(R)-3-hydroxy-1-(4-methoxybenzyl)-3-(prop-2-ynyl)indolin-2-one | 1019995-88-0

• 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: (R)-3-hydroxy-1-(4-methoxybenzyl)-3-(prop-2-ynyl)indolin-2-one
• 英文别名: 3-hydroxy-1-(4-methoxybenzyl)-3-(prop-2-yn-1-yl)-1,3-dihydroindol-2-one
• CAS: 1019995-88-0
• 化学式: C₁₉H₁₇NO₃
• 分子量: 307.349
• InChiKey: PWNNLQSKXCVNPW-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  49.77
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  1-[(4-methoxyphenyl)methyl]-3-prop-2-ynyl-3H-indol-2-one 在 氢氧化钾 、 N-(9-anthracenylmethyl)cinchonidinium chloride 、 水 、 氧气 、 亚磷酸三乙酯 、 盐酸 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以92%的产率得到(R)-3-hydroxy-1-(4-methoxybenzyl)-3-(prop-2-ynyl)indolin-2-one
  参考文献：
  名称：

  Catalytic Asymmetric Hydroxylation of Oxindoles by Molecular Oxygen Using a Phase-Transfer Catalyst

  摘要：

  The highly enantioselective catalytic hydroxylation of 3-substituted oxindoles was achieved by using a phase-transfer catalyst with molecular oxygen as an oxidant. The product then was converted to an optically active compound 8, which was a synthetic precursor of alkaloid CPC-1.

  DOI：

  10.1021/ol800260r

文献信息

• Pentanidium catalyzed enantioselective hydroperoxidation of 2-oxindole using molecular oxygen
  作者：Shun Zhou、Lin Zhang、Chun Li、Yuanhu Mao、Jianta Wang、Ping Zhao、Lei Tang、Yuanyong Yang

  DOI：10.1016/j.catcom.2016.04.016

  日期：2016.7

  Pentanidium catalyzed enantioselective 3-hydroperoxidation of 2-oxindoles with molecular oxygen has been established. Various 3-hydroperoxy-2-oxindoles were achieved in good ee and yield.

  已建立了戊氧鎓催化2-氧吲哚与分子氧的对映选择性3-氢过氧化反应。以良好的ee和收率获得了各种3-氢过氧-2-氧吲哚。
• Pentanidium–Catalyzed Enantioselective α-Hydroxylation of Oxindoles Using Molecular Oxygen
  作者：Yuanyong Yang、Farhana Moinodeen、Willy Chin、Ting Ma、Zhiyong Jiang、Choon-Hong Tan

  DOI：10.1021/ol302030v

  日期：2012.9.21

  Pentanidium-catalyzed alpha-hydroxylation of 3-substituted-2-oxindoles using molecular oxygen has been developed with good yields and enantioselectivities. This reaction does not require an additional reductant such as triethyl phosphite, which was typically added to reduce the peroxide intermediate. The reaction was demonstrated to consist of two-steps: an enantioselective formation of hydroperoxide oxindole and a kinetic resolution of the hydroperoxicle oxindole via reduction with enolates generated from the oxindoles.