ethyl 3H-benzo[e]indole-2-carboxylate | 52280-52-1

• 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: ethyl 3H-benzo[e]indole-2-carboxylate
• 英文别名: 3H-benzo[e]indole-2-carboxylic acid ethyl ester；3H-benz[e]indole-2-carboxylic acid ethyl ester；3H-Benz[e]indol-2-carbonsaeure-aethylester；ethyl benz[e]indole-2-carboxylate
• CAS: 52280-52-1
• 化学式: C₁₅H₁₃NO₂
• mdl: MFCD11458092
• 分子量: 239.274
• InChiKey: MZNWVDAWTJDZLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 3H-benzo[e]indole-2-carboxylate 在 喹啉 、 铜 、 sodium cyanoborohydride 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 33.0h， 生成 3H-benzo[e]indoline
  参考文献：
  名称：

  3H-苯并[e]二氢吲哚的合成及其在小分子有机太阳能电池中的应用

  摘要：

  合成了带有3 H-苯并[e]二氢吲哚的基于方酸的小分子（USQ-BI），相应的有机太阳能电池显示了5.35％的功率转换效率，且短路电流超过15 mA厘米-2。USQ-BI的空穴迁移率是基于吲哚啉的方酸的约5倍（9.57×10 -5与2.00×10 -5  cm 2  V -1  s -1）。

  DOI：

  10.1002/chem.201800938
• 作为产物：
  描述：

  ethyl 4-chloro-3H-benzindole-2-carboxylate 在 palladium on activated charcoal 氢气 、 calcium oxide 作用下， 以 乙醇 为溶剂， 反应 13.0h， 以0.009 g的产率得到ethyl 3H-benzo[e]indole-2-carboxylate
  参考文献：
  名称：

  Ishii, Hisashi; Murakami, Yasuoki; Watanabe, Toshiko, Journal of Chemical Research, Miniprint, 1984, # 10, p. 2974 - 2997

  摘要：

  DOI：

文献信息

• CBI analogues of the duocarmycins and CC-1065
  申请人：Boger L. Dale

  公开号：US20050026987A1

  公开（公告）日：2005-02-03

  An extensive series of CBI analogues of the duocarmycins and CC-1065 exploring substituent effects within the first indole DNA binding subunit is detailed. In general, substitution at the indole C5 position led to cytotoxic potency enhancements that can be ≧1000-fold providing simplified analogues containing a single DNA binding subunit that are more potent (IC 50 =2-3 pM) than CBI-TMI, duocarmycin SA, or CC-1065. The increases in cytotoxicity correlate well with accompanying increases in the rate and efficiency of DNA alkylation. This effect is more pronounced with the CBI versus DSA or CPI based analogues. Moreover, this effect is largely insensitive to the electronic character of the C5 substituent but is sensitive to the size, rigid length, and shape (sp, sp 2 , sp 3 hybridization) of this substituent consistent with expectation that the impact is due simply to its presence.

  一系列广泛的CBI类似物，包括二聚卡蜜素和CC-1065的类似物，探索了第一个吲哚DNA结合亚基中取代基效应的细节。一般来说，在吲哚C5位置的取代导致细胞毒性增强，可以达到≧1000倍，提供了更强效（IC50=2-3 pM）的含有单个DNA结合亚基的简化类似物，比CBI-TMI、二聚卡蜜素SA或CC-1065更有效。细胞毒性增加与DNA烷基化速率和效率的增加密切相关。与基于DSA或CPI的类似物相比，这种效应在CBI类似物中更为显著。此外，这种效应对于C5取代基的电子性质不太敏感，但对于取代基的大小、刚性长度和形状（sp、sp2、sp3杂化）敏感，这与预期一致，即这种影响仅仅是由于其存在。
• Synthetic Studies on Indoles and Related Compounds. XXIX. Attempted Syntheses of Benz(f)indoles by Cyclization Reactions.
  作者：Toshiko WATANABE、Hiroyuki TAKAHASHI、Hiroyuki KAMAKURA、Susumu SAKAGUCHI、Masako OSAKI、Satoru TOYAMA、Yuka MIZUMA、Ikuko UEDA、Yasuoki MURAKAMI

