3-hydroxy-1-methyl-3-(1-methyl-2-oxo-2-phenylethyl)-1,3-dihydro-2H-indol-2-one | 98844-05-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-hydroxy-1-methyl-3-(1-methyl-2-oxo-2-phenylethyl)-1,3-dihydro-2H-indol-2-one
• 英文别名: 3-hydroxy-1-methyl-3-(1-methyl-2-oxo-2-phenyl-ethyl)-1,3-dihydro-indol-2-one；1-Methyl-3-hydroxy-2-oxo-3-(1-benzoylethyl)-indolin；3-hydroxy-1-methyl-3-(1-oxo-1-phenylpropan-2-yl)-1,3-dihydro-2H-indol-2-one；3-hydroxy-1-methyl-3-(1-oxo-1-phenylpropan-2-yl)indol-2-one
• CAS: 98844-05-4
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: PIFPNXQKUIQHGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-hydroxy-1-methyl-3-(1-methyl-2-oxo-2-phenylethyl)-1,3-dihydro-2H-indol-2-one 在 硫酸 、 palladium hydroxide, 20 wt% on carbon 、 氢气 作用下， 以 甲醇 、 正己烷 、 甲苯 、 苯 为溶剂， 反应 52.67h， 生成 (3S,6R)-3-{(1R)-1-[(3S)-3-hydroxy-1-methyl-2-oxo-2,3-dihydro-1H-indol-3-yl]ethyl}-6-[(methylsulfanyl)methyl]piperazine-2,5-dione
  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：

  2-吲哚酮 在 四丁基氟化铵 、 sodium hydride 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 18.0h， 生成 3-hydroxy-1-methyl-3-(1-methyl-2-oxo-2-phenylethyl)-1,3-dihydro-2H-indol-2-one
  参考文献：
  名称：

  2-氧辛酮与酮的自氧化/羟醛串联反应：3-羟基-2-氧辛酮合成的绿色方法

  摘要：

  在DMF中存在四丁基氟化铵和分子筛（MS）4Å的情况下，已开发出室温下空气中2-氧吲哚与酮的有效自氧化反应。这种方法可能为多种生物学上重要的3-羟基-3-（2-氧代烷基）-2-氧吲哚提供绿色，实用且不含金属的方案。

  DOI：

  10.1002/chem.201504282

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。
• Autoxidation/Aldol Tandem Reaction of 2-Oxindoles with Ketones: A Green Approach for the Synthesis of 3-Hydroxy-2-Oxindoles
  作者：Qing-Bao Zhang、Wen-Liang Jia、Yong-Liang Ban、Yong Zheng、Qiang Liu、Li-Zhu Wu

  DOI：10.1002/chem.201504282

  日期：2016.2.18

  In the presence of tetrabutylammonium fluoride and molecular sieves (MS) 4 Å in DMF, an efficient autoxidation reaction of 2‐oxindoles with ketones under air at room temperature has been developed. This approach may provide a green, practical, and metal‐free protocol for a wide range of biologically important 3‐hydroxy‐3‐(2‐oxo‐alkyl)‐2‐oxindoles.

  在DMF中存在四丁基氟化铵和分子筛（MS）4Å的情况下，已开发出室温下空气中2-氧吲哚与酮的有效自氧化反应。这种方法可能为多种生物学上重要的3-羟基-3-（2-氧代烷基）-2-氧吲哚提供绿色，实用且不含金属的方案。
• Total Synthesis of Maremycins A and D1 Using Chiral and Cyclic Nitrone with (E)-3-Ethylidene-1-methylindolin-2-one
  作者：Osamu Tamura、Tohru Ueda、Mitsuhide Inada、Nobuyoshi Morita

  DOI：10.3987/com-14-s(k)93

  日期：——

  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.