3-hydroxy-3-(4-(trifluoromethyl)phenyl)isoindolin-1-one | 1810-26-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 3-hydroxy-3-(4-(trifluoromethyl)phenyl)isoindolin-1-one
• 英文别名: 3-hydroxy-3-[4-(trifluoromethyl)phenyl]-2H-isoindol-1-one
• CAS: 1810-26-0
• 化学式: C₁₅H₁₀F₃NO₂
• 分子量: 293.245
• InChiKey: ORXXMYCWEGYESN-UHFFFAOYSA-N

物化性质

• 沸点：
  502.4±50.0 °C(Predicted)
• 密度：
  1.436±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-hydroxy-3-(4-(trifluoromethyl)phenyl)isoindolin-1-one 在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.08h， 以1.15 g的产率得到3-(4-(trifluoromethyl)phenyl)isoindolin-1-one
  参考文献：
  名称：

  Fused Piperidines as a Novel Class of Potent and Orally Available Transient Receptor Potential Melastatin Type 8 (TRPM8) Antagonists

  摘要：

  The transient receptor potential melastatin type 8 (TRPM8) is a nonselective cation channel primarily expressed in a subpopulation of sensory neurons that can be activated by a wide range of stimuli, including menthol, icilin, and cold temperatures (< 25 degrees C). Antagonism of TRPM8 is currently under investigation as a new approach for the treatment of pain. As a result of our screening efforts, we identified tetrahydrothienopyridine 4 as an inhibitor of icilin-induced calcium influx in CHO cells expressing recombinant rat TRPM8. Exploration of the structure-activity relationships of 4 led to the identification of a potent and orally bioavailable TRPM8 antagonist, tetrahydroisoquinoline 87. Compound 87 demonstrated target coverage in vivo after oral administration in a rat pharmacodynamic model measuring the prevention of icilin-induced wet-dog shakes (WDS).

  DOI：

  10.1021/jm2013634
• 作为产物：
  描述：

  对溴三氟甲苯 在 碘 、 二异丁基氢化铝 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 3-hydroxy-3-(4-(trifluoromethyl)phenyl)isoindolin-1-one
  参考文献：
  名称：

  EP3750885

  摘要：

  公开号：

文献信息

• Organocatalytic Synthesis of α-Triphenylmethylamines from Diarylketimines and Phenols
  作者：Danijel Glavač、Nikola Topolovčan、Matija Gredičak

  DOI：10.1021/acs.joc.0c02225

  日期：2020.11.6

  formal Betti reaction between variously substituted phenols and benzophenone-derived imines to afford α-triphenylmethylamines is reported. The key to the success of this transformation is the in situ generation of the reactive benzophenone iminium species under organocatalytic conditions. Different phenols reacted smoothly, enabling the synthesis of an array of α-triphenylmethylamines, which are highly

  据报道，在各种取代的苯酚和二苯甲酮衍生的亚胺之间进行正式的Betti反应，得到α-三苯甲胺。该转化成功的关键是在有机催化条件下原位生成反应性二苯甲酮亚胺。不同的苯酚反应平稳，可以合成一系列α-三苯甲胺，这是生物活性分子和化学传感器中极有价值的结构图案。
• Chiral Brønsted acid-catalysed enantioselective synthesis of isoindolinone-derived N(acyl),S-acetals
  作者：Josipa Suć、Irena Dokli、Matija Gredičak

  DOI：10.1039/c5cc08813e

  日期：——

  Chiral Brønsted acid catalyzed synthesis of N(acyl),S-acetals from in situ generated ketimines proceeds in high yields and enantioselectivities.

  手性Brønsted酸催化的合成，从现场生成的酮亚胺中生成N(酰),S-缩醛，产率高，对映选择性好。
• Chiral phosphoric acid catalyzed enantioselective addition of thiols to in situ generated ketimines: Synthesis of N , S -ketals
  作者：Rajshekhar A. Unhale、Nagaraju Molleti、Nirmal K. Rana、Sivasankaran Dhanasekaran、Subhrajyoti Bhandary、Vinod K. Singh

  DOI：10.1016/j.tetlet.2016.11.114

  日期：2017.1

  The chiral Brønsted acid catalyzed enantioselective 1,2-addition of thiols to in situ generated ketimines, derived from 3-hydroxyisoindolinones, has been studied. The protocol provides a variety of isoindolinone-derived N,S-ketals in up to 98% yield and up to 99% enantioselectivity. The products have been converted to a known non-nucleoside HIV-1 reverse transcriptase inhibitor and a 1,3-thiazine derivative

  研究了手性布朗斯台德酸催化硫醇对映体选择性1,2-加成到原位生成的3-亚甲基异吲哚啉酮酮中。该方案以高达98％的收率和高达99％的对映选择性提供了各种异吲哚啉酮衍生的N，S-缩酮。产物已转化为已知的非核苷HIV-1逆转录酶抑制剂和1,3-噻嗪衍生物。
• Synthesis of Functionalized Isoindolinones via Calcium Catalyzed Generation and Trapping of <i>N</i>-Acyliminium Ions
  作者：Ashley J. Basson、Mark G. McLaughlin

  DOI：10.1021/acs.joc.0c00482

  日期：2020.4.17

  Herein we report our full investigation into the calcium catalyzed generation and trapping of N-acyliminium ions from readily available 3-hydroxyisoindolinones. We have successfully employed a range of traditional nucleophiles including carbon, nitrogen, and sulfur containing reactive partners. The reaction is tolerant to a wide range of functionalities and provides high value scaffolds in good to

  本文中，我们报告了对钙催化的生成和从易得的3-羟基异吲哚满酮中捕获N-酰基亚胺离子的全面研究。我们已经成功地使用了一系列传统的亲核试剂，包括含碳，氮和硫的反应性伙伴。该反应可耐受多种功能，并以高至优异的产率提供高价值的支架。
• Organocatalytic Synthesis of α,α–Diaryl Substituted α–Amino Acid Derivatives by an Interrupted Three-Component Ugi Reaction
  作者：Danijel Glavač、Ivanka Jerić、Matija Gredičak

  DOI：10.5562/cca3536

  日期：——

  An organocatalytic interrupted three-component Ugi reaction for the synthesis of α,α–diaryl α–amino acid derivatives is described. The transformation proceeds with a range of isocyanides and 3-aryl isoindolinone alcohols using Brønsted acid catalysts to afford products in good to excellent yields. Based on the obtained results, a reaction mechanism is proposed and discussed.

  描述了有机催化间断三组分Ugi反应，用于合成α，α-二芳基α-氨基酸衍生物。使用布朗斯台德酸催化剂，用一系列异氰化物和3-芳基异吲哚啉酮醇进行转化，从而以良好或优异的收率得到产物。基于获得的结果，提出并讨论了反应机理。