  DOI：10.1248/cpb.39.3145

  日期：——

  Syntheses of benz[f]indoles from 1, 2-disubstituted naphthalene derivatives by means of cyclization reactions were attempted. The Fischer indolization of 1-methyl-(5a), 1-chloro-(5b), or 1-nitro-(5c)-2-naphthylhydrazones gave only benz[e]indole derivative or decomposed products, and the desired 9-substituted benz[f]indole (3) was not produced. On the other hand, the Fischer indolization of 2-methoxy-1-naphthylhydrazone (17) gave ethyl 5-chlorobenz[g]indole-2-carboxylate (19). The hemetsberger reaction of 1-methyoxy-2-naphthylazido acrylate (26a) gave an azirine (28a) and a nitrile (29a), whereas the same reaction of 1-chloro-2-naphthylazido acrylate (26b) gave the desired 4-chlorobenz[f]indole in a poor yield together with large amounts of by-products, the azirine (28b), the nitrile (29b) and the benz[g]indole (20). These results show that cyclization reactions of a 2-substituent toward the 3-position in naphthalene derivative are not suitable for preparing benz[f]indoles.

  尝试通过环化反应从1,2-二取代的萘衍生物合成苯并[f]吲哚。1-甲基-(5a)、1-氯-(5b)或1-硝基-(5c)-2-萘基苯肼经Fischer吲哚合成法只得到苯并[e]吲哚衍生物或分解产物，未得到期望的9-取代苯并[f]吲哚(3)。另一方面，2-甲氧基-1-萘基苯肼(17)经Fischer吲哚合成法得到乙基5-氯苯并[g]吲哚-2-羧酸酯(19)。1-甲氧基-2-萘基叠氮丙烯酸酯(26a)的Hemetsberger反应得到氮杂环丙烷(28a)和腈(29a)，而同样的反应1-氯-2-萘基叠氮丙烯酸酯(26b)得到产率低的期望4-氯苯并[f]吲哚以及大量副产物，氮杂环丙烷(28b)、腈(29b)和苯并[g]吲哚(20)。这些结果表明，萘衍生物2-取代基向3-位置的环化反应不适合用于制备苯并[f]吲哚。
• Microwave-assisted synthesis of indole-2-carboxylic acid esters in ionic liquid
  作者：Lijun Gu、Xiangguang Li

  DOI：10.1590/s0103-50532011001100003

  日期：——

  An improved procedure for the synthesis of indole-2-carboxylic acid esters in excellent yields has been achieved by the condensation of 2-halo aryl aldehydes or ketones and ethyl isocyanoacetate using ionic liquid under controlled microwave irradiation (100 W) at 50 °C. This method offers a number of advantages in terms of methodology, high-product yield, short period of conversion, mild reaction conditions

  在控制微波辐射（100 W）和50°C的条件下，使用离子液体将2-卤代芳基醛或酮与异氰基乙酸乙酯缩合，从而实现了以优异的产率合成吲哚-2-羧酸酯的改进方法。该方法在方法学，高产物收率，短转化时间，温和的反应条件和易于后处理方面具有许多优点。
• ZrCl₄-promoted facile synthesis of indole derivatives
  作者：J. Tummatorn、M. P. Gleeson、S. Krajangsri、C. Thongsornkleeb、S. Ruchirawat

  DOI：10.1039/c4ra02158d

  日期：——

  Zirconium(iv) chloride effectively activates nitrogen (N₂) extrusion from aryl azidoacrylates followed by annulation to provide the desired indole products in moderate to good yields.

  锆（IV）氯化物有效地激活芳基叠氮丙烯酸酯中的氮（N2）挤出，随后进行环化反应，以中等至良好的产率提供所需的吲哚产物。
• 543. Experiments on the synthesis of Bz-substituted indoles and tryptophans. Part II. Attempted syntheses of Bz-nitro-indoles and -tryptophans. the synthesis of 5-ethoxytryptophan and of 4 : 5- and 6 : 7-benzotryptophan
  作者：H. N. Rydon、S. Siddappa

  DOI：10.1039/jr9510002462

  日期：——