1-Phenylisoindoline | 35392-51-9

• 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: 1-Phenylisoindoline
• 英文别名: 1-Phenyl-isoindolin；1-Phenyl-2,3-dihydro-1H-isoindole
• CAS: 35392-51-9
• 化学式: C₁₄H₁₃N
• 分子量: 195.264
• InChiKey: AKVCHYGHEAZANX-UHFFFAOYSA-N

物化性质

• 熔点：
  53-55 °C
• 沸点：
  312.0±11.0 °C(Predicted)
• 密度：
  1.092±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-quinuclidin-3-yl carbonochloridate hydrochloride 、 1-Phenylisoindoline 在 吡啶 作用下， 以60%的产率得到1-Phenyl-1,3-dihydro-isoindole-2-carboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester
  参考文献：
  名称：

  Synthesis and Antimuscarinic Properties of Quinuclidin-3-yl 1,2,3,4-Tetrahydroisoquinoline-2-carboxylate Derivatives as Novel Muscarinic Receptor Antagonists

  摘要：

  In the course of continuing efforts to develop potent and bladder-selective muscarinic M-3 receptor antagonists, quinuclidin-3-yl 1-aryl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate derivatives and related compounds were designed as conformationally restricted analogues of quinuclidin-3-yl benzhydrylcarbamate (8). Binding assays with rat muscarinic receptor subtypes revealed that the quinuclidin-3-yl 1-aryl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate derivatives showed high affinities for the M3 receptor, and selectivity for the M3 receptor over the M-2 receptor. Of these derivatives, (+)-(1S,3'R)-quinuclidin-3'-yl 1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate monohydrochloride (9b) exhibited almost the same inhibitory activity against bladder contraction to that of oxybutynin (1), and more than 10-fold selectivity for bladder contraction versus salivary secretion, demonstrating that 9b may be useful for the treatment of symptoms associated with overactive bladder without having side effects such as dry mouth.

  DOI：

  10.1021/jm050099q
• 作为产物：
  描述：

  2-Aminomethyl-5-chlorbenzhydrol 在 4-二甲氨基吡啶 、 氢溴酸 、 锌 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 生成 1-Phenylisoindoline
  参考文献：
  名称：

  A novel rearrangement forming 4,5,6,11-tetra-hydrobenzo[6,7]cycloocta[1,2-b]thiophen-6,11-imines

  摘要：

  DOI：

  10.1016/s0040-4039(01)93742-6

文献信息

• Synthesis of tetra-substituted imidazoles and 2-imidazolines by Ni(0)-catalyzed dehydrogenation of benzylic-type imines
  作者：Adrian Tlahuext-Aca、Oscar Hernández-Fajardo、Alma Arévalo、Juventino J. García

  DOI：10.1039/c4dt02313g

  日期：——

  performed to yield asymmetrical tetra-substituted imidazoles and 2-imidazolines. This was achieved with a single operational step while maintaining good selectivity and atom economy. The catalytic system shows low to moderate tolerance for fluoro-, trifluoromethyl-, methyl-, and methoxy-substituted benzylic-type imines. In addition, the substitution pattern at the N-heterocyclic products was easily

  Ni（0）催化的苄型亚胺脱氢反应可制得不对称的四取代的咪唑和2-咪唑啉。这是通过一个单一的操作步骤即可实现的，同时保持了良好的选择性和原子经济性。催化体系对氟，三氟甲基，甲基和甲氧基取代的苄基亚胺具有低至中等的耐受性。另外，通过适当地选择起始有机底物中的R-基团，可以容易地控制N-杂环产物上的取代模式。基于实验观察，我们提出了一种反应机理，其中苄基C（sp 3）–H键的活化和插入步骤在该镍催化的有机转化中起关键作用。
• High affinity small molecule C5a receptor modulators
  申请人：Thurkauf Andrew

