或-S(0)p-，其中p为0、1或2；A是一个有5、6或7个环原子与苯环融合的可选择取代的环烷基基团；而R2、R3b和R4b如权利要求中所定义。
• Exploring the synthetic potential of a marine transaminase including discrimination at a remote stereocentre
  作者：Maria Schwarz、Edel J. Murphy、Aoife M. Foley、David F. Woods、Ignacio Abreu Castilla、F. Jerry Reen、Stuart G. Collins、Fergal O'Gara、Anita R. Maguire

  DOI：10.1039/d0ob01848a

  日期：——

  Transamination from 1-aminotetralins and 1-aminoindanes with differentiation of stereochemistry at both the site of reaction and at a remote stereocentre.

  1-氨基四氢萘和1-氨基茚烷的转氨基化反应，在反应位置和远程立体中心的立体化学差异。
• Tshiamala, Kabula; Kitane, Said; Vebrel, Joel, Bulletin des Societes Chimiques Belges, 1986, vol. 95, # 12, p. 1083 - 1098
  作者：Tshiamala, Kabula、Kitane, Said、Vebrel, Joel、Laude, Bernard

  DOI：——

  日期：——
• Efficient Kinetic Resolution in the Asymmetric Hydrosilylation of Imines of 3-Substituted Indanones and 4-Substituted Tetralones
  作者：Jaesook Yun、Stephen. L. Buchwald

  DOI：10.1021/jo991328h

  日期：2000.2.1

  Kinetic resolution of the N-methyl imines of 3-substituted indanones and 4-substituted tetralones could be accomplished by hydrosilylation with a chiral titanocene catalyst. N-Methyl imines of 4-substituted tetralones were resolved to yield, after hydrolysis of the unreacted starting materials, ketones with high ee's and the amine products with high diastereomeric and enantiomeric purity. The utility of this process was demonstrated in the synthesis of sertraline.
• Origin of Stereocontrol in Guanidine-Bisurea Bifunctional Organocatalyst That Promotes α-Hydroxylation of Tetralone-Derived β-Ketoesters: Asymmetric Synthesis of β- and γ-Substituted Tetralone Derivatives via Organocatalytic Oxidative Kinetic Resolution
  作者：Minami Odagi、Kota Furukori、Yoshiharu Yamamoto、Makoto Sato、Keisuke Iida、Masahiro Yamanaka、Kazuo Nagasawa

  DOI：10.1021/ja511149y

  日期：2015.2.11

  The mechanism of asymmetric a-hydroxylation of tetralone-derived beta-ketoesters with guanidine-bisurea bifunctional organocatalyst in the presence of cumene hydroperoxide (CHP) was examined by means of DFT calculations to understand the origin of the stereocontrol in the reaction. The identified transition-state model was utilized to design an enantioselective synthesis of beta- or gamma-substituted tetralones by catalytic oxidative kinetic resolution reaction of tetralone-derived beta-ketoesters. This kinetic resolution reaction proceeded with high selectivity, and selectivity factors (s value) of up to 99 were obtained. The potential utility of this oxidative kinetic resolution method for synthesis of natural products was confirmed by applying it to achieve an enantioselective synthesis of (+)-linoxepin (13) from beta-substituted tetralone rac-7 in only six steps.