(1S,2R)-2-bromo-2,3-dihydro-1H-inden-1-ol | 180681-90-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (1S,2R)-2-bromo-2,3-dihydro-1H-inden-1-ol
• CAS: 180681-90-7
• 化学式: C₉H₉BrO
• 分子量: 213.074
• InChiKey: RTESDSDXFLYAKZ-BDAKNGLRSA-N

物化性质

• 沸点：
  318.3±42.0 °C(Predicted)
• 密度：
  1.640±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1S,2R)-2-bromo-2,3-dihydro-1H-inden-1-ol 在 palladium on activated charcoal sodium azide 、 氢气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (1S,2S)-trans-2-amino-1-indanol
  参考文献：
  名称：

  Stereoselective dioxygenase-catalysed benzylic hydroxylation at prochiral methylene groups in the chemoenzymatic synthesis of enantiopure vicinal aminoindanols

  摘要：

  Enantiopure benzylic alcohols containing two stereogenic centres in a cis-relationship result from stereoselective monohydroxylation of achiral 2-substituted indans in cultures of Pseudomonas putida UV4 and are used in the chemoenzymatic synthesis of both cis- and trans-aminoindanol enantiomers. (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00180-2
• 作为产物：
  描述：

  2-茚醇 在 toluene dioxygenase 吡啶 、 三溴化磷 作用下， 以 氯仿 为溶剂， 反应 25.0h， 生成 (1S,2R)-2-bromo-2,3-dihydro-1H-inden-1-ol
  参考文献：
  名称：

  Bowers, Nigel I.; Boyd, Derek R.; Sharma, Narain D., Journal of the Chemical Society. Perkin transactions I, 1999, # 11, p. 1453 - 1461

  摘要：

  DOI：

文献信息

• Comparative study of the vicinal functionalization of olefins with 2:1 bromide/bromate and iodide/iodate reagents
  作者：Manoj K. Agrawal、Subbarayappa Adimurthy、Bishwajit Ganguly、Pushpito K. Ghosh

  DOI：10.1016/j.tet.2009.01.095

  日期：2009.4

  halohydrins, halo methyl ethers, and halo acetates from olefins using 2:1 Br−/BrO3− and I−/IO3− reagents. In many cases both reagents afforded products selectively in high yields. The highest halogen atom efficiencies attained were 97% and 93% for Br−/BrO3− and I−/IO3−, respectively. Of the two reagents, I−/IO3− was established to be the preferred reagent for vicinal functionalization of linear alkenes and

  比较评价在邻位卤代醇，卤代甲基醚和卤代乙酸盐的合成由从使用2-烯烃：1溴- /的BrO 3 -和我- / IO 3 -试剂。在许多情况下，两种试剂都以高收率选择性地提供产物。得到最高卤素原子效率为97％和溴93％- /的BrO 3 -和我- / IO 3 - ，分别。这两个试剂，我- / IO 3 -已确定“丙烯酰胺”是用于直链烯烃的邻位官能化以及用于制备卤代乙酸酯的优选试剂。然而，只有溴- /的BrO 3 -是有效的邻位官能反式-二苯乙烯和查耳酮。
• Method of manufacturing 1-indanone
  申请人：Ichikawa Gosei Chemical Co., Ltd.

  公开号：US06127579A1

  公开（公告）日：2000-10-03

  A method of manufacturing the useful substance 1-indanone from easily obtainable materials consists of reacting an indanyl ether represented by the generic formula ##STR1## under basic conditions to give a novel substance which is the indenyl ether derivative represented by the generic formula ##STR2## and hydrolyzing this to give the 1-indanone represented by the generic formula ##STR3##

  从易获得的材料中制造有用物质1-茚酮的方法包括在碱性条件下反应由通用式##STR1##表示的茚基醚，得到一种新颖物质，即由通用式##STR2##表示的茚基醚衍生物，然后水解这种物质，得到由通用式##STR3##表示的1-茚酮。
• The absolute configuration of 2-bromo-2,3-dihydro-1<i>H</i>-inden-1-ols
  作者：Dmitry V. Prysiazhnuk、Eduard B. Rusanov、Oleg I. Kolodiazhnyi

  DOI：10.1080/00397911.2021.1960378

  日期：2021.10.2

  four possible stereoisomers of cis- and trans-2-bromo-2,3-dihydro-1H-inden-1-ols, which are important intermediates in the synthesis of biologically active compounds, were synthesized and their configurations were studied by enzymatic kinetic resolution with the application of the Kazlauskas rule, X-ray diffraction analysis, as well as NMR using NOE-NMR and Karplus equation. Biocatalytic kinetic trans-esterification

  摘要 顺式和反式 2-bromo-2,3-dihydro-1 H -inden-1-ols 的所有四种可能的立体异构体都被合成，它们是生物活性化合物合成中的重要中间体，并通过酶促研究了它们的构型。通过应用 Kazlauskas 规则、X 射线衍射分析以及使用 NOE-NMR 和 Karplus 方程进行 NMR 的动力学分辨率。生物催化动力学酯交换用于拆分外消旋物。脂肪酶洋葱伯克霍尔德菌和南极念珠菌 B (Novozyme 435) 可有效用作生物催化剂，用于 2-bromo-2,3-dihydro-1 H -inden-1-ols 与乙酸异丙酯的生物催化酯化。2-bromo-2,3-dihydro-1 H的(S,S)-、(R,R)-、(S,R)-和(R,S)-立体异构体的绝对构型-inden-1-ols 成立。
• From simple organobromides or olefins to highly value-added bromohydrins: a versatile performance of dimethyl sulfoxide
  作者：Song Song、Xiaoqiang Huang、Yu-Feng Liang、Conghui Tang、Xinwei Li、Ning Jiao

  DOI：10.1039/c5gc00184f

  日期：——

  A novel and efficient direct transformation of secondary bromides or olefins to highly value-added bromohydrins with DMSO has been disclosed.

  已经公开了用DMSO将仲溴化物或烯烃新颖有效地直接转化成高附加值的溴代醇的方法。
• Convincing Catalytic Performance of Oxo-Tethered Ruthenium Complexes for Asymmetric Transfer Hydrogenation of Cyclic α-Halogenated Ketones through Dynamic Kinetic Resolution
  作者：Taichiro Touge、Hideki Nara、Michio Kida、Kazuhiko Matsumura、Yoshihito Kayaki

  DOI：10.1021/acs.orglett.1c00739

  日期：2021.4.16

  A highly efficient dynamic kinetic resolution of cyclic halohydrins was achieved by the asymmetric transfer hydrogenation of racemic α-haloketones. Bifunctional oxo-tethered Ru(II) catalysts could promote the reduction without deterioration of halogens. By structural tuning of the catalyst, chiral alcohols having halogen, ester, carboxamide, and sulfone functions were obtained variably with excellent

  通过外消旋α-卤代烃的不对称转移氢化，可以实现高效的环卤代醇动力学动力学拆分。双官能的氧束缚Ru（II）催化剂可以促进还原而不会降低卤素的含量。通过催化剂的结构调整，可以可变地获得具有卤素，酯，羧酰胺和砜功能的手性醇，具有出色的非对映异构体和对映体选择性（高达> 99：1 dr和> 99.9 ee），从而提供了一种简捷的合成方法。多巴胺D3受体配体，（+）-PHNO。