1,3-二氢-3-羟基-3-(2-氧代丙基)-2H-吲哚-2-酮 | 33417-17-3

• 物质功能分类: 天然产物 - 生物碱
• 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: 1,3-二氢-3-羟基-3-(2-氧代丙基)-2H-吲哚-2-酮
• 英文名称: 3-hydroxy-3-(2-oxopropyl)indolin-2-one
• 英文别名: 3-(2-oxopropyl)-3-hydroxy-indolin-2-one；3-Hydroxy-3-(2-oxopropyl)-1,3-dihydro-2H-indol-2-one；3-hydroxy-3-(2-oxopropyl)-1H-indol-2-one
• CAS: 33417-17-3
• 化学式: C₁₁H₁₁NO₃
• mdl: MFCD00182845
• 分子量: 205.213
• InChiKey: CBMTTXBZZZABGG-UHFFFAOYSA-N

物化性质

• 熔点：
  167-168℃ (Decomposition)
• 沸点：
  450.2±45.0 °C(Predicted)
• 密度：
  1.301±0.06 g/cm3(Predicted)
• 溶解度：
  27.6 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933790090
• 储存条件：
  2-8℃

制备方法与用途

3-丙酮基-3-羟基辛醇（AHO）是一种有效的植物系统获得性抗性（SAR）诱导剂，能够增强烟草植株对烟草花叶病毒（TMV）及真菌病原体环孢丹毒的抵抗力。研究发现，3-乙酰基-3-羟基辛醇可提高发病相关基因1（PR-1）的表达水平、促进水杨酸（SA）的积累以及增强苯丙氨酸解氨酶活性。

反应信息

• 作为反应物：
  描述：

  1,3-二氢-3-羟基-3-(2-氧代丙基)-2H-吲哚-2-酮 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到3-<2-Hydroxy-propyl>-indol
  参考文献：
  名称：

  A versatile synthetic methodology for the synthesis of tryptophols

  摘要：

  Tryptophols have been obtained in high yields by the reduction of 3-substituted-dioxindoles (obtained by the aldol condensation reaction of ketones with isatins or by a modified Knovenagel malonate condensation) using a borane tetrahydrofuran complex. The reported methodology offers distinct advantages over existing methods for the synthesis of these compounds, including consistently greater yields, diastereoselective syntheses and the possibility for the synthesis of a wide range of structurally different tryptophols. The reduction reaction was found to proceed via an intermediate 1,3-diol-oxindole, which was obtained diastereoselectively and, which was subsequently reduced to the corresponding tryptophol. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01048-7
• 作为产物：
  描述：

  3-(2-oxopropyl)-3-tert-butyldimethylsilyl-oxyindolin-2-one 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以50%的产率得到1,3-二氢-3-羟基-3-(2-氧代丙基)-2H-吲哚-2-酮
  参考文献：
  名称：

  Synthesis of 3-hydroxyindolin-2-one alkaloids, (±)-donaxaridine and (±)-convolutamydines A and E, through enolization–Claisen rearrangement of 2-allyloxyindolin-3-ones

  摘要：

  Claisen rearrangement triggered by enolization of 2-allyloxyindolin-3-ones with DBU was performed in order to prepare 3-allyl-3-hydroxyindolin-2-ones. Total synthesis of 3-hydroxyindolin-2-one alkaloids, (+/-)-donaxaridine, as well as (+/-)-convolutamydines A and E , was achieved by transformation of the allyl moiety of 3-allyl-3-hydroxyindolin-2-ones. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.031

文献信息

• Catalytic Enantioselective Fluorination of Oxindoles
  作者：Yoshitaka Hamashima、Toshiaki Suzuki、Hisashi Takano、Yuta Shimura、Mikiko Sodeoka

  DOI：10.1021/ja0513077

  日期：2005.7.1

  developed a highly efficient catalytic enantioselective fluorination of oxindole derivatives. In the presence of a catalytic amount of chiral Pd complex 2 (2.5 mol %), various substrates, including aryl- and alkyl-substituted oxindoles, were fluorinated in a highly enantioselective manner (up to 96% ee). In addition, when R was a hydrogen atom, enantioselective fluorination followed by solvolysis gave

