1-Ethinyl-1-hydroxy-indan | 20470-48-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 1-Ethinyl-1-hydroxy-indan
• 英文别名: 1-Ethynyl-1-indanol；1-ethynyl-indan-1-ol；1-Aethinyl-indan-1-ol；1-Ethynyl-2,3-dihydro-1H-inden-1-ol；1-ethynyl-2,3-dihydroinden-1-ol
• CAS: 20470-48-8
• 化学式: C₁₁H₁₀O
• 分子量: 158.2
• InChiKey: XRPSBLRPYIACBC-UHFFFAOYSA-N

物化性质

• 熔点：
  72-74 °C(Solv: ligroine (8032-32-4))
• 沸点：
  263.9±19.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-Ethinyl-1-hydroxy-indan 在 硫酸 、 sodium hydride 、 mercury(II) oxide 作用下， 以 四氢呋喃 为溶剂， 生成 Methyl 4'-oxospiro[1,2-dihydroindene-3,5'-furan]-2'-carboxylate
  参考文献：
  名称：

  Analogues of Acifran:  Agonists of the High and Low Affinity Niacin Receptors, GPR109a and GPR109b

  摘要：

  Recently identified GPCRs, GPR109a and GPR109b, the high and low affinity receptors for niacin, may represent good targets for the development of HDL elevating drugs for the treatment of atherosclerosis. Acifran, an agonist of both receptors, has been tested in human subjects, yet until recently very few analogs had been reported. We describe a series of acifran analogs prepared using newly developed synthetic pathways and evaluated as agonists for GPR109a and GPR109b, resulting in identification of compounds with improved activity at these receptors.

  DOI：

  10.1021/jm070022x
• 作为产物：
  描述：

  1-茚酮 在 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.08h， 生成 1-Ethinyl-1-hydroxy-indan
  参考文献：
  名称：

  通过对苯二酚的邻-NQM的半松果醇重排构建部分保护的不对称联芳基二醇

  摘要：

  已经实现了由AgBF 4催化的部分保护的不对称联芳基二醇的构建。该方法通过邻-NQM生成/ semipinacol重排级联促进了两个新的芳基环的形成和两个羟基的引入（一个游离基和一个TBS保护基），具有高原子经济性和阶梯经济性，可提供多种阵列温和条件下制备部分保护的不对称联芳基二醇。

  DOI：

  10.1021/acs.orglett.0c03717

文献信息

• Mild conversion of propargylic alcohols to α,β-unsaturated enones in ionic liquids (ILs); a new ‘metal free’ life for the Rupe rearrangement
  作者：Ganesh C. Nandi、Benjamin M. Rathman、Kenneth K. Laali

  DOI：10.1016/j.tetlet.2013.09.028

  日期：2013.11

  free protocol for the conversion of propargylic alcohols to cyclic and acyclic α,β-unsaturated enones via the Rupe rearrangement is reported. The method utilizes the Brønsted acidic ionic liquid [BMIM-SO3H][OTf] as catalyst and [BMIM][PF6] as solvent and offers the potential for recycling and reuse of the IL solvent. The feasibility to synthesize bicyclic fused cyclopentenone derivatives via a Rupe → Aldol → Nazarov

  报道了通过Rupe重排将炔丙醇转化为环状和无环α，β-不饱和烯酮的温和且无选择性的过渡金属方案。该方法利用布朗斯台德酸性离子液体[BMIM-SO 3 H] [OTf]作为催化剂，[BMIM] [PF 6 ]作为溶剂，为IL溶剂的再循环和再利用提供了潜力。还证明了利用该方案经由Rupe→Aldol→Nazarov序列合成双环稠合的环戊烯酮衍生物的可行性。
• Gold/Brønsted Acid Relay Catalysis for Enantioselective Construction of Spirocyclic Diketones
  作者：Deyun Qian、Junliang Zhang

  DOI：10.1002/chem.201301208

  日期：2013.5.27

  opportunities: A redox‐, atom‐, and step‐economical asymmetric cascade reaction for the synthesis of chiral spirocyclic architectures with two contiguous stereocenters in high yields and excellent enantioselectivities by using a gold/chiral Brønsted acid relay catalysis system is described (see scheme). The results suggest that the chiral Brønsted acid rather than the chiral gold phosphate complex serves as

