1-benzyl-6,6-dimethyl-6,7-dihydro-1H-indol-4(5H)-one | 66842-60-2

• 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: 1-benzyl-6,6-dimethyl-6,7-dihydro-1H-indol-4(5H)-one
• 英文别名: 1-benzyl-6,6-dimethyl-6,7-dihydro-1H-indole-4(5H)one；1-benzyl-6,7-dihydro-6,6-dimethyl-1H-indol-4(5H)-one；1-Benzyl-6,6-dimethyl-5,7-dihydroindol-4-one
• CAS: 66842-60-2
• 化学式: C₁₇H₁₉NO
• 分子量: 253.344
• InChiKey: DGUUPQGUPSDODK-UHFFFAOYSA-N

物化性质

• 沸点：
  386.5±11.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-benzyl-6,6-dimethyl-6,7-dihydro-1H-indol-4(5H)-one 在 potassium permanganate 、 lipase from Pseudomonas Cepacia 作用下， 以 二甲基亚砜 、 苯 为溶剂， 反应 48.0h， 生成 (S)-1-benzyl-6,7-dihydro-7-hydroxy-6,6-dimethyl-1H-indol-4(5H)-one 、 (R)-1-benzyl-6,7-dihydro-7-hydroxy-6,6-dimethyl-1H-indol-4(5H)-one
  参考文献：
  名称：

  Stereoselective synthesis of optically active 1-benzyl-4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-1H-indol-7-yl acetate and 1-benzyl-6,7-dihydro-7-hydroxy-6,6-dimethyl-1H-indol-4(5H)-one through lipase-catalyzed esterification and transesterification processes

  摘要：

  The enantioselective synthesis of 1-benzyl-4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-1H-indol-7-yl acetate (4) and 1-benzyl-6,7-dihydro-7-hydroxy-6,6-dimethyl-1H-indol-4(5H)-one (5), which are important intermediates in pharmaceutical industry, was carried out for the first time, both by enzyme-mediated hydrolysis and transesterification reactions with high enantiomeric excesses in the presence of various lipases. In either case S enantiomer of (5) was obtained with high enantiomeric excesses at low rate of conversion and E value. However, R enantiomer of (5) was also obtained by transesterification reaction with high optical purity. In the transesterification reaction of (rac-5a) with several lipases in different solvent systems in the peresence of DMAP as an additive and vinyl acetate, E value of the reaction were raised for some enzyme and solvent combination (THF-MJL with >99% ee and E value: 41; for acetonitrile-MJL with 91% ee and E value: 51; for acetonitrile-Amano with 99% ee, E value: 68) showed R-(5) selectivity. Furthermore the conversion value was also increased. The best conversion of the transesterification reaction was 39% with DMSO-HPL showed 73% ee and E value: 15 for R-(5) selectivity and 47% for S-(4) selectivity. The two procedures can therefore be considered as complementary with respect to the final composition. (C) 2014 Published by Elsevier B.V.

  DOI：

  10.1016/j.molcatb.2014.10.015
• 作为产物：
  描述：

  2-重氮基-5,5-二甲基-1,3-环己二酮 在 tris(triphenylphosphine)ruthenium(II) chloride 、 1-butyl-3-methylimidazolium tetrafluoroborate 、 对甲苯磺酸 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 甲苯 为溶剂， 反应 18.33h， 生成 1-benzyl-6,6-dimethyl-6,7-dihydro-1H-indol-4(5H)-one
  参考文献：
  名称：

  钌（II）催化的[3 + 2]环或无环重氮二羰基化合物与烯烃的环加成反应，高效一锅合成多取代的二氢呋喃

  摘要：

  AbstractRuthenium(II)‐phosphine complexes‐catalyzed [3+2] cycloadditions were conducted to synthesize a variety of dihydrofurans by reactions of cyclic or acyclic diazodicarbonyl compounds with olefins. This method represents a direct and efficient one‐pot synthesis for multi‐substituted dihydrofurans under mild reaction conditions with an excellent regioselectivity. Furthermore, to reduce reaction times and increase yields of dihydrofurans, microwave‐assisted tris(triphenylphosphine)ruthenium(II) chloride/ 1‐butyl‐3‐methylimidazolium tetrafluoroborate {Ru(PPh3)3Cl2/[Bmim]BF4}‐catalyzed reactions were also developed. The synthesized dihydrofurans can be readily converted into biologically interesting tetrahydroindoles.magnified image

  DOI：

  10.1002/adsc.201300245

文献信息

• KR2016/20022
  申请人：——

  公开号：——

  公开（公告）日：——
• BOBBITT J. M.; KULKARNI C. L.; DUTTA C. P.; KOFOD H.; CHIONG K. NG., J. ORG. CHEM., 1978, 43, NO 18, 3541-3544
  作者：BOBBITT J. M.、 KULKARNI C. L.、 DUTTA C. P.、 KOFOD H.、 CHIONG K. NG.

  DOI：——

  日期：——