2-hydroxy-5-methoxy-1-indanone | 7235-25-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-hydroxy-5-methoxy-1-indanone
• 英文别名: 2-hydroxy-5-methoxy-2,3-dihydro-1H-inden-1-one；2-hydroxy-5-methoxy-2,3-dihydroinden-1-one
• CAS: 7235-25-8
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: UCMMSLDOAHAVFZ-UHFFFAOYSA-N

物化性质

• 熔点：
  133-134 °C
• 沸点：
  370.5±42.0 °C(Predicted)
• 密度：
  1.310±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-hydroxy-5-methoxy-1-indanone 在 chromium(VI) oxide 、 氢气 作用下， 以 丙酮 为溶剂， 反应 0.17h， 以83%的产率得到5-methoxy-1,2-indandione
  参考文献：
  名称：

  使用HOF.CH（3）CN配合物的新型茚并酮的合成。

  摘要：

  DOI：

  10.1021/jo972088d
• 作为产物：
  描述：

  2-Acetoxy-5-methoxy-indan-1-on 在 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 生成 2-hydroxy-5-methoxy-1-indanone
  参考文献：
  名称：

  摘要：

  Crystal and molecular structures for aryl- and benzyl-substituted 3-hydroxy-3,4-dihydroisobenzopyran- 1-one are described. For the 4,4-dimethyl derivative, two monoclinic modifications are produced on sublimation: (1) P2(1)/c, a = 23: 668(6) Angstrom; b = 11.749(4) Angstrom; c = 7.215( 2) Angstrom; beta = 96.70(2) degrees; V = 1992: 6(10) Angstrom(3); (2) P2(1)/c, a = 11.509(4) Angstrom, b =12.429( 4) Angstrom, c = 6.933(2) Angstrom, beta = 91.12(3) degrees, V = 991.6( 6) Angstrom. In both, hydroxy groups are pseudoaxial, and molecules form dimeric complementary but noncooperative hydrogen bonds. In the 6-methoxy derivative (3), P2(1)/c; a = 14.185(7) Angstrom; b = 4.105( 4) Angstrom; c = 15.598(13) Angstrom; beta = 98.59(6) degrees; V = 898.1(10) Angstrom(3), the hydroxy group is pseudoequatorial, and the intermolecular hydrogen bonding forms infinite chains. In the 4,4-dimethyl-7-nitro derivative (4), C2/c, a = 19.365(4), b = 8.425(2), c = 13.464(4), beta = 92.62(2), V = 2194.2(7) Angstrom(3), the hydroxy group is pseudoaxial, and the intermolecular hydrogen bonding forms chains. Compared to the unmethylated compounds, the interbond angles within the ring at the dimethylated carbon are contracted.

  DOI：

  10.1023/a:1024226029750

文献信息

• A Unified Approach for Divergent Synthesis of Heterocycles <i>via</i> TMSOTf‐Catalyzed Formal [3+2] Cycloaddition of Electron‐Rich Alkynes
  作者：Ping Chen、Wei Cao、Xiangqian Li、Dayong Shi

  DOI：10.1002/adsc.202100769

  日期：2021.10.19

  construction of polysubstituted five-membered heterocycles via TMSOTf-catalyzed formal [3+2] cycloaddition of electron-rich alkynes, which features free from any metal, atom economy and water as the main by-product. Furthermore, alkenyl ether adduct has been verified as the key intermediate. Notably, by utilizing this approach, we can synthesize a broad range of polysubstituted furans, thiophenes and pyrroles

  我们提出了一种通过TMSOTf 催化的富电子炔烃的正式 [3+2] 环加成来构建多取代五元杂环的合成方案，其特点是不含任何​​金属、原子经济性和水作为主要副产品。此外，烯基醚加合物已被证实为关键中间体。值得注意的是，通过利用这种方法，我们可以合成范围广泛的多取代呋喃、噻吩和吡咯，并将这种转化扩展到提供稠合聚杂环。该反应可以在克规模上实现，相应的产品是用于生产多种潜在有用支架的中间体。
• Enantioselective synthesis of indanone spiro-isochromanone derivatives <i>via</i> a dinuclear zinc-catalyzed Michael/transesterification tandem reaction
  作者：Xiao-Chao Yang、Meng Xu、Jin-Bao Wang、Meng-Meng Liu、François Mathey、Yuan-Zhao Hua、Min-Can Wang

