(R)-3-benzyl-2,3-dihydrobenzo[d]isothiazole 1,1-dioxide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: (R)-3-benzyl-2,3-dihydrobenzo[d]isothiazole 1,1-dioxide
• 英文别名: 3-benzyl-2,3-dihydrobenzo[d]isothiazoline 1,1-dioxide；3-benzyl-1,2-benzisothiazoline-1,1-dioxide；(3R)-3-benzyl-2,3-dihydro-1,2-benzothiazole 1,1-dioxide
• 化学式: C₁₄H₁₃NO₂S
• 分子量: 259.329
• InChiKey: LBERYMRGSDXGLH-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-benzyl-1,2-benzisothiazole-1,1-dioxide 在 Ru(OSO₂CF₃)(CH₃C₆H₄CH(CH₃)2)(NH₂CHC₆H₅CHC₆H₅NSO₂CH₃) 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 25.0 ℃ 、5.05 MPa 条件下， 反应 24.0h， 生成 (R)-3-benzyl-2,3-dihydrobenzo[d]isothiazole 1,1-dioxide
  参考文献：
  名称：

  不含磷的手性阳离子Ru-MsDPEN催化剂对环状N-磺酰亚胺的不对称加氢反应

  摘要：

  不含磷的手性阳离子Ru /二胺络合物是有效的催化剂，可用于一系列环状N-磺酰亚胺的不对称加氢反应，提供具有良好或优异对映选择性（高达94％ee）的手性舒马坦衍生物。

  DOI：

  10.1002/cjoc.201090260

文献信息

• Highly Enantioselective Pd-Catalyzed Asymmetric Hydrogenation of Activated Imines
  作者：You-Qing Wang、Sheng-Mei Lu、Yong-Gui Zhou

  DOI：10.1021/jo0700878

  日期：2007.5.1

  complexes are highly effective catalysts for asymmetric hydrogenation of activated imines in trifluoroethanol. The asymmetric hydrogenation of N-diphenylphosphinyl ketimines 3 with Pd(CF3CO2)/(S)-SegPhos indicated 87−99% ee, and N-tosylimines 5 could gave 88−97% ee with Pd(CF3CO2)/(S)-SynPhos as a catalyst. Cyclic N-sulfonylimines 7 and 11 were hydrogenated to afford the useful chiral sultam derivatives in

  Pd /双膦配合物是用于活化的亚胺在三氟乙醇中不对称氢化的高效催化剂。Pd（CF 3 CO 2）/（S）-SegPhos对N-二苯基亚膦酰基酮亚胺3的不对称氢化表明ee为87-99％，N- tosylimines 5与Pd（CF 3 CO 2）可以得到88-97％ee /（S）-SynPhos作为催化剂。环状N-磺酰亚胺7和11 进行氢化，以79-93％ee的比重得到有用的手性舒马坦衍生物，这是重要的有机合成中间体和农业和医药制剂的结构单元。
• Multiple Dendritic Catalysts for Asymmetric Transfer Hydrogenation
  作者：Ying-Chun Chen、Tong-Fei Wu、Jin-Gen Deng、Hui Liu、Xin Cui、Jin Zhu、Yao-Zhong Jiang、Michael C. K. Choi、Albert S. C. Chan

  DOI：10.1021/jo0257795

  日期：2002.7.1

  and were well-characterized by NMR and MS techniques. Their ruthenium complexes prepared in situ had good solubility in the reaction medium (azeotrope of formic acid and triethylamine) and demonstrated high catalytic activity and enantioselectivity comparable to monomeric catalysts in the asymmetric transfer hydrogenation of ketones and imines. Quantitative yields and for some cases a slightly higher

