1-benzyl-5-methyl-1H-indole-3-carbaldehyde | 1134334-45-4

• 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
• 英文名称: 1-benzyl-5-methyl-1H-indole-3-carbaldehyde
• 英文别名: 1-benzyl-5-methylindole-3-carbaldehyde
• CAS: 1134334-45-4
• 化学式: C₁₇H₁₅NO
• mdl: MFCD12027458
• 分子量: 249.312
• InChiKey: DIFBXYXXTBILIQ-UHFFFAOYSA-N

物化性质

• 沸点：
  454.4±33.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  1-benzyl-5-methyl-1H-indole-3-carbaldehyde 在 正丁基锂 、 C₁₀₀H₁₁₂MgO₈P₂ 作用下， 以 四氢呋喃 、 正己烷 、 甲基环己烷 为溶剂， 反应 2.0h， 生成 (5aS,12aS,12bS)-12-benzyl-9-methyl-6,12,12a,12b-tetrahydro-5H-naphtho [2,3-a]carbazole-5,13(5aH)-dione
  参考文献：
  名称：

  苯醌和乙烯基吲哚与手性磷酸镁配合物的催化对映选择性Diels-Alder反应

  摘要：

  由于该支架在天然产物中的普遍存在及其在有机合成中的用途，因此四氢咔唑及其衍生物受到了广泛的关注。我们已经开发了由手性磷酸镁络合物催化的苯醌和3-乙烯基吲哚的Diels-Alder反应，从而以优异的收率和对映选择性（高达> 99％，99％ee）提供四氢咔唑衍生物。这种转化具有广泛的底物范围，出色的对映选择性和温和的条件。

  DOI：

  10.1021/acs.orglett.9b01437
• 作为产物：
  描述：

  5-甲基-1H-吲哚-3-甲醛 、 溴甲苯 在 四丁基硫酸氢铵 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成 1-benzyl-5-methyl-1H-indole-3-carbaldehyde
  参考文献：
  名称：

  苯醌和乙烯基吲哚与手性磷酸镁配合物的催化对映选择性Diels-Alder反应

  摘要：

  由于该支架在天然产物中的普遍存在及其在有机合成中的用途，因此四氢咔唑及其衍生物受到了广泛的关注。我们已经开发了由手性磷酸镁络合物催化的苯醌和3-乙烯基吲哚的Diels-Alder反应，从而以优异的收率和对映选择性（高达> 99％，99％ee）提供四氢咔唑衍生物。这种转化具有广泛的底物范围，出色的对映选择性和温和的条件。

  DOI：

  10.1021/acs.orglett.9b01437

文献信息

• Novel substituted (Z)-5-((N-benzyl-1H-indol-3-yl)methylene)imidazolidine-2,4-diones and 5-((N-benzyl-1H-indol-3-yl)methylene)pyrimidine-2,4,6(1H,3H,5H)-triones as potent radio-sensitizing agents
  作者：Y. Thirupathi Reddy、Konjeti R. Sekhar、Nidhish Sasi、P. Narsimha Reddy、Michael L. Freeman、Peter A. Crooks

  DOI：10.1016/j.bmcl.2009.11.082

  日期：2010.1

  A series of (Z)-5-((N-benzyl-1H-indol-3-yl)methylene)imidazolidine-2,4-dione (9a-9m) and 5-((N-benzyl-1H-indol-3-yl)methylene)pyrimidine-2,4,6(1H,3H,5H)-trione (10a-10i) derivatives that incorporate a variety of aromatic substituents in both the indole and N-benzyl moieties have been synthesized. These analogs were evaluated for their radiosensitization activity against the HT-29 cell line. Three analogs, 10a, 10b, and 10c were identified as the most potent radiosensitizing agents. (C) 2009 Elsevier Ltd. All rights reserved.
• Aplysinopsin analogs: Synthesis and anti-proliferative activity of substituted (Z)-5-(N-benzylindol-3-ylmethylene)imidazolidine-2,4-diones
  作者：Y. Thirupathi Reddy、P. Narsimha Reddy、Srinivas Koduru、Chendil Damodaran、Peter A. Crooks

  DOI：10.1016/j.bmc.2010.03.054

  日期：2010.5

  A series of substituted (Z)-5-(N-benzylindol-3-ylmethylene)imidazolidine-2,4-dione ( 3) analogs structurally related to aplysinopsin, and that incorporate a variety of substituents in both the indole and N-benzyl moieties have been synthesized under microwave irradiation and conventional heating methods These analogs were evaluated for their anti-proliferative activity against MCF-7 and MDA-231 breast cancer cell lines, and A549 and H460 lung cancer cell lines. Two analogs, 3f and 3j had IC50 values of 4.4 and 5.2 mu M, respectively, compared to 5-fluorouracil (IC50 = 15.2 mu M) against MCF-7 cells. (C) 2010 Elsevier Ltd. All rights reserved.
• Microwave assisted synthesis and in vitro cytotoxicities of substituted (Z)-2-amino-5-(1-benzyl-1H-indol-3-yl)methylene-1-methyl-1H-imidazol-4(5H)-ones against human tumor cell lines
  作者：Narsimha Reddy Penthala、Thirupathi Reddy Yerramreddy、Peter A. Crooks

  DOI：10.1016/j.bmcl.2009.11.083

  日期：2010.1

  The synthesis of several novel substituted (Z)-2-amino-5-(1-benzyl-1H-indol-3-yl)methylene-1-methyl-1H-imidazol-4(5H)-ones structurally related to aplysinopsin have been carried out under microwave irradiation and conventional heating methods. The analogs 3a, 3b, 3d-3g, 3k and 3l were evaluated for their in vitro cytotoxic activity against an NCI 60 human tumor cell line panel. Compound 3f exhibited good growth inhibitory properties against all but four of the human cancer cell lines examined, and afforded LC50 values < 10 mu M for 30% of the cell lines in the panel. Compound 3e was an effective inhibitor of leukemia, CNS, melanoma, and breast cancer cell growth, but generally less effective as a cytotoxic agent. Thus, the aplysinopsin analog 3f was regarded as a useful lead compound for further structural optimization. (C) 2009 Elsevier Ltd. All rights reserved.
• Catalytic Enantioselective Diels–Alder Reactions of Benzoquinones and Vinylindoles with Chiral Magnesium Phosphate Complexes
  作者：Yujia Bai、Jinping Yuan、Xiaoyue Hu、Jon C. Antilla

  DOI：10.1021/acs.orglett.9b01437

  日期：2019.6.21

  Tetrahydrocarbazole and its derivatives have received much attention due to the prevalence of this scaffold in natural products and their use in organic synthesis. We have developed a Diels–Alder reaction of benzoquinones and 3-vinylindoles catalyzed by chiral magnesium phosphate complexes to provide tetrahydrocarbazole derivatives in excellent yields and enantioselectivities (up to >99% yield, 99%

  由于该支架在天然产物中的普遍存在及其在有机合成中的用途，因此四氢咔唑及其衍生物受到了广泛的关注。我们已经开发了由手性磷酸镁络合物催化的苯醌和3-乙烯基吲哚的Diels-Alder反应，从而以优异的收率和对映选择性（高达> 99％，99％ee）提供四氢咔唑衍生物。这种转化具有广泛的底物范围，出色的对映选择性和温和的条件。