  DOI：10.1039/d0ob00541j

  日期：——

  An enantioselective Michael/transesterification tandem reaction of α-hydroxy indanones with ortho-ester chalcones was realized using dinuclear zinc catalysts. A series of enantiomerically pure spiro[indanone-2,3'-isochromane-1-one] derivatives were obtained in good yields with excellent stereoselectivities (up to >20 : 1 dr, up to >99% ee). This protocol could be conducted on a gram scale without affecting

  使用双核锌催化剂实现了α-羟基茚满酮与原酸酯查耳酮的对映选择性迈克尔/酯交换串联反应。以良好的收率和优异的立体选择性（高达> 20：1 dr，高达> 99％ee）获得了一系列对映体纯的螺[茚满酮-2,3'-异色烷-1-酮]衍生物。该协议可以以克为单位进行，而不会影响其立体选择性。另外，通过3ac的X射线晶体学分析确定产物的绝对立体化学，并且观察到正非线性效应。最后，提出了一个可能的催化循环来解释对映选择性的起源。
• Synthesis of Chiral Bispirotetrahydrofuran Oxindoles by Cooperative Bimetallic-Catalyzed Asymmetric Cascade Reaction
  作者：Meng-Meng Liu、Xiao-Chao Yang、Yuan-Zhao Hua、Jun-Biao Chang、Min-Can Wang

  DOI：10.1021/acs.orglett.9b00386

  日期：2019.4.5

  Under mild conditions, a broad range of bispirotetrahydrofuran oxindoles have been synthesized with excellent stereoselectivities through the cascade Michael/hemiketalization/Friedel–Crafts reaction of β,γ-unsaturated α-ketoamide and 2-hydroxy-1-indanone. The reaction can be performed on a gram scale with low catalyst loading (2 mol %) without impacting its efficiency.

  通过协同双核锌-AzePhenol催化剂描述了一种对映选择性构建双螺四氢呋喃羟吲哚的新的有效途径。在温和的条件下，通过β，γ-不饱和α-酮酰胺和2-羟基-1-茚满酮的级联迈克尔/半缩酮化/弗里德-克拉夫茨反应，合成了多种具有优良立体选择性的双螺四氢呋喃恶吲哚。该反应可以以克级进行，催化剂负载量低（2mol％），而不会影响其效率。
• Dinuclear Zinc-Catalyzed Asymmetric Tandem Reaction of α-Hydroxy-1-indanone: Access to Spiro[1-indanone-5,2′-γ-butyrolactones]
  作者：Meng-Meng Liu、Xiao-Chao Yang、Yuan-Zhao Hua、Jun-Biao Chang、Min-Can Wang

  DOI：10.1021/acs.orglett.9b02658

  日期：2019.9.6

  A highly efficient method for the enantioselective build of spiro[1-indanone-5,2'-γ-butyrolactones] has been developed through the tandem Michael/transesterification reaction of α-hydroxy-1-indanone and α,β-unsaturated esters. A broad range of spiro(1-indanone-butyrolacones) with contiguous stereocenters have been synthesized with excellent stereoselectivities (up to >20:1 dr, up to >99% ee) under

  通过α-羟基-1-茚满酮与α，β-不饱和酯的串联迈克尔/酯交换反应，开发了一种高效的螺环[1-茚满酮-5,2'-γ-丁内酯]对映选择性构建方法。在双核锌络合物的催化下，已合成出具有连续立体中心的多种螺（1-茚满酮-丁酮），具有出色的立体选择性（高达> 20：1 dr，高达> 99％ee）。而且，该反应可以以克规模进行，而不会影响其立体选择性。提出了一种可能的机制。
• Stabilization of <i>sp</i>‐Hybridized Nitrogen Cation by Lewis Acid‐Base Complex Formation with Intramolecular Iodine
  作者：Tomohiro Fujino、Tadashi Hyodo、Yuko Otani、Kentaro Yamaguchi、Tomohiko Ohwada

  DOI：10.1002/chem.202303393

  日期：2024.1.22

  Anchimeric interaction with an sp-hybridized nitrogen cation with iodine affords an isolable acid-base complex. The N−I bonding is non-covalent but rather strong, while the O−I bond of the ligand is ionic and weak, facilitating ligand exchange in the presence of a Brønsted acid. The generated I+ cation species can be employed for α-hydroxylation of ketones.

  sp-杂化氮阳离子与碘的嵌合相互作用提供了可分离的酸碱复合物。 N−I 键是非共价键，但相当强，而配体的 O−I 键是离子键且弱，在布朗斯台德酸存在下促进配体交换。生成的 I +阳离子可用于酮的 α-羟基化。