1,5-dihydrobenzindol-4(3H)-one | 2731-96-6

• 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: 1,5-dihydrobenzindol-4(3H)-one
• 英文别名: 3,5-dihydrobenzo[cd]indol-4(1H)-one；1,3,4,5-tetrahydrobenz[cd]indole-4-one；2-Azatricyclo[6.3.1.0,4,12]dodeca-1(11),3,8(12),9-tetraen-6-one；3,5-dihydro-1H-benzo[cd]indol-4-one
• CAS: 2731-96-6
• 化学式: C₁₁H₉NO
• 分子量: 171.199
• InChiKey: OHFYTXXSEKNWQH-UHFFFAOYSA-N

物化性质

• 熔点：
  146-147 °C (decomp)
• 沸点：
  407.7±45.0 °C(Predicted)
• 密度：
  1.343±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,5-dihydrobenzindol-4(3H)-one 在 sodium tetrahydroborate 作用下， 以99%的产率得到4-hydroxy-1,3,4,5-tetrahydrobenzindole
  参考文献：
  名称：

  Syntheses of (±)-4-Amino-1,3,4,5-tetrahydrobenz[cd]indole-4-carboxylic Acid, (±)-4-N,N-Dipropylamino-4-hydroxymethyl- and (±)-4-Propyloxy-1,3,4,5-tetrahydrobenz[cd]indole

  摘要：

  Simple syntheses of the title compounds are reported starting from indole-3-carboxaldehyde.

  DOI：

  10.3987/com-94-6738
• 作为产物：
  描述：

  4-(2-nitroethenyl)-1H-indole 在 乙酸铵 、 sodium tetrahydroborate 、 titanium(III) chloride 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.66h， 生成 1,5-dihydrobenzindol-4(3H)-one
  参考文献：
  名称：

  Ergoline synthons. 2. Synthesis of 1,5-dihydrobenz[cd]indol-4(3H)-ones and 1,3,4,5-tetrahydrobenz[cd]indol-4-amines

  摘要：

  DOI：

  10.1021/jo00199a004

文献信息

• Biarylphosphonite Gold(I) Complexes as Superior Catalysts for Oxidative Cyclization of Propynyl Arenes into Indan-2-ones
  作者：Guilhem Henrion、Thomas E. J. Chavas、Xavier Le Goff、Fabien Gagosz

  DOI：10.1002/anie.201301015

  日期：2013.6.10

  Striking gold: A series of variously functionalized propynyl arenes was smoothly converted into indan‐2‐ones by a new gold(I)‐catalyzed oxidative cyclization process. [LAu]NTf2 (Tf=trifluoromethanesulfonyl) is a superior catalyst both in terms of yield and kinetics for the present transformation.

  打击金：通过新的金（I）催化的氧化环化工艺，一系列功能化的丙炔基芳烃被顺利转化为茚满-2-酮。就本转化而言，就收率和动力学而言，[ L Au] NTf 2（Tf ＝三氟甲磺酰基）是优良的催化剂。
• New compounds
  申请人：Angbrant Joean

  公开号：US20080032968A1

  公开（公告）日：2008-02-07

  The present invention relates to novel compounds of formula (I): wherein m, n, R 0 , R 1 , R 2 , R 3 and R 4 are as described herein, to pharmaceutical compositions comprising the compounds, to processes for their preparation, as well as to the use of the compounds for the preparation of a medicament against 5-HT 6 receptor-related disorders.

  本发明涉及公式（I）的新化合物：其中m，n，R0，R1，R2，R3和R4如本文所述，以及包含这些化合物的制药组合物，用于它们的制备过程，以及用于制备针对5-HT6受体相关疾病的药物的化合物的用途。
• Synthesis of 4-Amino-, 4-Hydroxy-, and 4-Nitro-1,3,4,5-tetrahydrobenz[cd]indols and Its Bromination
  作者：Masanori Somei、Kyoko Nakagawa、Naokatsu Aoki、Harunobu Mukaiyama

  DOI：10.3987/com-13-s(s)74

  日期：——

  Simple synthetic method for 4-nitro-1,3,4,5-tetrahydrobenz[cd]indole (6) is established from indole-3-carboxaldehyde (7). With 6 in hand, various derivatives of 4-amino-, 4-hydroxy- and 4-amino-4-hydroxymethyl-1,3,4,5-tetrahydrobenz[cd]indoles become readily available. Bromination of 6 afforded useful building blocks for further manipulation. Successful optical resolution of 6 by chiral column chromatography is also reported.
• KRUSE, L. I.;MEYER, M. D., J. ORG. CHEM., 1984, 49, N 25, 4761-4768
  作者：KRUSE, L. I.、MEYER, M. D.

  DOI：——

  日期：——
• INDOLES AS 5-HT6 MODULATORS
  申请人：Proximagen Ltd.

  公开号：EP2046741B1

  公开（公告）日：2012-10-31