(S,S)-octane-3,6-diol cyclic sulfate | 136705-67-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫酸及其衍生物
• 英文名称: (S,S)-octane-3,6-diol cyclic sulfate
• 英文别名: (3S,6S)-octanediol cyclic sulfate；(3S,6S)-octane-3,6-diol sulfate；(3S,6S)-3,6-octanediol cyclic sulfate；(4S,7S)-4,7-Diethyl-1,3,2-dioxathiepane 2,2-dioxide
• CAS: 136705-67-4
• 化学式: C₈H₁₆O₄S
• 分子量: 208.279
• InChiKey: RIHQVQJKBHQPNE-YUMQZZPRSA-N

物化性质

• 沸点：
  292.3±7.0 °C(Predicted)
• 密度：
  1.107±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S,S)-octane-3,6-diol cyclic sulfate 在 正丁基锂 、 sodium hydride 作用下， 反应 113.5h， 生成 [2-[[(2R,5R)-2,5-diethylpyrrolidin-1-yl]methyl]phenyl]-diphenylphosphane
  参考文献：
  名称：

  The preparation of trans-2,5-dialkylpyrrolidinylbenzyldiphenylphosphines: new phosphinamine ligands for asymmetric catalysis

  摘要：

  The preparation of new phosphinamine ligands 3a, 3b, possessing an enantiopure trans-2,5-dialkylpyrrolidinyl unit is described. Of the three synthetic approaches investigated, two proved successful with similar overall yields of 50-60%. One approach forms the trans-2,5-dialkylpyrrolidine unit first and then the diphenylphosphine is introduced whilst the other reverses the order of introduction. In each approach the key step is the cyclocondensation of an amine with an enantiopure, dialkyl-substituted 1,4-diol cyclic sulfate. An X-ray crystal structure of the palladium dichloride complex 13 of ligand 3a is presented. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00393-0
• 作为产物：
  描述：

  (3S,6S)-3,6-辛二醇 在 ruthenium trichloride 、 sodium periodate 、 氯化亚砜 作用下， 生成 (S,S)-octane-3,6-diol cyclic sulfate
  参考文献：
  名称：

  Burk, Mark J.; Feaster, John E.; Nugent, William A., Journal of the American Chemical Society, 1993, vol. 115, # 22, p. 10125 - 10138

  摘要：

  DOI：

文献信息

• A Highly Tunable Family of Chiral Bisphospholanes for Rh-Catalyzed Enantioselective Hydrogenation Reactions
  作者：Jens Holz、Odalys Zayas、Haijun Jiao、Wolfgang Baumann、Anke Spannenberg、Axel Monsees、Thomas H. Riermeier、Juan Almena、Renat Kadyrov、Armin Börner

  DOI：10.1002/chem.200600033

  日期：2006.6.23

  enantioselectivities in methanol as the solvent. This may account for optimised steric and electronic effects. However, by changing the solvent catalysts with other backbones can give rise to excellent results. This gives proof that simple correlations between steric and electronic properties and results in the enantioselective hydrogenation frequently claimed in literature are not general.

  通过使用高度灵活和收敛的方法，已经制备了一组16种新的且密切相关的双膦环烷配体。每种合成可以在工业上相关的规模上进行。双膦在连接两个膦酸酯单元的桥的性质上不同。桥由三元，四元，五元和六元杂环或脂环族环形成。通过使用理论计算（DFT）和分析测量结果（（31）P和（103）Rh NMR光谱，X射线结构分析）研究了双膦酮及其Rh预催化剂。研究表明，基于具有马来酸酐或马来酰亚胺桥的配体的催化剂在甲醇作为溶剂中具有不断优异的对映选择性。这可以说明优化的空间和电子效果。然而，通过改变溶剂催化剂与其他主链可以产生优异的结果。这证明了在空间性质和电子性质之间的简单关联以及导致文献中经常要求的对映选择性氢化的结果并不普遍。
• [DE] FERROCENYL-1, 2-DIPHOSPHINE, DEREN HERSTELLUNG UND DEREN VERWENDUNG<br/>[EN] FERROCENYL-1, 2-DIPHOSPHINES, THE PRODUCTION THEREOF AND THEIR USE<br/>[FR] FERROCENYL-1, 2-DIPHOSPHINES, LEUR PREPARATION ET LEUR UTILISATION
  申请人：SOLVIAS AG

  公开号：WO2005056568A1

  公开（公告）日：2005-06-23

  Verbindungen der Formel (I) in Form von Racematen, Gemischen von Diastereomeren oder im wesentlichen reinen Diastereomeren, worin R1 ein Wasserstoffatom oder C1-C4-Alkyl bedeutet, und wenigstens ein Sekundärphosphin eine unsubstituierte oder substituierte zyklische Phosphingruppe darstellt, oder deren Phosphoniumsalze mit ein oder zwei monovalenten Anionen oder einem divalenten Anion. Die Verbindungen der Formel (I) werden über ein neues Verfahren zugänglich und sind wertvolle Liganden für katalytisch wirksame Metallkomplexe in der asymmetrischen Synthese.