  基于手性二胺的第一代和第二代多个树枝状配体以收敛的方式合成，并通过NMR和MS技术得到了很好的表征。原位制备的钌配合物在反应介质（甲酸和三乙胺的共沸物）中具有良好的溶解性，在酮和亚胺的不对称转移加氢反应中，与单体催化剂相比具有较高的催化活性和对映选择性。在树突状催化中获得定量产率，并且在某些情况下获得更高的对映选择性（高达98.7％ee）。考虑到外围的高局部催化剂浓度，测试了二酮在表面催化单元之间可能的协同反应性，但未发现明显差异。
• Enantioselective Intramolecular Benzylic CH Bond Amination: Efficient Synthesis of Optically Active Benzosultams
  作者：Masami Ichinose、Hidehiro Suematsu、Yoichi Yasutomi、Yota Nishioka、Tatsuya Uchida、Tsutomu Katsuki

  DOI：10.1002/anie.201101801

  日期：2011.10.10

  'Salen' along: The iridium(III)–salen complex 1 efficiently catalyzes the title reaction of 2‐ethylbenzenesulfonyl azides to give five‐membered sultams with high enantioselectivity. Other 2‐alkyl‐substitued substrates lead to five‐ and six‐membered sultams with high enantioselectivity; the regioselectivity depends upon the substrate and the catalyst used. EDG=electron‐donating group.

  沿'Salen'方向移动：铱（III）-salen配合物1有效催化2-乙基苯磺酰叠氮化物的标题反应，从而产生具有高对映选择性的五元磺胺。其他的被2-烷基取代的底物导致对映体选择性高的五元和六元均聚物。区域选择性取决于所用的底物和催化剂。EDG =给电子基团。
• Synthesis of polymer-immobilized TsDPEN ligand and its application in asymmetric transfer hydrogenation of cyclic sulfonimine
  作者：Haruki Sugie、Yosuke Hashimoto、Naoki Haraguchi、Shinichi Itsuno

  DOI：10.1016/j.jorganchem.2013.09.008

  日期：2014.2

  Crosslinked polymers containing chiral N-sulfonylated diamine (TsDPEN) structure were synthesized by radical polymerization of chiral N1-(4-vinylbenzenesulfonyl)-1,2-diphenylethylene-1,2-diamine, divinylbenzene and achiral vinyl monomer. The polymer-immobilized chiral complex was prepared from the polymeric TsDPEN with ruthenium dichloride p-cymene. Asymmetric transfer hydrogenation of cyclic sulfonimine was performed using the polymer-immobilized TsDPEN-Ru (II) complex. The hydrophobic-hydrophilic balance of the polymers was tuned by means of the incorporation of the achiral vinyl monomers, which strongly influenced on the catalytic activity of the polymeric catalyst. In most cases the amphiphilic polymer-immobilized chiral catalysts are highly active in the asymmetric transfer hydrogenation. Enantioenriched sultam with up to 98% ee was obtained by using polymer-immobilized chiral catalysts containing quaternary ammonium salt in CH2Cl2. Some of the polymer-immobilized chiral catalysts containing quaternary ammonium salt were successfully used in water. Up to 95% ee was obtained by using the polymeric catalyst in water. Most of the quaternized polymeric catalysts showed sufficient reactivity and higher enantioselectivities compared with that of low-molecular-weight catalyst in water. (c) 2013 Elsevier B.V. All rights reserved.
• A Chiral Rhodium Complex for Rapid Asymmetric Transfer Hydrogenation of Imines with High Enantioselectivity
  作者：Jianmin Mao、David C. Baker

  DOI：10.1021/ol990098q

  日期：1999.9.1

  [GRAPHICS]A chiral rhodium complex, (R)-Cp*RhCl[(1S,2S)-p-TsNCH(C6H5)CH(C6H5)NH2] (1a, (S,S)-Cp*RhCITsDPEN), generated from [Cp*RhCl2](2) and (1S,2S) N-p-toluenesulfonyl-1,2-diphenylethylenediamine [(S,S) TsDPEN], and its enantiomer 1b were found to provide superior catalysts for the rapid, high yielding, asymmetric transfer hydrogenation of some heterocyclic imines, using an HCO2H-Et3N azeotrope as the hydrogen source.