1-(3-氯丙基)吲哚-3-甲醛 | 156237-48-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 1-(3-氯丙基)吲哚-3-甲醛
• 英文名称: 1-(3-Chloropropyl)indole-3-carboxaldehyde
• 英文别名: 1-(3-Chloropropyl)indole-3-carbaldehyde
• CAS: 156237-48-8
• 化学式: C₁₂H₁₂ClNO
• 分子量: 221.686
• InChiKey: YYPSZNRKRTUESL-UHFFFAOYSA-N

物化性质

• 沸点：
  389.6±22.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(3-氯丙基)吲哚-3-甲醛 在 sodium azide 、 sodium hydride 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 1-(2-氯乙基)-1H-吲哚-3-甲醛
  参考文献：
  名称：

  Synthesis of tricyclic-2-aminoindoles by intramolecular 1,3-dipolar cycloaddition of 1-ω-azidoalkylindoles

  摘要：

  Thermolysis of the 1-omega -azidoalkylindoles 4, bearing an electron attracting substituent at C-3 (CHO, COMe, COOMe, CN) provides imidazo[1,2-a]indoles (5, n = 1), pyrimidino[1,2-a]indoles (5, n = 2), and 1,3-diazepino[1,2-a]indoles (5, n = 3). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01006-1
• 作为产物：
  描述：

  1-(4-氯丁基)吲哚-3-甲醛 在 sodium azide 、 sodium hydride 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 1-(3-氯丙基)吲哚-3-甲醛
  参考文献：
  名称：

  Synthesis of tricyclic-2-aminoindoles by intramolecular 1,3-dipolar cycloaddition of 1-ω-azidoalkylindoles

  摘要：

  Thermolysis of the 1-omega -azidoalkylindoles 4, bearing an electron attracting substituent at C-3 (CHO, COMe, COOMe, CN) provides imidazo[1,2-a]indoles (5, n = 1), pyrimidino[1,2-a]indoles (5, n = 2), and 1,3-diazepino[1,2-a]indoles (5, n = 3). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01006-1

文献信息

• Synthesis of 1,2-fused indoles by radical cyclisation
  作者：Christopher J. Moody、Claire L. Norton

  DOI：10.1016/0040-4039(95)01909-2

  日期：1995.12

  Treatment of the 1-(ω-iodoalkyl)indole-3-carboxaldehydes 8–13 with tributyltin hydride and AIBN results in radical cyclisation with oxidation to give the 1,2-fused indoles 14–19.

  用氢化三丁基锡和AIBN处理1-（ω-碘烷基）吲哚-3-羧醛8-13会导致自由基环化并氧化，得到1,2-稠合的吲哚14-19。
• Catalyst- and Substituent-Controlled Regio- and Stereoselective Synthesis of Indolyl Acrylates by Lewis-Acid-Catalyzed Direct Functionalization of 3-Formylindoles with Diazo Esters
  作者：Sana Jamshaid、Shreedhar Devkota、Yong Rok Lee

  DOI：10.1021/acs.orglett.1c00277

  日期：2021.3.19

  A facile and efficient In(OTf)3- and BF3·OEt2-catalyzed direct transformation of 3-formylindoles with diazo esters has been developed for synthesizing diverse and functionalized indolyl acrylates. This one-pot protocol furnishes various (Z)-α-hydroxy-β-indolyl acrylates, (E)-β-(2-alkoxy-2-oxoethoxy)-α-indolyl acrylates, and (Z)-3-hydroxy-2-indolyl acrylates by a catalyst- and substituent-controlled

  已开发了一种重氮化合物，可以轻松，高效地用In（OTf）3-和BF 3 ·OEt 2催化3-甲酰基吲哚的直接转化，以合成各种功能化的丙烯酸吲哚酯。此一锅操作方案可提供各种（Z）-α-羟基-β-吲哚基丙烯酸酯，（E）-β-（2-烷氧基-2-氧代乙氧基）-α-吲哚基丙烯酸酯和（Z）-3-羟基-丙烯酸酯丙烯酸2-吲哚基酯通过催化剂和取代基控制的区域和立体选择性级联反应。该方案具有几个优点，包括催化剂的低负载，温和的反应条件，范围宽和官能团耐受性高。合成的化合物可以进一步转化为多种功能化的材料。
• Moody, Christopher J.; Norton, Claire L., Journal of the Chemical Society. Perkin transactions I, 1997, # 17, p. 2639 - 2643
  作者：Moody, Christopher J.、Norton, Claire L.

  DOI：——

  日期：——
• Oxidative Radical Cyclization of (.omega.-Iodoalkyl)indoles and Pyrroles. Synthesis of (-)-Monomorine and Three Diastereomers
  作者：Dean R. Artis、In-Seop Cho、Saul Jaime-Figueroa、Joseph M. Muchowski

  DOI：10.1021/jo00088a029

  日期：1994.5

  Addition of excess hydrogen peroxide (10 equiv) to a sonicated solution of FeSO4:7H(2)O (1 equiv) in Dh ISO containing the N-(omega-iodoalkyl)indoles 4, 5, 11, and 13 effected oxidative radical cyclization to 6, 7, 14, and 15, respectively. The (omega-iodoalkyl)pyrroles 21, 22, 27, 38, and 49 underwent analogous cyclization reactions to 23, 24, 28, 39, and 50, respectively. The regiochemistry of these radical cyclization reactions was correctly predicted by FMO calculations in all cases but one. For compound 38, FMO calculations indicated that radical attack should take place at both C-3 and C-5. Only the product of cyclization at C-5, i.e., 39, was observed. The enantiomerically pure bicyclic ketone 42, prepared by the above technique from the iodide 53, was converted into 55 which, on catalytic reduction (H-2/Rh-A1(2)O(3)), gave a mixture of (-)-monomorine (40) and three of its diastereomers 56-58 (see, however, Note Added in Proof).
• PYRROLOINDOLES, PYRIDOINDOLES AND AZEPINOINDOLES AS 5-HT2C AGONISTS
  申请人：VERNALIS RESEARCH LIMITED

  公开号：EP1109813A1

  公开（公告）日：2001-06-27