(+)-(R)-6-chlorothiochroman-4-ol | 147592-13-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫铬烷
• 英文名称: (+)-(R)-6-chlorothiochroman-4-ol
• 英文别名: (R)-6-chloro-thiochroman-4-ol；(4R)-6-chloro-3,4-dihydro-2H-thiochromen-4-ol
• CAS: 147592-13-0
• 化学式: C₉H₉ClOS
• 分子量: 200.689
• InChiKey: KGOKMXKVFZSSOE-MRVPVSSYSA-N

物化性质

• 熔点：
  102-104 °C
• 沸点：
  319.0±42.0 °C(Predicted)
• 密度：
  1.387±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 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：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+)-(R)-6-chlorothiochroman-4-ol 、 乙酸酐 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 0.08h， 生成
  参考文献：
  名称：

  Chiral spiroaminoborate ester as a highly enantioselective and efficient catalyst for the borane reduction of furyl, thiophene, chroman, and thiochroman-containing ketones

  摘要：

  Prochiral heteroaryl ketones containing furan, thiophene, chroman, and thiochroman moieties were successfully reduced in the presence of 1-10 mol% of spiroaminoborate ester 1 with different borane sources to afford non-racemic alcohols in up to 99% ee. In addition, modest enantioselectivity, around 80% ee, was achieved in the reduction of linear alpha,beta-unsaturated heteroaryl ketones. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.11.009
• 作为产物：
  描述：

  6-氯硫代苯并二氢吡喃-4-酮 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 水 、 sodium formate 、 (1R,2R)-(-)-N-(对甲基苯磺酰基)-1,2-二苯基乙二胺 作用下， 反应 0.33h， 以95%的产率得到
  参考文献：
  名称：

  使用钌催化剂的酮的机械化学、水辅助不对称转移氢化

  摘要：

  使用原位形成的 Noyori-  Ikariya Ru-配合物和甲酸钠作为球磨机中的氢供体，首次报道了前手性酮的高效水相机械化学不对称转移氢化。

  DOI：

  10.1002/cctc.202101501

文献信息

• Novel dimethoxy(aminoalkoxy)borate derived from (S)-diphenylprolinol as highly efficient catalyst for the enantioselective boron-mediated reduction of prochiral ketones
  作者：Viatcheslav Stepanenko、Margarita Ortiz-Marciales、Charles L. Barnes、Carmelo Garcia

  DOI：10.1016/j.tetlet.2008.12.061

  日期：2009.3

  The novel dimethoxyl(aminoalkoxy)borate 1 was isolated as a white crystalline dimer joined by H-bonding as evidenced by X-ray analysis, and demonstrated to be a highly effective catalyst for the asymmetric reduction of representative prochiral ketones with borane–DMS. Optically pure alcohols were obtained using only 1 mol % of catalyst 1 in up to 99% ee.

  X 射线分析证明，新型二甲氧基（氨基烷氧基）硼酸酯1为白色结晶二聚体，通过氢键连接，并被证明是硼烷-DMS 不对称还原代表性前手性酮的高效催化剂。仅使用 1 mol% 的催化剂1，在高达 99% ee 的情况下即可获得光学纯醇。
• (η⁶-Arene)Ru^II/Chiral SN Ligand: A Novel Bifunctional Catalyst System for Asymmetric Transfer Hydrogenation of Aromatic Ketones
  作者：Takao Ikariya、Masato Ito、Yuji Shibata、Akira Watanabe

  DOI：10.1055/s-0029-1217349

  日期：——

  A binary catalyst system of [RuCl2(η6-arene)]2 and a protic aminothiol (SN) ligand has been found to promote hydrogen transfer between alcohols and carbonyl compounds. The chiral catalyst system with the pipecolinol-derived chiral SN ligand displays excellent stereoselectivity in the asymmetric transfer hydrogenation of aromatic ketones using HCO2H-Et3N. Novel unsymmetrical bis(thiolate)-bridged binuclear complex, which is relevant to the generation of catalytically active species, has been synthesized and structurally characterized.

  发现了一种二元催化剂体系，由 [RuCl2(η6-芳烃)]2 和质子性氨基硫醇 (SN) 配体组成，能够促进醇和羰基化合物之间的氢转移。使用 HCO2H-Et3N 的具有哌啶醇衍生的手性 SN 配体的二元催化剂体系在对芳香酮的不对称转移氢化中显示出优异的立体选择性。合成并结构表征了一种新型非对称双硫醇盐桥连的双核配合物，该配合物与催化活性物种的生成相关。
• Synthesis of Spiroborate Esters from 1,2-Aminoalcohols, Ethylene Glycol and Triisopropyl Borate: Preparation of (<i>S</i>)-1-(1,3,2-Dioxaborolan-2-yloxy)-3-Methyl-1,1-Diphenylbutan-2-Amine
  作者：Viatcheslav Stepanenko、Kun Huang、Margarita Ortiz-Marciales

  DOI：10.1002/0471264229.os087.04

  日期：2010.12.17
• Mechanochemical, Water‐Assisted Asymmetric Transfer Hydrogenation of Ketones Using Ruthenium Catalyst
  作者：Vanessza Judit Kolcsár、György Szőllősi

  DOI：10.1002/cctc.202101501

  日期：2022.2.8

  The first highly efficient, aqueous phase mechanochemical asymmetric transfer hydrogenation of prochiral ketones is reported using in situ formed Noyori-Ikariya Ru-complex and sodium formate as hydrogen donor in ball mill.

  使用原位形成的 Noyori-  Ikariya Ru-配合物和甲酸钠作为球磨机中的氢供体，首次报道了前手性酮的高效水相机械化学不对称转移氢化。
• Chiral spiroaminoborate ester as a highly enantioselective and efficient catalyst for the borane reduction of furyl, thiophene, chroman, and thiochroman-containing ketones
  作者：Viatcheslav Stepanenko、Melvin De Jesús、Wildeliz Correa、Lorianne Bermúdez、Cindybeth Vázquez、Irisbel Guzmán、Margarita Ortiz-Marciales

  DOI：10.1016/j.tetasy.2009.11.009

  日期：2009.12

  Prochiral heteroaryl ketones containing furan, thiophene, chroman, and thiochroman moieties were successfully reduced in the presence of 1-10 mol% of spiroaminoborate ester 1 with different borane sources to afford non-racemic alcohols in up to 99% ee. In addition, modest enantioselectivity, around 80% ee, was achieved in the reduction of linear alpha,beta-unsaturated heteroaryl ketones. (C) 2009 Elsevier Ltd. All rights reserved.