5-phenyl-5,6,7,8,9,10-hexahydrocyclohepta[b]indole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5-phenyl-5,6,7,8,9,10-hexahydrocyclohepta[b]indole
• 英文别名: 4-phenyl-1,2,3,4-tetrahydrocyclohepta[b]indole；5-Phenyl-5H,6H,7H,8H,9H,10H-cyclohepta[B]indole；5-phenyl-7,8,9,10-tetrahydro-6H-cyclohepta[b]indole
• 化学式: C₁₉H₁₉N
• mdl: MFCD02375791
• 分子量: 261.367
• InChiKey: ZWYGMNJERQJHTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  邻碘溴苯 在 tris(dibenzylideneacetone)dipalladium (0) sodium hexamethyldisilazane 、 sodium hydride 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 双(2-二苯基磷苯基)醚 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 42.0h， 生成 5-phenyl-5,6,7,8,9,10-hexahydrocyclohepta[b]indole
  参考文献：
  名称：

  钯催化的串联烯基和芳基C-N键的形成：级联N-环化成1-官能化吲哚的途径。

  摘要：

  DOI：

  10.1002/anie.200461598

文献信息

• Palladium-Catalyzed Annulation of Diarylamines with Olefins through CH Activation: Direct Access to N-Arylindoles
  作者：Upendra Sharma、Rajesh Kancherla、Togati Naveen、Soumitra Agasti、Debabrata Maiti

  DOI：10.1002/anie.201406284

  日期：2014.10.27

  A palladium‐catalyzed dehydrogenative coupling between diarylamines and olefins has been discovered for the synthesis of substituted indoles. This intermolecular annulation approach incorporates readily available olefins for the first time and obviates the need of any additional directing group. An ortho palladation, olefin coordination, and β‐migratory insertion sequence has been proposed for the

  已发现二芳基胺和烯烃之间的钯催化的脱氢偶联反应可用于合成取代的吲哚。这种分子间环化方法首次引入了容易获得的烯烃，从而消除了对任何其他导向基团的需要。一个邻 palladation，烯烃配位，和β-迁徙插入序列已经提出了产生的olefinated中间体，其被发现产生预期的吲哚部分。
• New imidazolylmethyl-cycloalkane(b)indolones
  申请人：DUPHAR INTERNATIONAL RESEARCH B.V

  公开号：EP0338650A1

  公开（公告）日：1989-10-25

  The invention relates to new imidazolylmethyl-cycloalka­ne[b]indolones having formula wherein - R₀ is alkyl or alkoxy having 1-4 C-atoms, hydroxy, halogen, trifluoromethyl, a group R₆R₇N or R₆R₇-N-CO, wherein R₆ and R₇ are hydrogen or alkyl having 1-4 C-­atoms or wherein R₆R₇N is a saturated 5-6 ring and n has the value 0, 1 or 2, - R₁ is hydrogen, 1-8 C alkyl, 3-7 C cycloalkyl, 3-7 C cycloalkyl-(1-3 C)- alkyl, 3-6 C alkenyl, 3-8 C alkynyl, phenyl or phenyl-(1-3 C) alkyl, wherein the phenyl group may be substituted with one or more alkyl groups, alkoxy groups or OH-groups or with one or more halogen atoms, or R₁ is a group COOR₈, COR₈, SO₂R₈, wherein R₈ is 1-4 C alkyl, 3-7 C cycloalkyl, phenyl or phenyl-(1-2 C)alkyl wherein the phenyl group may be substituted with one or more 1-4 C alkyl groups, 1-4 C alkoxy groups, hydroxyl groups or halogen atoms, or R₁ is a group R₉R₁₀N-C ⁰ wherein R₉ and R₁₀ independently of each other are hydrogen, 1-4 C alkyl, phenyl or phenyl-(1-2 C)alkyl wherein the phenyl group may be substituted, or wherein R₉ and R₁₀ together with the nitrogen atom to which they are bound constitute a saturated 5-6 ring, - one of the groups R₂, R₃ and R₄ is hydrogen, alkyl having 1-4 C atoms, cycloalkyl having 3-6 C-atoms, alkenyl having 2-4 C-atoms or phenyl-alkyl having 1-2 C-atoms in the alkyl group and the two other groups, independently of each other, are hydrogen or alkyl having 1-4 C-atoms, - m has the value 3 to 8 inclusive, and the pharmaceutically acceptable acid addition salts thereof. The compounds have a longer-lasting selective anta­gonistic activity on "neuronal" 5-hydroxytryptamine (5-HT) receptors as compared with related known compounds, and they are less toxic.