  公开号：US20070027158A1

  公开（公告）日：2007-02-01

  This invention relates to low molecular weight, non-peptidic, non-peptidomimetic, organic molecules that act as modulators of mammalian complement C5a receptors, preferably ones that act as high affinity C5a receptor ligands and also to such ligands that act as antagonists or inverse agonists of complement C5a receptors. Preferred compounds of the invention possess some or all of the following properties in that they are: 1) multi-aryl in structure, 2) heteroaryl in structure, 3) a pharmaceutically acceptable oral dose can provide a detectable in vitro effect, 4) comprise fewer than four or preferably no amide bonds, and 5) capable of inhibiting leukocyte chemotaxis at nanomolar or sub-nanomolar concentrations. This invention also relates to pharmaceutical compositions comprising such compounds and the use of such compounds in treating a variety of inflammatory and immune system disorders. Additionally, this invention relates to the use such compounds as probes for the localization of C5a receptors.

  本发明涉及低分子量、非肽、非肽类似物有机分子，其作为哺乳动物补体C5a受体的调节剂。其中，优选的化合物是作为高亲和力C5a受体配体的，也是作为补体C5a受体的拮抗剂或反向激动剂的。该发明的优选化合物具有以下一些或全部特性：1）多芳基结构，2）杂芳基结构，3）药学上可接受的口服剂量可提供可检测的体外效果，4）包含少于四个或优选不含酰胺键，5）能够在纳摩尔或亚纳摩尔浓度下抑制白细胞趋化。此外，本发明还涉及包括这些化合物的制药组合物，以及将这些化合物用于治疗各种炎症和免疫系统疾病的用途。此外，本发明还涉及将这些化合物用作C5a受体定位的探针的用途。
• Process for preparing diphenylalkene derivatives
  申请人：KANZAKI PAPER MANUFACTURING CO., LTD.

  公开号：EP0257591A2

  公开（公告）日：1988-03-02

  A process for preparing a diphenylalkene derivative of the formula [II] which comprises oxidizing a diphenylalkanoic acid derivative of the formula [I] wherein R₁ and R₂ are each substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aralkyl or substituted or unsubstituted aryl, R₁ and R₂ may form a heteroring together therewith or with an adjacent benzene ring, R₃, R₄, R₅, R₆, R₇, R₈, R₉, R₁₀ and R₁₁ are each hydrogen atom, halogen atom, substituted or unsubstituted alkyl, substituted or unsubstituted hydroxyl or substituted or unsubstituted amino, R₁₂ and R₁₃ are each hydrogen atom or substituted or unsubstituted alkyl, X is carboxyl, amide, ester or halide thereof.

  一种制备式[II]二苯基烷烃衍生物的工艺 其中包括氧化式[I]的二苯基烷酸衍生物 其中 R₁ 和 R₂ 各自为取代或未取代的烷基、取代或未取代的烯基、取代或未取代的炔基、取代或未取代的环烷基、取代或未取代的芳烷基或取代或未取代的芳基，R₁ 和 R₂ 可与之或与相邻的苯环一起形成杂环、R₃、R₄、R₅、R₆、R₇、R₈、R₉、R₁₀ 和 R₁₁ 各为氢原子、卤素原子、取代或未取代的烷基、取代或未取代的羟基或取代或未取代的氨基，R₁₂ 和 R₁₃ 各为氢原子或取代或未取代的烷基，X 为羧基、酰胺、酯或其卤化物。
• NOVEL QUINUCLIDINE DERIVATIVES AND MEDICINAL COMPOSITION THEREOF
  申请人：YAMANOUCHI PHARMACEUTICAL CO. LTD.

  公开号：EP0801067B1

  公开（公告）日：2003-03-05
• ROBINSON, RALPH P.;DONAHUE, KATHLEEN M.;SACCOMANO, NICHOLAS A., TETRAHEDRON LETT., 30,(1989) N9, C. 5203-5206
  作者：ROBINSON, RALPH P.、DONAHUE, KATHLEEN M.、SACCOMANO, NICHOLAS A.

  DOI：——

  日期：——