(R)-3-allyl-3-hydroxy-1-(4-methoxybenzyl)indolin-2-one | 1019995-86-8

• 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: (R)-3-allyl-3-hydroxy-1-(4-methoxybenzyl)indolin-2-one
• 英文别名: (3R)-3-hydroxy-1-[(4-methoxyphenyl)methyl]-3-prop-2-enylindol-2-one
• CAS: 1019995-86-8
• 化学式: C₁₉H₁₉NO₃
• 分子量: 309.365
• InChiKey: OYKPTRCNNHJRBE-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-3-allyl-3-hydroxy-1-(4-methoxybenzyl)indolin-2-one 、 乙酸酐 在 吡啶 作用下， 反应 10.0h， 以100%的产率得到3-allyl-1-(4-methoxybenzyl)-2-oxo-2,3-dihydroindol-3-yl acetate
  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
• 作为产物：
  描述：

  1-(4-甲氧基-苄基)-1H-吲哚-2,3-二酮 在 manganese(IV) oxide 、 氟硼酸钠 、 5a(R),10b(S)-5a,10b-dihydro-2-(pentafluorophenyl)-4H,6H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazinium tetrafluoroborate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 magnesium triflate 作用下， 以 四氢呋喃 为溶剂， 反应 55.5h， 生成 (R)-3-allyl-3-hydroxy-1-(4-methoxybenzyl)indolin-2-one
  参考文献：
  名称：

  叔醇的动力学拆分：对3-羟基-3-取代的羟吲哚的高度对映选择性

  摘要：

  对映选择性：3-羟基-3-取代的羟吲哚的第一高度对映选择性的动力学拆分已被N-杂环卡宾（见图）通过氧化酯化催化显影。该方法使用一个简单的程序，并提供出色的对映体纯度的3-羟基-吲哚在3-位带有各种取代基。S＝选择性。

  DOI：

  10.1002/anie.201209043

文献信息

• Bi(OAc)₃/chiral phosphoric acid catalyzed enantioselective allylation of isatins
  作者：Jie Wang、Qingxia Zhang、Yao Li、Xiangshuai Liu、Xin Li、Jin-Pei Cheng

  DOI：10.1039/c9cc07944k

  日期：——

  Herein, we disclosed an efficient protocol for the construction of chiral 3-allyl-3-hydroxyoxindoles via the enantioselective allylation reaction of isatins and allylboronates catalyzed by a simple binary acid Bi(OAc)3/CPA system under mild conditions. The synthetic utility of this strategy has been demonstrated through the formal synthesis of ent-CPC-1.

  在这里，我们公开了一种在温和条件下通过简单的二元酸Bi（OAc）3 / CPA系统催化的靛红和烯丙基硼酸酯的对映选择性烯丙基化反应来构建手性3-烯丙基-3-羟基羟吲哚的有效方案。通过ent-CPC-1的正式合成证明了该策略的综合效用。
• 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。
• Bui, Tommy; Candeias, Nuno R.; Barbas, Carlos F. III, Journal of the American Chemical Society, 2010, vol. 132, p. 5574 - 5575
  作者：Bui, Tommy、Candeias, Nuno R.、Barbas, Carlos F. III

  DOI：——

  日期：——
• 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.
• Kinetic Resolution of Tertiary Alcohols: Highly Enantioselective Access to 3-Hydroxy-3-Substituted Oxindoles
  作者：Shenci Lu、Si Bei Poh、Woon-Yew Siau、Yu Zhao

  DOI：10.1002/anie.201209043

  日期：2013.2.4

  Enantioselective: The first highly enantioselective kinetic resolution of 3‐hydroxy‐3‐substituted oxindoles has been developed through oxidative esterification catalyzed by a N‐heterocyclic carbene (see picture). This method uses a simple procedure and provides 3‐hydroxy‐oxindoles with various substituents at the 3‐position in excellent enantiopurity. S=selectivity.

  对映选择性：3-羟基-3-取代的羟吲哚的第一高度对映选择性的动力学拆分已被N-杂环卡宾（见图）通过氧化酯化催化显影。该方法使用一个简单的程序，并提供出色的对映体纯度的3-羟基-吲哚在3-位带有各种取代基。S＝选择性。