meso-1,2-bis(1-hydroxypropyl)benzene | 85157-57-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: meso-1,2-bis(1-hydroxypropyl)benzene
• 英文别名: 1,2-bis(1-hydroxypropyl)benzene；(R,S)-1-[2-(1-hydroxy-propyl)-phenyl]-propan-1-ol；(1R)-1-[2-[(1S)-1-hydroxypropyl]phenyl]propan-1-ol
• CAS: 85157-57-9
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: SQAKRQZYQYSWDP-TXEJJXNPSA-N

物化性质

• 沸点：
  318.6±22.0 °C(Predicted)
• 密度：
  1.052±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  苯膦酰二氯 、 meso-1,2-bis(1-hydroxypropyl)benzene 在 吡啶 作用下， 以90.3%的产率得到(1S,5S)-1,5-diethyl-3-phenyl-1,5-dihydro-benzo[e][1,3,2]dioxa-phosphepine-3-oxide
  参考文献：
  名称：

  [EN] CHIRAL DIOLS, THEIR MANUFACTURE AND LIGANDS AND CATALYSTS DERIVED THEREFROM
  [FR] NOUVEAUX DIOLS CHIRAUX, FABRICATION, LIGANDS ET CATALYSEURS DERIVES DE CES DIOLS

  摘要：

  公开号：

  WO2004031109A3
• 作为产物：
  描述：

  (S)-1-(2-溴苯基)丙烷-1-醇 在 正丁基锂 、 ammonium cerium(IV) nitrate 、 sodium hydride 作用下， 以 乙醚 、 环己烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 48.0h， 生成 meso-1,2-bis(1-hydroxypropyl)benzene
  参考文献：
  名称：

  An Efficient Enantioselective Preparation of (S,S)-1,2-Bis(1-hydroxyalkyl)benzene

  摘要：

  (在催化量的(S)-2-(4-甲基哌嗪-1-基甲基)吲哚啉存在下，通过二烷基锌与(S)-2-[1-(4-甲氧基苄氧基)烷基]苯甲醛（86% ee）的对映选择性加成，得到了(S,S)-1,2-双(1-羟基烷基)苯，ee值大于 99%，具有很高的非对映选择性。

  DOI：

  10.1246/cl.2001.1110

文献信息

• Optical Resolution of <i>C</i>₂-Symmetric Racemic 1,4-Diols with <i>o</i>-Xylylene Structure by Chiral Resolving Agent (<i>S</i>)-ALBO-V
  作者：Masatoshi Asami、Lvling Zhong、Naoki Sekiguchi、Kumiko Yamada、Yuya Hiwatashi、Toshiro Taniguchi、Naoya Hosoda、Suguru Ito

  DOI：10.1246/bcsj.20150066

  日期：2015.7.15

  Optical resolution of C2-symmetric racemic 1,4-diols, 1,2-bis(1-hydroxyalkyl)benzene, was examined using (S)-5-allyl-2-oxabicyclo[3.3.0]octene ((S)-ALBO-V) as chiral resolving agent. Diastereomeric...

  使用 (S)-5-allyl-2-oxabicyclo[3.3.0] 辛烯 ((S)- ALBO-V) 作为手性拆分剂。非对映体...
• Asymmetric synthesis of chiral diols by the catalytic enantioselective dialkylation of tere-, iso-, and phthalaldehydes and by a catalytic enantioselective autoinductive reaction
  作者：Kenso Soai、Yukikazu Inoue、Tomohide Takahashi、Takanori Shibata

  DOI：10.1016/0040-4020(96)00810-1

  日期：1996.10

  Optically pure aromatic diols were synthesized by the highly enantioselective dialkylation of aromatic dialdehydes with dialkylzincs in the presence of a catalytic amount of chiral aminoalcohol 1 or chiral thiophosphoramide alcohol 2 with Ti(O-i-Pr)4. The chiral titanium(IV) alkoxide of 4b, a diisopropylated product of isophthalaldehyde, catalyzed the addition of diisopropylzinc to isophthalaldehyde

