(S)-N-(1-(4-methoxyphenyl)ethylidene)-2-methylpropane-2-sulfinamide | 874291-46-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-N-(1-(4-methoxyphenyl)ethylidene)-2-methylpropane-2-sulfinamide
• 英文别名: (S)-(-)-N-[1-(4-methoxyphenyl)ethylidene]-tert-butanesulfinamide
• CAS: 874291-46-0
• 化学式: C₁₃H₁₉NO₂S
• 分子量: 253.365
• InChiKey: QTIRPTNYHRFNHP-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.97
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  38.66
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (S)-N-(1-(4-methoxyphenyl)ethylidene)-2-methylpropane-2-sulfinamide 在 盐酸 、 diMe-Tri-BH3 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 9.17h， 生成 (R)-N-(1-(4-methoxyphenyl)ethyl)benzamide
  参考文献：
  名称：

  N-杂环碳硼烷不对称还原叔丁亚磺酰基酮亚胺

  摘要：

  首次证明了基于三唑核的N-杂环卡宾硼烷（NHC-硼烷）可有效还原多种叔丁烷亚磺酰基酮亚胺。获得了高达95％的产率和高达> 99％的非对映异构体过量。NHC-硼烷表现出优异的活性，与常用的还原剂（如NaBH 4，NaBH 3 CN，1- selectride，Ru催化剂或BH 3 -THF）相比，具有更高的效率或与之相当。

  DOI：

  10.1021/acs.joc.5b02084
• 作为产物：
  描述：

  对甲氧基苯乙酮 、 S-叔丁基亚磺酰胺 在 titanium(IV) isopropylate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以76%的产率得到(S)-N-(1-(4-methoxyphenyl)ethylidene)-2-methylpropane-2-sulfinamide
  参考文献：
  名称：

  含两个立体原子的α-氨基次膦酸酯的简明首次合成，可生成光学纯的α-氨基-H-次膦酸。

  摘要：

  DOI：

  10.1002/chem.200800690

文献信息

• Asymmetric Aldol–Tishchenko Reaction of Sulfinimines
  作者：Vera M. Foley、Christina M. McSweeney、Kevin S. Eccles、Simon E. Lawrence、Gerard P. McGlacken

  DOI：10.1021/acs.orglett.5b02919

  日期：2015.11.20

  Methods for the preparation of 1,3-amino alcohols and their derivatives containing two stereogenic centers usually involve a two-step installation of the chiral centers. An aldol–Tishchenko reaction of chiral sulfinimines which involves the first reported reduction of a C═N in this type of reaction is described. Two and even three chiral centers can be installed in one synthetic step, affording anti-1

  包含两个立体生成中心的1,3-氨基醇及其衍生物的制备方法通常涉及手性中心的两步安装。描述了手性亚胺的aldol-Tishchenko反应，该反应首次报道了这类反应中C═N的还原。可以在一个合成步骤中安装两个甚至三个手性中心，从而以良好的非对映体和对映体选择性提供抗-1,3-氨基醇。
• Diastereoselective Hydrosilylation of <i>N</i> -(<i>tert</i> -Butylsulfinyl)imines Catalyzed by Zinc Acetate
  作者：Anna Adamkiewicz、Jacek Mlynarski

  DOI：10.1002/ejoc.201501318

  日期：2016.2

  An efficient zinc-catalyzed diastereoselective hydrosilylation of N-(tert-butylsulfinyl)imines has been developed that does not require the use of ligands or noble metals. A variety of N-(tert-butylsulfinyl)imines were reduced by this protocol in the presence of a catalytic amount of zinc acetate (5 mol-%) to provide the corresponding secondary amines in high yields with excellent diastereoselectivities

  已经开发出一种高效的锌催化非对映选择性氢化硅烷化 N-（叔丁基亚磺酰基）亚胺，不需要使用配体或贵金属。在催化量的乙酸锌 (5 mol-%) 存在下，通过该方案还原了各种 N-（叔丁基亚磺酰基）亚胺，以高产率提供相应的仲胺，并具有出色的非对映选择性（高达 98 % de ）。通过使用三乙氧基硅烷作为有效的氢源，这种实验上简单的催化过程很容易适用于芳族和脂肪族胺的合成。
• Copper-catalyzed asymmetric allylation of chiral N-tert-butanesulfinyl imines: dual stereocontrol with nearly perfect diastereoselectivity
  作者：Yi-Shuang Zhao、Qiang Liu、Ping Tian、Jing-Chao Tao、Guo-Qiang Lin

  DOI：10.1039/c5ob00322a

  日期：——

  Copper-catalyzed asymmetric allylation of chiral N-tert-butanesulfinyl imines has been described. Dual stereocontrol, through the combination of a chiral auxiliary and a chiral copper complex, has played an important role in achieving the nearly perfect diastereoselectivities (all dr > 99 : 1), especially for ketimine substrates.

  已经描述了铜催化的手性N-叔-丁烷亚磺酰基亚胺的不对称烯丙基化。通过手性助剂和手性铜配合物的结合，双重立体控制在实现近乎完美的非对映选择性（所有dr> 99：1）方面起着重要作用，尤其是对于酮亚胺底物。
• Zinc-Mediated Asymmetric Additions of Dialkylphosphine Oxides to α,β-Unsaturated Ketones and <i>N</i>-Sulfinylimines
  作者：Depeng Zhao、Lijuan Mao、Dongxu Yang、Rui Wang

  DOI：10.1021/jo1014917

  日期：2010.10.15

  A catalyst was synthesized on the basis of Trost's dinuclear catalyst characterized by working well without pyridine in the present phospha-Michael reaction Nevertheless, the presence of pyridine is still advantageous in the present system The substrate scope was successfully extended to enones employing diallyl phosphine oxide as a nucleophile Excellent yields and enantioselectivities (up to >99% ee) wine achieved for a wide scope of enones employing the catalyst under mild conditions The detailed reaction mechanism is also discussed hetein Finally. the unprecedented asymmetric additions of dialkylphosphine oxides to N-sulfinylumines were achieved by using Et2Zn as a base
• Preparation of <i>anti</i> -1,3-Amino Alcohol Derivatives through an Asymmetric Aldol-Tishchenko Reaction of Sulfinimines
  作者：Pamela Mackey、Rafael Cano、Vera M. Foley、Gerard P. McGlacken

  DOI：10.1002/0471264229.os094.19

  日期：——