3-methyl-1-naphthyl acetate | 76605-37-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-methyl-1-naphthyl acetate
• 英文别名: 1-acetoxy-3-methyl-naphthalene；(3-methylnaphthalen-1-yl) acetate
• CAS: 76605-37-3
• 化学式: C₁₃H₁₂O₂
• 分子量: 200.237
• InChiKey: KUVBMNMTMIJQGZ-UHFFFAOYSA-N

物化性质

• 沸点：
  323.4±11.0 °C(Predicted)
• 密度：
  1.128±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methyl-1-naphthyl acetate 在 甲醇 、 氢氧化钾 、 salcomine 、 氧气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 甲萘醌
  参考文献：
  名称：

  Construction of polycyclic systems by cyclocarbonylation. Part 3. A novel palladium- or platinum-catalyzed cyclocarbonylation reaction of cinnamyl compounds for synthesis of 1-naphthol derivatives

  摘要：

  DOI：

  10.1021/jo00251a031
• 作为产物：
  描述：

  一氧化碳 、 (2E)-2-methyl-3-phenylallyl acetate 在 bis-triphenylphosphine-palladium(II) chloride 、 乙酸酐 、 三乙胺 作用下， 以 苯 为溶剂， 160.0 ℃ 、6.08 MPa 条件下， 反应 4.0h， 以44%的产率得到3-methyl-1-naphthyl acetate
  参考文献：
  名称：

  Construction of polycyclic systems by cyclocarbonylation. Part 3. A novel palladium- or platinum-catalyzed cyclocarbonylation reaction of cinnamyl compounds for synthesis of 1-naphthol derivatives

  摘要：

  DOI：

  10.1021/jo00251a031

文献信息

• Aromatic carbon–hydrogen bond activation. Novel synthesis of 1-naphthol derivatives by palladium catalysed cyclocarbonylation of cinnamyl compounds
  作者：Yukio Koyasu、Hiroyuki Matsuzaka、Yoshitaka Hiroe、Yasuzo Uchida、Masanobu Hidai

  DOI：10.1039/c39870000575

  日期：——

  Palladium catalysed cyclocarbonylation of cinnamyl compounds gives 1-naphthol derivatives in good yields whereas the similar carbonylation of trans-β-bromostyrene yields a polymer containing benzindanone units.

  钯催化的肉桂基化合物的环羰基化以良好的收率得到了1-萘酚衍生物，而反式-β-溴苯乙烯的类似羰基化则得到了含有苯并丹酮单元的聚合物。
• Photochromic chromene compounds
  申请人：PPG Industries, Inc.

  公开号：US05200116A1

  公开（公告）日：1993-04-06

  Described are a series of novel photochromic benzopyran and naphthopyran compounds substituted with (1) a cyclopropyl group and (2) a phenyl, substituted phenyl, or 5-member aromatic heterocyclic group at the 2-position of the benzopyran or naphthopyran ring. Also described are organic host materials that contain or that are coated with such compounds. Articles such as ophthalmic or plano lenses that incorporate the novel pyran compounds or combinations of the novel pyran compounds with other complementary photochromic compounds are described.

  描述了一系列新颖的光致变色苯并吡喃和萘并吡喃化合物，其在苯并吡喃或萘并吡喃环的2-位置上取代有（1）环丙基基团和（2）苯基、取代苯基或5-成员芳香杂环基团。还描述了含有或被涂覆有这些化合物的有机宿主材料。描述了包含新型吡喃化合物或新型吡喃化合物与其他互补光致变色化合物组合的眼科或平面透镜等物品。
• A Total Synthesis of Yellowish Aphid Pigment Furanaphin through Fries Rearrangement Assisted by Boron Trifluoride-Acetic Acid Complex
  作者：Tetsuto Tsunoda、Taichi Nishimura、Takeki Iwata、Hironori Maegawa、Takeshi Nishii、Masami Matsugasako、Hiroto Kaku、Mitsuyo Horikawa、Makoto Inai

  DOI：10.1055/s-0031-1290429

  日期：2012.7

  The yellowish aphid pigment furanaphin, isolated from Aphis spiraecola and possessing cytotoxicity against HL-60 (human promyelocytic leukemia-60) cells, was synthesized by utilizing the Fries rearrangement assisted with a BF3·2AcOH complex as a key step. It was confirmed that the complex effectively mediated the reaction even though the compounds had an electron-withdrawing substituent.

  以BF3·2AcOH复合物辅助的Fries重排为关键步骤，从Aphis spiraecola中分离出对HL-60（human promyelocyticemia-60）细胞具有细胞毒性的黄色蚜虫色素呋喃酚。证实即使化合物具有吸电子取代基，该配合物也有效地介导了反应。
• Palladium- and platinum-catalyzed cyclocarbonylation reactions of substituted allyl acetates
  作者：Youichi Ishii、Masanobu Hidai

  DOI：10.1016/0022-328x(92)83237-c

  日期：1992.4

  The scope and limitation of novel palladium- and platinum-catalyzed cyclocarbonylation reactions of 3-arylallyl and 2,4-pentadienyl acetates are described. The detailed mechanism of these reactions is also discussed.
• KOYASU YUKIO; MATSUZAKA HIROYUKI; HIROE YOSHITAKA; UCHIDA YASUZO; HIDAI M+, J. CHEM. SOC. CHEM. COMMUN.,(1987) N 8, 575-576
  作者：KOYASU YUKIO、 MATSUZAKA HIROYUKI、 HIROE YOSHITAKA、 UCHIDA YASUZO、 HIDAI M+

  DOI：——

  日期：——