3-allyl-1-benzyl-3-(hydroxymethyl)indolin-2-one | 1229648-97-8

• 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: 3-allyl-1-benzyl-3-(hydroxymethyl)indolin-2-one
• 英文别名: 1-Benzyl-3-(hydroxymethyl)-3-prop-2-enylindol-2-one；1-benzyl-3-(hydroxymethyl)-3-prop-2-enylindol-2-one
• CAS: 1229648-97-8
• 化学式: C₁₉H₁₉NO₂
• 分子量: 293.365
• InChiKey: CKRQTOAODCEXSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 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：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-allyl-1-benzyl-3-(hydroxymethyl)indolin-2-one 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 、 水 为溶剂， 以41%的产率得到1-benzyl-3-(2,3-dihydroxypropyl)-3-(hydroxymethyl)-2-oxo-2,3-dihydroindole
  参考文献：
  名称：

  Applications of NHC-mediated O- to C-carboxyl transfer: synthesis of (±)-N-benzyl-coerulescine and (±)-horsfiline

  摘要：

  NHC-promoted O- to C-carboxyl transfer of 3-allyl indolyl phenyl carbonates generates 3-allyl-3-phenoxycarbonyl-oxindoles with good catalytic efficiency, which are readily converted into (+/-)-N-benzylcoerulescine and (+/-)-horsfiline. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.047
• 作为产物：
  描述：

  phenyl 3-allyl-1-benzyl-2-oxo-2,3-dihydroindole carboxylate 在 sodium tetrahydroborate 、 calcium chloride 作用下， 以 甲醇 为溶剂， 以80%的产率得到3-allyl-1-benzyl-3-(hydroxymethyl)indolin-2-one
  参考文献：
  名称：

  Applications of NHC-mediated O- to C-carboxyl transfer: synthesis of (±)-N-benzyl-coerulescine and (±)-horsfiline

  摘要：

  NHC-promoted O- to C-carboxyl transfer of 3-allyl indolyl phenyl carbonates generates 3-allyl-3-phenoxycarbonyl-oxindoles with good catalytic efficiency, which are readily converted into (+/-)-N-benzylcoerulescine and (+/-)-horsfiline. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.047

文献信息

• <i>Candida antarctica</i> lipase‐B‐catalyzed kinetic resolution of 1,3‐dialkyl‐3‐hydroxymethyl oxindoles
  作者：Naveen Kumar、Akshay Kumar、Subash Chandra Sahoo、Swapandeep Singh Chimni

  DOI：10.1002/chir.23284

  日期：2020.12

  of 1,3‐dialkyl‐3‐hydroxymethyl oxindoles has been performed to obtain (R)‐1,3‐dialkyl‐3‐acetoxymethyl oxindoles with up to 99% ee and (S)‐1,3‐dialkyl‐3‐hydroxymethyl oxindoles with up to 78% ee using vinyl acetate as acylating agent and acetonitrile as solvent transforming (S)‐3‐allyl‐3‐hydroxymethyl oxindole to (3S)‐1′‐benzyl‐5‐(iodomethyl)‐4,5‐dihydro‐2H‐spiro[furan‐3,3′‐indolin]‐2′‐one. The optically

  南极念珠菌(CAL-B) 脂肪酶催化拆分 1,3-二烷基-3-羟甲基羟甲基羟吲哚，获得 ( R )-1,3-二烷基-3-乙酰氧基甲基羟吲哚，其ee和 ( S )-1,3-二烷基-3-羟甲基羟甲基羟吲哚，具有高达 78% ee使用乙酸乙烯酯作为酰化剂和乙腈作为溶剂将 ( S )-3-烯丙基-3-羟甲基羟甲基羟吲哚转化为 ( 3S )-1'- benzyl-5-(iodomethyl)-4,5-dihydro-2 H - spiro[furan-3,3'-indolin]-2'-one。光学活性的 3-取代-3-羟甲基羟吲哚和螺-羟吲哚是合成潜在生物活性分子的关键合成子。
• Unified Approach to Fused and Spirocyclic Oxindoles through Lewis-Acid-Promoted Opening of Spiroepoxyoxindoles with Allylsilanes: Application to the Formal Synthesis of (±)-Physovenine
  作者：Brijesh M. Sharma、Mahesh Yadav、Rajesh G. Gonnade、Pradeep Kumar

  DOI：10.1002/ejoc.201700259

  日期：2017.5.10

  A method for the C‐3 functionalization of 2‐oxindoles through the Lewis‐acid‐promoted opening of spiroepoxyoxindoles with allylsilanes to give Hosomi–Sakurai‐type products as well as spirocyclic oxindoles with all‐carbon quaternary centres has been developed. A formal synthesis of (±)‐physovenine was accomplished in five steps using this approach.

  已开发出一种方法，该方法通过路易斯酸促进的烯丙基硅烷螺环氧基氧吲哚的路易斯酸促进的开环反应，生成Hosomi-Sakurai型产物以及具有全碳四元中心的螺环氧吲哚，从而对2-氧吲哚进行C-3官能化。使用这种方法，可以在五个步骤中完成（±）-植物蛇毒的正式合成。
• Reversal of Selectivity in C3-Allylation and Formal [3 + 2]-Cycloaddition of Spiro-epoxyoxindole: Unified Synthesis of Spiro-furanooxindole, (±)-<i>N</i>-Methylcoerulescine, (±)-Physovenine, and 3a-Allylhexahydropyrrolo[2,3-<i>b</i>]indole
  作者：Saumen Hajra、Sayan Roy、Subrata Maity

  DOI：10.1021/acs.orglett.7b00420

  日期：2017.4.21

  a formal [3 + 2]-annulation reaction of spiro-epoxyoxindoles have been developed and can be accessed simply by changing the reaction conditions. This method has been successfully employed for the synthesis of spiro(pyrrolidinyloxindole), 3a-allylhexahydropyrrolo[2,3-b]indole, and furanoindoline.

  已经开发出有效的路易斯酸催化的区域选择性C 3-烯丙基化和螺-环氧氧吲哚的正式[3 + 2]-环化反应，并且可以通过改变反应条件来简单地获得。该方法已成功地用于合成螺（吡咯烷基二氧杂吲哚），3a-烯丙基六氢吡咯并[2，3- b ]吲哚和呋喃二氢吲哚。
• Applications of NHC-mediated O- to C-carboxyl transfer: synthesis of (±)-N-benzyl-coerulescine and (±)-horsfiline
  作者：Jennifer E. Thomson、Andrew F. Kyle、Kenneth B. Ling、Siobhan R. Smith、Alexandra M.Z. Slawin、Andrew D. Smith

  DOI：10.1016/j.tet.2010.03.047

  日期：2010.5

  NHC-promoted O- to C-carboxyl transfer of 3-allyl indolyl phenyl carbonates generates 3-allyl-3-phenoxycarbonyl-oxindoles with good catalytic efficiency, which are readily converted into (+/-)-N-benzylcoerulescine and (+/-)-horsfiline. (C) 2010 Elsevier Ltd. All rights reserved.