2-异丁吲哚丁醇 | 143880-78-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 中文名称: 2-异丁吲哚丁醇
• 中文别名: (R)-(-)-2-(2-异二氢氮杂茚基)丁烷-1-醇
• 英文名称: (R)-(-)-2-(2-iso-indolinyl)butan-1-ol
• 英文别名: (R)-(-)-2-(2-isoindolinyl)butan-1-ol；(R)-2-(isoindolin-2-yl)butan-1-ol；(2R)-2-(1,3-dihydroisoindol-2-yl)butan-1-ol
• CAS: 143880-78-8；135711-18-1
• 化学式: C₁₂H₁₇NO
• 分子量: 191.273
• InChiKey: OGAAQVONYOTBGB-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氨基丁醇 、 间二氯苄 在 sodium carbonate 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以51%的产率得到2-异丁吲哚丁醇
  参考文献：
  名称：

  Determination of the enantiomeric excesses of chiral acids by 19F NMR studies of their esters deriving from (R)-(+)-2-(trifluoromethyl)benzhydrol

  摘要：

  15 Chiral acids were esterified with optically pure (R)-(+)-2-(trifluoromethyl)benzhydrol (R)-(+)-1, a readily available reagent. With respect to the carboxy group, the stereogenic centre is in the beta position in the case of the acids 5a-10a and 12a-16a, and in the alpha position in the case of the acids 17a-20a. The diastereomeric excesses of the corresponding esters 5b-10b and 12b-20b, respectively, were easily determined by means of F-19 NMR. These d.e. values were in very good agreement with the e.e. values of the corresponding acids when the latter were known compounds.

  DOI：

  10.1016/0957-4166(94)80154-1
• 作为试剂：
  描述：

  2-甲基二苯甲酮 在 lithium aluminium tetrahydride 、 2-异丁吲哚丁醇 作用下， 以 乙醚 为溶剂， 反应 0.25h， 以73%的产率得到(R)-o-methylbenzhydrol
  参考文献：
  名称：

  Preparative synthesis of optically pure ortho-substituted benzhydrols by asymmetric reductions of the corresponding benzophenones

  摘要：

  Lithium aluminium hydride previously treated with 2.5 equivalents of (S)-(+) or (R)-(-)-2 -(2-iso-indolinyl)butan-1-ol 3 (readily available reagents) reduced the five ortho-substituted benzophenones 4-6, 8 and 10 into the corresponding optically active benzhydrols with nearly 100% enantiomeric excesses. Other examples of asymmetric reductions of prochiral benzophenones are given.

  DOI：

  10.1016/s0957-4166(00)82179-5

文献信息

• Asymmetric reductions of ketones using lithium aluminium hydride modified with -dialkyl derivatives of (R)-(−)-2-aminobutan-1-ol
  作者：Eric Brown、Annie Penfornis、Joaquim Bayma、Joël Touet

  DOI：10.1016/s0957-4166(00)82113-8

  日期：1991.1

  LiAlH4 previously treated with 2 equivalents of (R)-(−)-2-(2-iso-indolinyl) butan-1-ol (a readily available reagent) reduced 2-chloro and 2,4-dimethyl benzophenones into the corresponding benzhydrols with 100% enantiomeric excess. Other examples of ketone reductions are given.

  预先用2当量的（R）-（-）-2-（2-异吲哚基）丁-1-醇（一种容易获得的试剂）处理过的LiAlH 4将2-氯和2,4-二甲基二苯甲酮还原为相应的对映体过量100％对苯二酚。给出了酮还原的其他实例。
• Synthesis and manufacture of pentostatin and its precursors, analogs and derivatives
  申请人：Phiasivongsa Pasit

  公开号：US20050267056A1

  公开（公告）日：2005-12-01

  Methods and compositions are provided for efficiently preparing and manufacturing pentostatin. Also provided are novel precursors of pentostatin, pentostatin analogs and derivatives. In one aspect of the invention, a method is provided for total chemical synthesis of pentostatin via a route of heterocyclic ring expansion. For example, a heterocyclic pharmaceutical intermediate for drugs such as pentostatin, e.g., the diazepinone precursor, can be obtained efficiently through a ring expansion of an O—C—N functionality in a hypoxanthine or 2′-deoxyinosine derivative. The methods and compositions can also be used to synthesize and manufacture heterocyclic compounds other than pentostatin, especially pharmaceutically important heterocyclic compounds.

  本发明提供了一种高效制备和生产戊糖核苷的方法和组合物。此外，还提供了戊糖核苷的新型前体、戊糖核苷类似物和衍生物。在本发明的一个方面，提供了一种通过杂环环扩展路线对戊糖核苷进行全合成的方法。例如，可以通过对嘌呤嘧啶或2'-去氧肌苷衍生物中的O-C-N官能团进行环扩展，高效地获得用于药物如戊糖核苷的杂环制药中间体，如噻唑环酮前体。这些方法和组合物还可以用于合成和生产除戊糖核苷以外的其他杂环化合物，特别是药物上重要的杂环化合物。
• Synthesis and in vitro antimycobacterial activity of compounds derived from (R)- and (S)-2-amino-1-butanol – The crucial role of the configuration
  作者：Georgi M. Dobrikov、Violeta Valcheva、Margarita Stoilova-Disheva、Georgi Momekov、Pavleta Tzvetkova、Angel Chimov、Vladimir Dimitrov

  DOI：10.1016/j.ejmech.2011.11.035

  日期：2012.2

  The synthesis of 47 structurally diverse compounds incorporating the (R)-2-amino-1-butanol motif has been realized. Ten of these compounds were found to exhibit in vitro specific activity against Mycobacterium tuberculosis H37Rv in a MIC range of 0.65 mu M-14.03 mu M. Five of the most active compounds 11, 22, 23, 31 and 42(5.7-11.1 fold more active than ethambutol) can be outlined with very low cytotoxicity towards human embryonal kidney non-tumour cells (SI ranging from 91.2 to 375.4). For the purpose of comparison the (S)-enantiomers of these most active compounds have been synthesized and evaluated towards M. tuberculosis H(37)Rv showing no activity even at 20-32 fold higher concentrations. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Synthesis of chiral alcohols by asymmetric reductions of various ketones including α-aminophenones
  作者：Eric Brown、Antoine Lézé、Joël Touet

  DOI：10.1016/0957-4166(96)00245-5

  日期：1996.7

  LiAlH4 previously treated with 2.5 equiv. of (S)-(+) or (R)-(-)-2-(2-isoindolinyl)butan-1-ol 1 reduced the six alpha-aminophenones 4-9 into the corresponding optically active beta-aminoalcohols 10-15 whose ee's were in the range 40-97% after chromatography and recrystallization. The asymmetric reduction of the ortho-dimethylaminobenzophenone 18, using the same reducing agents afforded the enantiomerically pure benzhydrols (R)-(-)-19 and (S)-(+)-19, respectively, and in 86-100% yields. The ortho-aminobenzhydrol (S)-(+)-20 and a-fluorenyl ethanol (R)-(+)-23 and (S)-(-)-23 were similarly obtained from the corresponding ketones 17 and 25, respectively. The latter carbinols were obtained in an enantiomerically pure state after recrystallization. Copyright (C) 1996 Elsevier Science Ltd
• SYNTHESIS AND MANUFACTURE OF PENTOSTATIN AND ITS PRECURSORS, ANALOGS AND DERIVATIVES
  申请人：Supergen, Inc.

  公开号：EP1670809A2

  公开（公告）日：2006-06-21