(3E)-3-ethylidene-1-methyl-1,3-dihydro-2H-indol-2-one | 58807-96-8

• 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: (3E)-3-ethylidene-1-methyl-1,3-dihydro-2H-indol-2-one
• 英文别名: (E)-ethyl 2-(1-methyl-2-oxoindolin-3-ylidene)acetate；(E)-3-ethylindene-1-methylindolin-2-one；(E)-3-ethylidene-1-methylindolin-2-one；trans-N-methyl-3-ethylideneoxindole；(3E)-3-ethylidene-1-methylindol-2-one
• CAS: 58807-96-8
• 化学式: C₁₁H₁₁NO
• 分子量: 173.214
• InChiKey: TVPDOFVCIQFJJA-FPYGCLRLSA-N

物化性质

• 沸点：
  272.1±20.0 °C(Predicted)
• 密度：
  1.208±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3E)-3-ethylidene-1-methyl-1,3-dihydro-2H-indol-2-one 在 palladium hydroxide, 20 wt% on carbon 、 氢气 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 51.0h， 生成
  参考文献：
  名称：

  Total Synthesis of Maremycins A and D1 Using Chiral and Cyclic Nitrone with (E)-3-Ethylidene-1-methylindolin-2-one

  摘要：

  Total syntheses of maremycin A (4) and maremycin D, (8) were described, featuring 1,3-dipolar cycloaddition of a chiral cyclic nitrone 15 with (E)-3-ethylidene-1-methylindolin-2-one (13). The cycloaddition was reversible, especially at high temperature in the presence of a Lewis acid or in a solvent possessing a high acceptor number. One of the cycloadducts was efficiently led to maremycin A (4) and maremycin D, (8). High optical purity of 4 was confirmed by chiral HPLC comparison with ent-4 prepared from ent-15 and 13.

  DOI：

  10.3987/com-14-s(k)93
• 作为产物：
  描述：

  1-甲基靛红 在 氢氧化钾 、 硫酸 作用下， 以 乙醇 为溶剂， 生成 (3E)-3-ethylidene-1-methyl-1,3-dihydro-2H-indol-2-one
  参考文献：
  名称：

  New Diastereoselective Synthesis of 3-Alkylidene-1-methyloxindoles

  摘要：

  在碱性介质中，将烷基或芳基取代的α-取代乙酰苯加入到N-甲基亚苄基中，可得到相应α-取代的3-苯甲酰甲基-3-羟基-1-甲基吲哚的非对映异构体混合物，产率良好。在无水条件下（0°C时的浓硫酸），这些加合物消除苯甲酸而非水，以定量产率得到纯的（E）-3-亚烷基衍生物。对α-未取代的类似物施以相同处理，脱水反应得到纯的（Z）-3-苯甲酰亚甲基-1-甲基吲哚。

  DOI：

  10.1055/s-2002-19299
• 作为试剂：
  描述：

  (2'R,3S,3a'S,7'S)-1,2'-dimethyl-7'-phenyl-6',7'-dihydrospiro[indole-3,3'-isoxazolo[3,2-c][1,4]oxazine]-2,4'(1H,3a'H)-dione 在 (3E)-3-ethylidene-1-methyl-1,3-dihydro-2H-indol-2-one 、 palladium hydroxide, 20 wt% on carbon 、 氢气 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 、 甲苯 、 苯 为溶剂， 反应 38.5h， 生成
  参考文献：
  名称：

  Total Synthesis of Maremycins A and D1 Using Chiral and Cyclic Nitrone with (E)-3-Ethylidene-1-methylindolin-2-one

  摘要：

  Total syntheses of maremycin A (4) and maremycin D, (8) were described, featuring 1,3-dipolar cycloaddition of a chiral cyclic nitrone 15 with (E)-3-ethylidene-1-methylindolin-2-one (13). The cycloaddition was reversible, especially at high temperature in the presence of a Lewis acid or in a solvent possessing a high acceptor number. One of the cycloadducts was efficiently led to maremycin A (4) and maremycin D, (8). High optical purity of 4 was confirmed by chiral HPLC comparison with ent-4 prepared from ent-15 and 13.

  DOI：

  10.3987/com-14-s(k)93

文献信息

• New Diastereoselective Synthesis of 3-Alkylidene-1-methyloxindoles
  作者：Carmen Avendaño、Pilar López-Alvarado

  DOI：10.1055/s-2002-19299

  日期：——

  Addition of alkyl or aryl α-substituted acetophenones to N-methylisatin in basic media gives diastereomeric mixtures of the corresponding α-substituted 3-benzoylmethyl-3-hydroxy-1-methyloxindole in good yields. Under anhydrous conditions (concentrated sulfuric acid at 0 °C) these adducts eliminate benzoic acid, instead of water, to give pure (E)-3-alkylidene derivatives in quantitative yield. Applying the same treatment to the α-unsubstituted analogue, dehydration took place to give pure (Z)-3-benzoylmethylen-1-methyloxindole.