  千载难逢的机会：描述了使用金/手性布朗斯台德酸中继催化系统，以高产率和优异对映选择性合成具有两个连续立体中心的手性螺环结构的氧化还原，原子和阶梯经济的不对称级联反应（参见方案） ）。结果表明，手性布朗斯台德酸而不是手性磷酸金配合物是对映体确定步骤的真正催化剂。
• Enantioselective carboxylative cyclization of propargylic alcohol with carbon dioxide under mild conditions
  作者：Shiliang Xie、Xiaotong Gao、Feng Zhou、Haihong Wu、Jian Zhou

  DOI：10.1016/j.cclet.2019.05.060

  日期：2020.2

  Abstract An enantioselective carboxylative cyclization of propargylic alcohols and CO2 was realized under mild conditions, based on a kinetic resolution strategy, which enabled the synthesis of chiral cyclic carbonates and propargylic alcohols with promising yield and enantioselectivity simultaneously.

  摘要在动力学拆分策略的基础上，在温和条件下实现了炔丙醇和CO2的对映选择性羧化环化反应，使合成手性环状碳酸酯和炔丙醇具有良好的收率和对映选择性。
• Derivatives of 4,5-dihydro-4-oxofuran-2-carboxylic acid, especially for use as hypolipidemic agents, processes for their preparation, pharmaceutical compositions comprising them, tetrahydropyran-2,3,5-triones useful in the preparation of the said derivatives and a process for preparing these tetrahydropyran-2,3,5-triones
  申请人：AMERICAN HOME PRODUCTS CORPORATION

  公开号：EP0006305A1

  公开（公告）日：1980-01-09

  Compounds of formula I in which R1 and R2 each is lower alkyl, cyclo(lower)alkyl, lower alkoxy(lower)alkylene, phenyl or phenyl mono- or disubstituted with lower alkyl, lower alkoxy, halo, nitro or trifluoromethyl; or RI and R2 together form a -(CH2)m-X-(CH2)n- chain wherein m and n each is an integer from one to four and X is methylene, oxa or thia; or R1 and R2 together with the carbon atom to which they are joined form a spiro-[1,2,3,4-tetrahydronaphthalene]-1 or spiro[indan]-1 radical; R3 is hydrogen or lower alkyl; and R' is hydrogen, lower alkyl, cyclo(lower)alkyl, phenyl(lower)alkylene, amino-(lower)alkylene, lower alkylamino(lower)alkylene, di(lower alkyl)amino(lower)alkylene or 3-pyridinyl(lower)alkylene, or a therapeutically acceptable addition salt thereof are disclosed which possess hypolipidemic activity, and can be used in pharmaceutical compositions. The compounds of formula I may be prepared by cyclising a corresponding compound of formula X and if desired esterifying. Tetrahydropyran-2,3,5-trione intermediates are also disclosed.

  式 I 的化合物 其中 R1 和 R2 各自为低级烷基、环（低级）烷基、低级烷氧基（低级）亚烷基、苯基或与低级烷基、低级烷氧基、卤代、硝基或三氟甲基单取代或二取代的苯基；或 RI 和 R2 共同形成-(CH2)m-X-(CH2)n-链，其中 m 和 n 均为 1 至 4 的整数，X 为亚甲基、氧杂环丁烷或硫杂环丁烷；或 R1 和 R2 与它们连接的碳原子共同形成螺-[1,2,3,4-四氢萘]-1 或螺[茚]-1 自由基；R3是氢或低级烷基；R'是氢、低级烷基、环（低级）烷基、苯基（低级）亚烷基、氨基（低级）亚烷基、低级烷基氨基（低级）亚烷基、二（低级烷基）氨基（低级）亚烷基或 3-吡啶基（低级）亚烷基，或其治疗上可接受的加成盐，这些化合物具有降血脂活性，可用于药物组合物中。 式 I 化合物可通过环化相应的式 X 化合物 并根据需要进行酯化。此外，还公开了四氢吡喃-2,3,5-三酮中间体。
• 31. A new and specific aromatisation reaction. Part II. Some further examples
  作者：P. A. Robins、James Walker

  DOI：10.1039/jr9570000177

  日期：——