  Formula (I)的连接形式，以拉克米形式、二对异构体混合物或基本纯的二对异构体形式存在，其中R1代表氢原子或C1-C4烷基，至少一种次磷酸酯是未取代或取代的环状磷基，或其磷酸铵盐具有一个或两个一价阴离子或一个二价阴离子。Formula (I)的化合物通过一种新方法可获得，并且它们是用于不对称合成中的具有催化活性的金属配合物的宝贵配体。
• trans-2,5-Dialkylpyrrolidinyl-containing phosphinamines. Synthetic and mechanistic studies in Pd-catalysed asymmetric allylic alkylation
  作者：John P. Cahill、Deirdre Cunneen、Patrick J. Guiry

  DOI：10.1016/s0957-4166(99)00418-8

  日期：1999.10

  The preparation of new phosphinamine ligands possessing an enantiopure trans-2,5-dialkylpyrrolidinyl unit linked by a rigid o-phenylene bridge to a diphenylphosphine is described. Only that route forming the trans-2,5-dialkylpyrrolidine in the final step from (2-aminophenyl)diphenylphosphine proved successful. The cyclocondensation proceeded in 48% and 27% yields, respectively, for the dimethyl- and diethyl-analogues. Their palladium complexes were prepared and applied to the test of enantioselective alkylation of 1,3-diphenyl-2-propenyl acetate with dimethyl malonate in high chemical yields but with moderate enantioselectivities of up to 34% ee.H-1 NMR spectra of the eta(3)-allyl Pd complexes of four trans-2,5-dialkylpyrrolidine-containing ligands were analysed in an attempt to explain the results obtained. In the cases of the 1,3-diphenylallyl complexes, two diastereomers were observed for all four ligands and their configurations were assigned with the aid of COSY and NOESY experiments. The catalytic results obtained are best interpreted by the reaction proceeding with nucleophilic attack on the allyl trans to the phosphorus donor atom of the major diastereomer. (C) 1999 Elsevier Science Ltd. All rights reserved.
• [DE] NEUES VERFAHREN ZUR HERSTELLUNG VON ORGANISCHEN PHOSPHORVERBINDUNGEN, MIT DIESEM VERFAHREN HERGESTELLTE PHOSPHORVERBINDUNGEN, DEREN METALLKOMPLEXE UND VERWENDUNG<br/>[EN] NOVEL METHOD FOR PRODUCING ORGANIC PHOSPHORUS COMPOUNDS, PHOSPHORUS COMPOUNDS PRODUCED USING SAID METHOD, THE METAL COMPLEXES OF SAID COMPOUNDS, AND USE OF SAME<br/>[FR] NOUVEAU PROCÉDÉ DE PRODUCTION DE COMPOSÉS PHOSPHORÉS ORGANIQUES, COMPOSÉS PHOSPHORÉS AINSI OBTENUS, LEURS COMPLEXES MÉTALLIQUES ET LEUR UTILISATION
  申请人：RWTH AACHEN

  公开号：WO2008055963A1

  公开（公告）日：2008-05-15

  [EN] The invention relates to a method for producing organic phosphorus compounds, to organic phosphorus compounds produced using said method, to novel ligand systems containing trivalent and pentavalent phosphorus, to the metal complexes of said compounds, and to the use of the organic phosphorus compounds or ligand systems and metal complexes.
  [FR] L'invention concerne un procédé de production de composés phophorés organiques, comprenant des composés phosphorés organiques obtenus selon ce procédé, nouveaux systèmes ligands avec un phosphore trivalent et pentavalent, leurs complexes métalliques ainsi que l'utilisation des composés phosphorés organiques ou systèmes ligands et complexes métalliques.
  [DE] Die Erfindung betrifft ein Verfahren zur Herstellung von organischen Phophorverbindungen, mit diesem Verfahren hergestellte organische Phosphorverbindungen, neuen Ligandensystem mit dreiwertigem und fünfwertigem Phosphor, deren Metallkomplexe sowie die Verwendung der organischen Phosphorverbindungen bzw. Ligandensysteme und Metallkomplexe.
• Burk, Mark J.; Feaster, John E.; Nugent, William A., Journal of the American Chemical Society, 1993, vol. 115, # 22, p. 10125 - 10138
  作者：Burk, Mark J.、Feaster, John E.、Nugent, William A.、Harlow, Richard L.

  DOI：——

  日期：——