  在碱性介质中，将烷基或芳基取代的α-取代乙酰苯加入到N-甲基亚苄基中，可得到相应α-取代的3-苯甲酰甲基-3-羟基-1-甲基吲哚的非对映异构体混合物，产率良好。在无水条件下（0°C时的浓硫酸），这些加合物消除苯甲酸而非水，以定量产率得到纯的（E）-3-亚烷基衍生物。对α-未取代的类似物施以相同处理，脱水反应得到纯的（Z）-3-苯甲酰亚甲基-1-甲基吲哚。
• Photoinduced cyclizations of mono- and dianions of N-acyl-o-chloroanilines and N-acyl-o-chlorobenzylamines as general methods for the synthesis of oxindoles and 1,4-dihydro-3(2H)-isoquinolinones
  作者：R. Richard Goehring、Yesh P. Sachdeva、Jyothi S. Pisipati、Mark C. Sleevi、James F. Wolfe

  DOI：10.1021/ja00288a027

  日期：1985.1

  L'influence du rayonnement proche UV et l'effet d'inhibiteurs impliquent un mecanisme radicalaire en chaine

  L'influence du rayonnement proche UV et l'effet d'inhibiteurs impliquent un mecanisme crazyaire en chaine
• Copper-catalyzed hydroboration of alkenyl oxindoles
  作者：Maria Eduarda Contreira、Diogo S. Lüdtke、Angélica V. Moro

  DOI：10.1016/j.tetlet.2018.06.009

  日期：2018.7

  Herein we describe the NHC-Cu(I)-catalyzed hydroboration of alkenyl oxindoles. The corresponding boronates were obtained in good yields, under operationally simple and environmentally friendly conditions, using ethanol as the solvent. Our studies revealed that water-based systems were not very effective. Furthermore, the obtained products are amenable to further elaboration and can be useful to the

  在本文中，我们描述了NHC-Cu（I）催化的烯基羟吲哚的硼氢化。使用乙醇作为溶剂，在操作简单和环境友好的条件下，以高收率获得了相应的硼酸盐。我们的研究表明，水基系统不是很有效。此外，所获得的产物适于进一步加工，并且可用于合成具有生物学相关性的更广泛范围的含羟吲哚的分子。
• Telescoped Enolate Arylation/HWE Procedure for the Preparation of 3-Alkenyl-Oxindoles: The First Synthesis of Soulieotine
  作者：Alessia Millemaggi、Alexis Perry、Adrian C. Whitwood、Richard J. K. Taylor

  DOI：10.1002/ejoc.200900294

  日期：2009.6

  A telescoped sequence involving palladium-catalysed intramolecular enolate arylation followed by an in situ HWE olefination has been developed to provide rapid access to 3-alkenyl-oxindoles. This “one-pot” process, which is greatly accelerated by microwave irradiation, proceeds with low loadings of palladium(II) acetate (0.2–1.0 mol-%), and has been used to prepare a range of adducts derived from aromatic

  已经开发了涉及钯催化的分子内烯醇芳基化和原位 HWE 烯化的伸缩序列，以提供对 3-烯基-羟吲哚的快速访问。这种通过微波辐射大大加速的“一锅法”过程以低载量的醋酸钯 (II) (0.2–1.0 mol-%) 进行，并已用于制备一系列衍生自芳族、杂芳族的加合物和脂肪醛以及甲醛。此外，还描述了对甲醛加合物的进一步阐述。该方法的适用性已通过首次合成传统中药的一种成分 Soulieotine 来确定。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Asymmetric Synthesis of 2′-Trifluoromethylated Spiro-pyrrolidine-3,3′-oxindoles<i>via</i>Squaramide-Catalyzed Umpolung and 1,3-Dipolar Cycloaddition
  作者：Jinhuan Su、Zelin Ma、Xiaoyuan Li、Li Lin、Zhiqiang Shen、Peiju Yang、Yuan Li、Hailin Wang、Wenjin Yan、Kairong Wang、Rui Wang

  DOI：10.1002/adsc.201600688

  日期：2016.12.7

  introduction of a trifluoromethyl group into the 2′‐position of spiro‐pyrrolidine‐3,3′‐oxindoles is described. By using 1 mol% of a quinine‐derived squaramide as catalyst, the 2,2,2‐trfluoroethylamine (CF3CH2NH2)‐derived ketimine is transformed initially into a trifluoromethylimine through an umpolung reaction. The subsequent 1,3‐dipolar cycloaddition gives the pharmaceutical important target compounds in excellent

  描述了将三氟甲基引入螺吡咯烷-3,3'-吲哚的2'-位。通过使用1 mol％的奎宁衍生的方酰胺作为催化剂，2,2,2-三氟乙胺（CF 3 CH 2 NH 2）衍生的酮亚胺首先通过化学反应转化为三氟甲基亚胺。随后的1,3-偶极环加成使药物具有重要的目标化合物，并具有优异的收率，对映选择性和非对映选择性。