  我们开发了一种高效催化对映选择性氟化的羟吲哚衍生物。在催化量的手性 Pd 配合物 2 (2.5 mol%) 存在下，各种底物，包括芳基和烷基取代的羟吲哚，以高度对映选择性的方式（高达 96% ee）氟化。此外，当 R 是氢原子时，对映选择性氟化然后溶剂分解得到单氟化酯，ee 高达 93%。据我们所知，这是羟吲哚催化对映选择性氟化的第一个例子。
• Synthesis of potential anticonvulsants: Condensation of isatins with acetone and related ketones
  作者：F.D. Popp、R. Parson、B.E. Donigan

  DOI：10.1002/jps.2600691035

  日期：1980.10

  Substituted isatins were condensed with acetone and other ketones to give analogs of 3-hydroxy-3-acetonyloxindole. Some of these alcohols were dehydrated. Several compounds with anticonvulsant activity were obtained.

  将取代的靛红与丙酮和其他酮缩合，得到3-羟基-3-丙酮酰新吲哚的类似物。这些醇中有些是脱水的。获得了几种具有抗惊厥活性的化合物。
• Synthesis of functionalized 2-oxindoles by Friedel–Crafts reactions
  作者：Makafui Gasonoo、Douglas A. Klumpp

  DOI：10.1016/j.tetlet.2015.06.028

  日期：2015.8

  The product aryl-substituted 2-oxindoles are formed in generally good yields. With substituted arenes such as toluene, bromobenzene, or anisole, the Friedel–Crafts reactions occur with excellent regioselectivity. A mechanism is proposed involving carbocationic electrophiles leading to the aromatic substitution chemistry.

  已经制备了一系列丙酮基取代的3-羟基-2-氧吲哚，并与芳烃在超酸促进的Friedel-Crafts反应中反应。产物芳基取代的2-氧吲哚通常以良好的产率形成。对于取代的芳烃，例如甲苯，溴苯或苯甲醚，Friedel-Crafts反应的区域选择性极好。提出了涉及碳阳离子亲电试剂导致芳族取代化学的机理。
• Kinetic Resolution of Tertiary Alcohols by Chiral DMAP Derivatives: Enantioselective Access to 3-Hydroxy-3-substituted 2-Oxindoles
  作者：Hiroki Mandai、Ryuhei Shiomoto、Kazuki Fujii、Koichi Mitsudo、Seiji Suga

  DOI：10.1021/acs.orglett.0c03956

  日期：2021.2.19

  We developed an efficient acylative kinetic resolution of 3-hydroxy-3-substituted 2-oxindoles by a chiral DMAP derivative having a 1,1′-binaphthyl with two tert-alcohols units. A wide range of 3-hydroxy-3-substituted oxindoles having various functional groups were efficiently resolved (14 examples, up to s = 60) in the presence of 1 mol % of catalyst within 3–9 h. Multigram-scale reactions (10 g) also

  我们通过具有1，1'-联萘基和两个叔醇单元的手性DMAP衍生物开发了3-羟基-3-取代的2-氧吲哚的有效酰基动力学拆分。在1 mol％的催化剂存在下3到9个小时内，可以有效地拆分各种具有各种官能团的3-羟基-3-取代的羟吲哚（14个实例，最高s = 60）。数克级反应（10 g）也在5 h内以高s因子（s = 43）进行。
• Primary-tertiary diamine-catalyzed Michael addition of ketones to isatylidenemalononitrile derivatives
  作者：Akshay Kumar、Swapandeep Singh Chimni

  DOI：10.3762/bjoc.10.91

  日期：——

  Simple primary-tertiary diamines easily derived from natural primary amino acids were used to catalyze the Michael addition of ketones with isatylidenemalononitrile derivatives. Diamine 1a in combination with D-CSA as an additive provided Michael adducts in high yield (up to 94%) and excellent enantioselectivity (up to 99%). The catalyst 1a was successfully used to catalyze the three-component version

  容易从天然伯氨基酸衍生的简单伯-叔二胺用于催化酮与异亚丙基丙二腈衍生物的迈克尔加成。二胺 1a 与作为添加剂的 D-CSA 结合提供了高产率（高达 94%）和出色的对映选择性（高达 99%）的迈克尔加合物。催化剂 1a 通过多米诺克诺韦纳格尔-迈克尔序列成功地用于催化三组分反应。通过以高度对映选择性的方式用硼氢化钠还原，迈克尔加合物 4a 转化为螺吲哚 6。