(S)-2-methyl-N-(1-phenylpropylidene)propane-2-sulfinamide | 874291-47-1

• 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: (S)-2-methyl-N-(1-phenylpropylidene)propane-2-sulfinamide
• CAS: 874291-47-1
• 化学式: C₁₃H₁₉NOS
• 分子量: 237.366
• InChiKey: CBZHLXIBLDBOIU-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  16.0
• 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：
  29.43
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (S)-2-methyl-N-(1-phenylpropylidene)propane-2-sulfinamide 在 三乙氧基硅烷 、 zinc diacetate 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以75%的产率得到(S_S,S)-N-(tert-butanesulfinyl) 1-phenylpropylamine
  参考文献：
  名称：

  乙酸锌催化N-(叔丁基亚磺酰基)亚胺的非对映选择性氢化硅烷化

  摘要：

  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。

  DOI：

  10.1002/ejoc.201501318
• 作为产物：
  描述：

  苯丙酮 、 S-叔丁基亚磺酰胺 在 titanium(IV) tetraethanolate 作用下， 生成 (S)-2-methyl-N-(1-phenylpropylidene)propane-2-sulfinamide
  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

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。
• Asymmetric Synthesis of Homoallylic Amines Bearing Adjacent Stereogenic Centers by Addition of Substituted Allylic Zinc Reagents to N-<i>tert</i>-Butanesulfinylimines
  作者：Leleti Rajender Reddy、Bin Hu、Mahavir Prashad、Kapa Prasad

  DOI：10.1021/ol800998u

  日期：2008.7.17

  diastereoselective addition of substituted racemic allylic zinc reagents to chiral N- tert-butanesulfinylimines resulting in the formation of homoallylic amines is reported. This method is quite general and also efficient for the preparation of enantiomerically pure homoallylic amines bearing quaternary centers and also adjacent quaternary centers.

  据报道，向手性N-叔丁烷亚磺酰亚胺中高度非对映选择性地添加了取代的外消旋烯丙基锌试剂，导致形成了均烯丙基胺。该方法是非常通用的，并且对于制备带有季中心以及相邻的季中心的对映体纯的均烯丙基胺也是有效的。
• Asymmetric Total Synthesis of (+)-Epiibogamine Enabled by Three-Component Domino Michael/Michael/Mannich Annulation of <i>N</i>-Sulfinyl Metallosilylenamines
  作者：Po-Cheng Yu、Anupam Karmakar、William A. Sabbers、Femil Shajan、Rodrigo B. Andrade

  DOI：10.1021/acs.orglett.2c04287

  日期：2023.2.17

  The iboga alkaloids are promising antiaddictive and neuroregeneration candidates for medical treatment. There is a lack of studies for C20-epi iboga alkaloids due to the synthetic difficulties. Herein we report the shortest total synthesis of (+)-epiibogamine in seven steps from trimethyl orthobutyrate. The novel N-sulfinyl silylenamine reagent enabled the key step, with three-component domino Mic

  iboga 生物碱是有前途的抗上瘾和神经再生候选药物。由于合成困难，缺乏对 C20-epi iboga 生物碱的研究。在这里，我们报告了 (+)-epiibogamine 的最短全合成，分七步从原丁酸三甲酯开始。新型N-亚磺酰甲硅烷基胺试剂实现了关键步骤，三组分多米诺迈克尔/迈克尔/曼尼希环化为 1-氨基-2,4-二酯支架提供了四个新的手性中心，并以高产率获得异奎宁环（ 84%）和非对映选择性（>95:5 dr）。
• Bispidine‐Based <i>S</i>,<i>N</i>‐Chiral Ligands for Palladium‐Catalyzed Asymmetric Arylation of Cyclic <i>N</i>‐Sulfonyl Ketimines
  作者：Gonglin Li、Ruifeng Wang、Dong Ye、Maoping Pu、Xiaoming Feng、Lili Lin

  DOI：10.1002/ejoc.202400008

  日期：2024.3.11

  and stable bispidine-based S,N-chiral ligand was designed, complexing with Pd, to efficiently promote the asymmetric addition of arylboric acids to cyclic N-sulfonyl ketimines. The structure determination of ligand and ligand/PdCl2 catalyst, together with DFT calculations, clarify the origin of enantioselectivity as well as the reason of alkyl group on ligand affecting the stereoselectivity significantly

  设计了一种简单且稳定的新型双吡啶基S , N-手性配体，与Pd络合，有效促进芳基硼酸与环状N-磺酰酮亚胺的不对称加成。配体和配体/PdCl 2催化剂的结构测定以及DFT计算阐明了对映选择性的起源以及配体上的烷基显着影响立体选择性的原因。
• 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