allyl 1H-indole-1-carboxylate | 145291-79-8

• 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
• 英文名称: allyl 1H-indole-1-carboxylate
• 英文别名: indole-1-carboxylic acid allyl ester；Prop-2-enyl indole-1-carboxylate
• CAS: 145291-79-8
• 化学式: C₁₂H₁₁NO₂
• 分子量: 201.225
• InChiKey: HKYUKSHOLKTUAJ-UHFFFAOYSA-N

物化性质

• 沸点：
  316.3±35.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  allyl 1H-indole-1-carboxylate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 various solvent(s) 为溶剂， 反应 3.5h， 以75%的产率得到吲哚
  参考文献：
  名称：

  Chemoselective Radical Cleavage of Cbz-Protected Nitrogen Compounds

  摘要：

  [GRAPHICS]Tributylstannyl radicals promote the deprotection of N-Cbz derivatives of amides and nitrogen-containing heteroaromatic rings. These radical conditions do not affect N-Cbz derivatives of basic amines.

  DOI：

  10.1021/ol027495c
• 作为产物：
  描述：

  吲哚 、 (9ci)-1H-咪唑-1-羧酸-2-丙烯酯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以91%的产率得到allyl 1H-indole-1-carboxylate
  参考文献：
  名称：

  吲哚和恶唑烷酮与羰基唑类化合物的化学选择性N-酰化作用

  摘要：

  独特的反应性：在存在更多的反应性胺和醇官能团以及羧酸的情况下，吲哚和恶唑烷酮的化学选择性N-酰化是通过利用催化量为1的羰基唑酰化剂的独特反应性来实现的，8-二氮杂双环[5.4.0]十一月-7-烯（DBU）。

  DOI：

  10.1002/anie.201203976

文献信息

• ORGANIC COMPOUNDS
  申请人：Flachsmann Felix

  公开号：US20090036690A1

  公开（公告）日：2009-02-05

  The use of indole carbamates as fragrance ingredients and fragrance applications comprising indole carbamates in an effective amount.

  使用吲哚氨基甲酸酯作为香料成分以及包含有效量吲哚氨基甲酸酯的香料应用。
• Regioselective Inter- and Intramolecular Formal [4+2] Cycloaddition of Cyclobutanones with Indoles and Total Synthesis of (±)-Aspidospermidine
  作者：Mizuki Kawano、Takaaki Kiuchi、Shoko Negishi、Hiroyuki Tanaka、Takaya Hoshikawa、Jun-ichi Matsuo、Hiroyuki Ishibashi

  DOI：10.1002/anie.201206734

  日期：2013.1.14

  way: A formal [4+2] cycloaddition between various cyclobutanones and indoles proceeded efficiently under Lewis acid catalysis (see scheme; PG = protecting group). The regioselectivity of the reaction could be controlled in such a way that each of the two possible regioisomers of a cycloaddition product could be synthesized selectively. The usefulness of this reaction for the total synthesis of hydrocarbazole

  这种方式：在路易斯酸催化下，各种环丁酮和吲哚之间的正式[4 + 2]环加成反应有效进行（参见方案； PG =保护基）。可以以这样的方式控制反应的区域选择性，使得可以选择性地合成环加成产物的两种可能的区域异构体中的每一个。证明了该反应对于完全合成烃唑天然产物的有用性。
• Palladium-Catalyzed Decarboxylative Allylation and Benzylation of <i>N</i>-Alloc and <i>N</i>-Cbz Indoles
  作者：Thomas D. Montgomery、Ye Zhu、Natsuko Kagawa、Viresh H. Rawal

  DOI：10.1021/ol400334u

  日期：2013.3.1

  for the palladium-catalyzed decarboxylative C3-allylation and C3-benzylation of indoles, starting from the corresponding N-alloc and N-Cbz indoles, respectively, is reported. This chemistry provides ready access to a wide range of functionalized indolenines in good to excellent yields. A tandem process, wherein the palladium catalyzed allylation chemistry is coupled with a Mizoroki–Heck reaction, offers

  分别从相应的N- alloc 和N- Cbz 吲哚开始，钯催化的吲哚脱羧 C3-烯丙基化和 C3-苄基化的一组通用方法被报道。这种化学反应可以很容易地获得各种功能化的假吲哚，收率非常好。一种串联工艺，其中钯催化的烯丙基化化学与 Mizoroki-Heck 反应相结合，为肉桂化产品提供了一条简单的途径。
• Mild and selective deprotection of carbamates with Bu4NF
  作者：Ulrich Jacquemard、Valérie Bénéteau、Myriam Lefoix、Sylvain Routier、Jean-Yves Mérour、Gérard Coudert

  DOI：10.1016/j.tet.2004.07.071

  日期：2004.10

  A new mild method allowing the removal of carbamates using TBAF in THF is reported. Reactions were performed on indole, indoline, N-methyl aniline, aniline and tryptamine derivatives. The observed selectivity according to the carbamates or the substrates is discussed. A mechanism is postulated. (C) 2004 Published by Elsevier Ltd.
• Intramolecular Photochemical Cycloaddition Reactions of N-[(.omega.-Alkenyloxy)carbonyl]indoles and N-(.omega.-Alkenoyl)indoles
  作者：David L. Oldroyd、Alan C. Weedon

  DOI：10.1021/jo00085a022

  日期：1994.3

  Ultraviolet light irradiation of N-(but-3'-enoyl)indole (3i), N-(pent-4'-enoyl)indole (3j), and N-(hex-5'-enoyl) indole (3k) affords intramolecular photocycloadducts 17a-19a in which the termini of the side-chain alkene have become bonded to the 2- and 3-positions of the indole ring. The regiochemistry of the addition of the alkene is the opposite to that obtained in the corresponding intermolecular reaction of an N-acylindole with a monosubstituted alkene. The length of the methylene linkage between the tethered alkene and the N-acyl activating group in these N-alkenoylindoles affects the quantum efficiency of intramolecular cycloaddition as well as the ability of the reaction to compete with intermolecular cycloaddition in the presence of added cyclopentene. In contrast, the N-(omega-alkenyloxycarbonyl)indoles 3a-e are relatively photostable, apparently because they are frozen in an unreactive conformation for the duration of the excited state lifetime. Compounds 3a-e are, however, capable of undergoing intermolecular photocycloaddition in the presence of added alkenes and they also photodimerize. These reaction pathways dominate when lower energy wavelengths (lambda>300 nm) of ultraviolet light are used; irradiations performed at higher, energy wavelength (254 nm) give predominantly photo-Fries rearrangement products.