  在催化量的手性氨基醇1或手性硫代磷酰胺醇2与Ti（O- i- Pr）4催化下，通过芳族二醛与二烷基锌的高度对映选择性二烷基化反应合成了光学纯的芳族二醇。间苯二醛的二异丙基化产物的4b手性钛（IV）醇盐催化将二异丙基锌加到间苯二甲醛中，通过对映选择性自感应反应（高达44％ee）得到具有相同构型的手性醇锌4b。
• Enantioselective dialkylation of 1,2-phthalicdicarboxaldehyde
  作者：Henk Kleijn、Johann T.B.H Jastrzebski、Jaap Boersma、Gerard van Koten

  DOI：10.1016/s0040-4039(01)00586-x

  日期：2001.6

  procedure is reported for the enantioselective synthesis of C2-symmetric diols derived from 1,2-phthalicdicarboxaldehyde. The first step involves the enantioselective addition of a dialkylzinc compound to one of the aldehyde groups, affording a lactol organozinc derivative. In the second step this lactol derivative is converted to the appropriate diol with the aid of a Grignard reagent and subsequent hydrolysis

  报道了一种新的两步一锅法，该方法用于衍生自1,2-邻苯二甲醛的C 2对称二醇的对映选择性合成。第一步涉及将二烷基锌化合物对映选择性地加成到一个醛基上，得到乳醇有机锌衍生物。在第二步中，借助于格利雅试剂将该乳糖醇衍生物转化为合适的二醇，然后进行水解。该方法还可以合成不对称二醇。
• Chiral diols, their manufacture and ligands and catalysts derived therefrom
  申请人：Berens Ulrich

  公开号：US20060030737A1

  公开（公告）日：2006-02-09

  The present invention relates to a method for the preparation of C 2 -symmetric 1,4-diols of the formula IVA or IVB, wherein ring A, R 1 and R 2 have the meanings given in the specification, that makes use of the metallation of pure enantiomers of α-(aryl or heteroaryl)-α-substituted alkanol compounds or the use of said alkanol compounds in the preparation of said mmetric 1,4-diols; novel C 2 -symmetric 1,4-diols in enantiomerically pure form; and methods of use or their use in the synthesis of chiral ligands which find use to produce catalysts for a variety of asymmetric transformations such as hydrogenations.

  本发明涉及一种制备式IVA或IVB的C2对称1,4-二醇的方法，其中环A、R1和R2具有规范中给出的含义，利用纯对映体α-(芳基或杂环芳基)-α-取代烷醇化合物的金属化或利用该烷醇化合物制备所述对称1,4-二醇；新颖的对映纯形式的C2对称1,4-二醇；以及它们在合成手性配体中的应用或用于制备各种不对称转化的催化剂，例如氢化反应。
• Synthesis of α,β-unsaturated dioxanes, dioxolanes and dioxepanes by trans-acetalisation of dimethylacetals with meso or C2-symmetrical 1,2-, 1,3- and 1,4-diols
  作者：Loı̈c Lemiègre、Fleur Lesetre、Jean-Claude Combret、Jacques Maddaluno

  DOI：10.1016/j.tet.2003.11.009

  日期：2004.1

  Several o-dibenzylic diols were prepared reacting organometallics with o-phthalaldehyde at room temperature in ether. The identity of the meso and C-2-symmetrical (D,L) isomers as well as their ratio were determined by chiral gas chromatography. The meso and C-2 (racemic) stereoisomeric diols were easily separated by flash chromatography on silica gel. A set of 18 alpha,beta-unsaturated acetals were then prepared reacting those, as well as commercially available 1,2, 1,3 and 1,4 diols, with the corresponding methylacetals in acidic medium. A trans-acetalisation procedure adapted to the cases of fragile allylic alcohols or unfavorable 1,6 diols-derived dioxonanes based on a Dean-Stark trapping of methanol was also employed. (C) 2003 Elsevier Ltd. All rights reserved.