(1-苄基-3-羟基-2-氧代-2,3-二氢-1H-吲哚-3-基)-乙酸 | 13672-23-6

• 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-苄基-3-羟基-2-氧代-2,3-二氢-1H-吲哚-3-基)-乙酸
• 英文名称: 2-(1-benzyl-3-hydroxy-2-oxoindolin-3-yl)acetic acid
• 英文别名: (1-benzyl-3-hydroxy-2-oxo-2,3-dihydro-indol-3-yl)-acetic acid；<1-Benzyldioxindolyl-(3)>-essigsaeure；(1-Benzyl-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)-acetic acid；2-(1-benzyl-3-hydroxy-2-oxoindol-3-yl)acetic acid
• CAS: 13672-23-6
• 化学式: C₁₇H₁₅NO₄
• mdl: MFCD03043405
• 分子量: 297.31
• InChiKey: LKEBDCHEEHJJIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.176
• 拓扑面积：
  77.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933790090
• 危险类别：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  (1-苄基-3-羟基-2-氧代-2,3-二氢-1H-吲哚-3-基)-乙酸 在 氯化亚砜 、 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 生成 1-benzyl tryptophol
  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：

  1-benzyl-3-hydroxy-3-((3-methyl-4-nitroisoxazol-5-yl)methyl)indolin-2-one 在 potassium permanganate 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以90%的产率得到(1-苄基-3-羟基-2-氧代-2,3-二氢-1H-吲哚-3-基)-乙酸
  参考文献：
  名称：

  3-Hydroxy-3-（（3-3--4-nitroisoxazol-5-yl）methyl）indolin-2-one作为通用中间体，可在水性介质中进行Henry和Friedel-Crafts烷基化反应†

  摘要：

  复古亨利型反应的第一示例是使用报道3-羟基-3 - （（3-甲基-4- nitroisoxazol -5-基）甲基），其制备二氢吲哚-2-酮通过的不含催化剂的亨利反应3,5-二甲基-4-硝基异恶唑和靛红。这些化合物用于通过逆亨利型反应，然后在水中进行Friedel-Crafts烷基化反应（一锅法）选择性合成3-羟基-吲哚基-2-氧吲哚和双吲哚基-2-氧吲哚（对称/不对称）。方法）。3-羟基-3-（（3-甲基-4-硝基异恶唑-5-基）甲基）吲哚-2-酮在水解后生成2-（3-羟基-2-氧代吲哚-3-基）乙酸，为天然产物和生物活性化合物的来源。

  DOI：

  10.1039/c9nj03209f

文献信息

• Substrate-Controlled Diastereo- and Enantiodivergent Synthesis of Bis-Spirocyclopropyloxindoles from Available Isatin as a Single Starting Material
  作者：Mehdi Eskandari、Khosrow Jadidi、Behrouz Notash

  DOI：10.1021/acs.joc.2c02452

  日期：2023.5.5

  The first diastereo- and enantiodivergent asymmetric synthesis of new bis-spirocyclopropyloxindole scaffolds has been accomplished from the readily available isatin as a single starting material. Four rel-(1R,2R,3R), rel-(1S,2S,3R), rel-(1R,2R,3S), and rel-(1S,2S,3S) configurations of desired products were constructed in excellent enantiopurity via a simple switch in substrates using the chiral auxiliary-controlled

  新型双螺环丙基吲哚支架的第一个非对映体和对映体不对称合成已经从现成的靛红作为单一起始材料完成。四个rel -(1 R ,2 R ,3 R )、rel -(1 S ,2 S ,3 R )、rel-(1 R ,2 R ,3 S ) 和rel -(1 S ,2 S , 3秒) 通过使用手性辅助控制方法在底物中进行简单切换，以出色的对映体纯度构建所需产品的构型。通过 X 射线衍射分析证实了具有三个连续的四级/三级手性中心的环加合物的绝对构型。还介绍了多功能前体 3-chlorooxindoles 的简便合成。
• Regioselective synthesis of enantiopure 1,2- and 1,3-dispirooxindoles along with a DFT study
  作者：Kamal Asmari Bardazard、Naeimeh Shahrestani、Amirhosein Zamani、Mehdi Eskandari、Khosrow Jadidi、Mahshid Hamzehloueian、Behrouz Notash

  DOI：10.1039/d2ob02311c

  日期：——

  the enantiomeric purity of the desired products. The mechanism and differences in the regioselectivity of the 1,3-dipolar cycloaddition reactions between the stable azomethane ylides obtained from ninhydrin, pipecolinic acid, and proline with (E)-2-oxoindolin-3-ylideneacetyl sultam were theoretically studied through DFT calculations at the M06-2X/6-31G(d,p) level in methanol.