  该发明涉及新的咪唑基甲基-环烷[b]吲哚酮类化合物，其化学式为：其中，- R₀是具有1-4个碳原子的烷基或烷氧基，羟基，卤素，三氟甲基，R₆R₇N或R₆R₇-N-CO基团，其中R₆和R₇是氢或具有1-4个碳原子的烷基，或者R₆R₇N是饱和的5-6环，n的值为0，1或2，- R₁是氢，1-8个碳原子的烷基，3-7个碳原子的环烷基，3-7个碳原子的环烷基-(1-3个碳原子)-烷基，3-6个碳原子的烯基，3-8个碳原子的炔基，苯基或苯基-(1-3个碳原子)烷基，其中苯基可以被一个或多个烷基，烷氧基或羟基取代，或者被一个或多个卤素原子取代，或者R₁是COOR₈，COR₈，SO₂R₈基团，其中R₈是1-4个碳原子的烷基，3-7个碳原子的环烷基，苯基或苯基-(1-2个碳原子)烷基，其中苯基可以被一个或多个1-4个碳原子的烷基，1-4个碳原子的烷氧基，羟基或卤素原子取代，或者R₁是R₉R₁₀N-C ⁰基团，其中R₉和R₁₀彼此独立地是氢，1-4个碳原子的烷基，苯基或苯基-(1-2个碳原子)烷基，其中苯基可以被取代，或者R₉和R₁₀连同它们所结合的氮原子构成饱和的5-6环，- R₂，R₃和R₄中的一个是氢，具有1-4个碳原子的烷基，具有3-6个碳原子的环烷基，具有2-4个碳原子的烯基或具有1-2个碳原子的苯基-烷基，而另外两个基团独立地是氢或具有1-4个碳原子的烷基，- m的值为3到8，包括8，并且其药学上可接受的酸盐。这些化合物与相关已知化合物相比具有更持久的选择性拮抗“神经元”5-羟色胺（5-HT）受体的活性，并且毒性更低。
• Catalytic Cascade: Efficient Synthesis of Cyclohepta[b]indoles and Cyclohepta[b]indole‐Indoline Conjugates via RCM, Hydrogenation, and Acid‐Catalyzed Ring Expansion
  作者：Nabin Parui、Tirtha Mandal、Sandip Maiti、Jyotirmayee Dash

  DOI：10.1002/chem.202401059

  日期：——

  Efficient catalytic assembly for cyclohepta[b]indoles is achieved through sequential transformations: ring-closing metathesis, catalytic hydrogenation, and acid-catalyzed ring expansion. Ring closing metathesis (RCM) and hydrogenation of oxindoles yield spirocyclohexane-3-oxindoles. A subsequent spontaneous ring expansion-aromatization sequence, catalyzed by either Lewis or Brønsted acid, results in

  环庚[b]吲哚的有效催化组装是通过顺序转化实现的：闭环复分解、催化氢化和酸催化扩环。羟吲哚的闭环复分解（RCM）和氢化产生螺环己烷-3-羟吲哚。随后由路易斯或布朗斯台德酸催化的自发扩环芳构化序列产生环庚[ b ]吲哚或环庚[ b ]吲哚-二氢吲哚缀合物。
• Barluenga, Jose; Jimenez-Aquino, Agustin; Aznar, Fernando, Journal of the American Chemical Society, 2009, vol. 131, p. 4031 - 4041
  作者：Barluenga, Jose、Jimenez-Aquino, Agustin、Aznar, Fernando、Valdes, Carlos

  DOI：——

  日期：——
• The Azaallylic Anion as a Synthon for Pd-Catalyzed Synthesis of Heterocycles: Domino Two- and Three-Component Synthesis of Indoles
  作者：José Barluenga、Agustín Jiménez-Aquino、Carlos Valdés、Fernando Aznar

  DOI：10.1002/anie.200604407

  日期：2007.2.19