  在本研究中，使用不同的氨基酸（哌啶酸、肌氨酸、脯氨酸和羟脯氨酸）合成了具有三个或四个连续和两个季立体异构中心的重要对映纯二螺吲哚 [吲哚里西啶、吡咯里西啶和吡咯烷] 衍生物库（高达 96%）通过区域选择性和非对映选择性（高达 99:1）多组分 1,3-偶极环加成策略。根据结果​​，氨基酸的改变导致区域选择性的变化和不寻常的区域异构体（吡咯里西啶与indolizidine/pyrrolidine) 被用来构建一个新的对映体纯的 1,3-dispirooxindole 骨架。环加成的立体化学结果通过单晶 X 射线衍射分析确定，对映体自歧化 (SDE) 测试证实了所需产品的对映体纯度。通过 DFT 计算从理论上研究了从茚三酮、哌啶酸和脯氨酸获得的稳定偶氮甲烷叶立德与 ( E )-2-氧代吲哚啉-3-亚基乙酰基磺胺的1,3-偶极环加成反应的机理和区域选择性差异甲醇中的 M06-2X/6-31G(d
• Acetylphosphonate as a Surrogate of Acetate or Acetamide in Organocatalyzed Enantioselective Aldol Reactions
  作者：Jie Guang、Qunsheng Guo、John Cong-Gui Zhao

  DOI：10.1021/ol301270w

  日期：2012.6.15

  Highly enantioselective aldol reactions of acetylphosphonates and activated carbonyl compounds was realized with cinchona alkaloid derived catalysts, in which the acetylphosphonate was directly used as an enolate precursor for the first time. The aldol product obtained was converted in situ to its corresponding ester or amide through methanolysis or aminolysis. The overall process may be viewed as formal highly enantioselective acetate or acetamide aldol reactions, which are very difficult to achieve directly with organocatalytic methods.
• A versatile synthetic methodology for the synthesis of tryptophols
  作者：Simon J Garden、Rosângela B da Silva、Angelo C Pinto

  DOI：10.1016/s0040-4020(02)01048-7

  日期：2002.10

  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.
• 3-Hydroxy-3-((3-methyl-4-nitroisoxazol-5-yl)methyl)indolin-2-one as a versatile intermediate for retro-Henry and Friedel–Crafts alkylation reactions in aqueous medium
  作者：Sakkani Nagaraju、Kota Sathish、Banoth Paplal、Neeli Satyanarayana、Dhurke Kashinath

  DOI：10.1039/c9nj03209f

  日期：——

  retro-Henry type reaction is reported using 3-hydroxy-3-((3-methyl-4-nitroisoxazol-5-yl)methyl)indolin-2-ones which are prepared via catalyst-free Henry reaction of 3,5-dimethyl-4-nitroisoxazole and isatin. These compounds were used for the selective synthesis of 3-hydroxy-indolyl-2-oxindoles and bis-indolyl-2-oxindoles (symmetric/unsymmetric) via retro-Henry type reaction followed by Friedel–Crafts alkylation

  复古亨利型反应的第一示例是使用报道3-羟基-3 - （（3-甲基-4- nitroisoxazol -5-基）甲基），其制备二氢吲哚-2-酮通过的不含催化剂的亨利反应3,5-二甲基-4-硝基异恶唑和靛红。这些化合物用于通过逆亨利型反应，然后在水中进行Friedel-Crafts烷基化反应（一锅法）选择性合成3-羟基-吲哚基-2-氧吲哚和双吲哚基-2-氧吲哚（对称/不对称）。方法）。3-羟基-3-（（3-甲基-4-硝基异恶唑-5-基）甲基）吲哚-2-酮在水解后生成2-（3-羟基-2-氧代吲哚-3-基）乙酸，为天然产物和生物活性化合物的来源。