S,S-diphenyl-N-(2-(phenylsulfonyl)ethyl)sulfilimine | 58940-90-2

• 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,S-diphenyl-N-(2-(phenylsulfonyl)ethyl)sulfilimine
• 英文别名: diphenyl-N-(-2-phenylsulfonylethyl)sulfimide；Diphenyl-N-(2-phenylsulfonylethyl)-sulfilimin；2-(benzenesulfonyl)ethylimino-diphenyl-λ4-sulfane
• CAS: 58940-90-2
• 化学式: C₂₀H₁₉NO₂S₂
• 分子量: 369.508
• InChiKey: GPIGHDZVTAMTEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.38
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  46.5
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  S,S-diphenyl-N-(2-(phenylsulfonyl)ethyl)sulfilimine 在 氧气 作用下， 反应 36.0h， 生成 N-(2-(2-phenylsulfonyl)ethyl)acetamide
  参考文献：
  名称：

  Reaction of chromium (Fischer) carbenes and sulfilimines

  摘要：

  The photochemical reactions of alkoxychromium (Fischer) carbenes and sulfilimines lead to imidates in fair to excellent yields. Aromatic, heteroaromatic, and alkylsulfilimines, the latter bearing functional groups such as cyano, sulfone, ether, ester, and dioxolane groups, gave the corresponding imidates in good to excellent yield. However, acyl- and sulfonyl-substituted sulfilimines did not react with chromium carbenes, except for sulfilimines bearing ethoxycarbonyl and phtalimidylamino groups. A variety of differently substituted chromium carbene complexes bearing alkyl, cycloalkyl, styryl, allyl, and alkynyl groups attached either at the carbene carbon or at the oxygen also gave imidates in good yields. For alpha,beta-unsaturated carbenes, the exclusive 1,2-addition of the sulfilimine nitrogen was observed at room temperature, in contrast to the behavior of other nitrogen nucleophiles which are reported to add in 1,4-fashion under these reaction conditions. In turn, optically active imidates of the type ArN=C(OR*)Me [R* = chiral substituent derived from (R)-(+)-1-phenyl-1-butanol, l-(-)-menthol, (1S)-endo-(-)-borneol, and (1R)-(-)-myrtenol] can be prepared efficiently by utilizing the corresponding chiral alkoxy group on the earbene moiety. The reactions above also occur in the dark but reaction times are considerably longer. N-Halosulfilimines reacted with alkoxychromium carbenes to yield N-acylsulfilimines instead of the expected N-haloimidates. Based upon a set of thermal and photochemical reactions between N-haloimidates and diphenyl sulfide in the absence of chromium complexes, the complex (CO)5CrNCMe is proposed to be responsible for this novel reaction of N-haloimidates and diphenyl sulfide.

  DOI：

  10.1021/jo00067a020
• 作为产物：
  描述：

  N-(phenylthio)benzamide 在 copper(II) trimethyl acetate monohydrate 、 硫酸 、 氧气 作用下， 以 氯仿 、 1,2-二氯乙烷 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 反应 34.0h， 生成 S,S-diphenyl-N-(2-(phenylsulfonyl)ethyl)sulfilimine
  参考文献：
  名称：

  铜催化亚磺酰胺的 S-芳基化合成磺亚胺

  摘要：

  在此，提出了一种前所未有的通过亚磺酰胺的铜催化 Chan-Lam 型偶联合成硫亚胺的路线。这种新型转化成功的关键是 S(II) 次磺酰胺的化学选择性S-芳基化形成 S(IV) 硫亚胺，从而克服了竞争性的、热力学上更有利的 C-N 键形成，无需改变硫的氧化态。计算表明，选择性源于选择性金属转移事件，其中双齿次磺酰胺通过硫和氧原子的配位有利于S-芳基化途径。温和且环境友好的催化条件可实现广泛的官能团相容性，从而可以有效制备各种二芳基或烷基芳基硫亚胺。 Chan-Lam 偶联过程还可以容忍烯基硼酸作为偶联伙伴，以提供烯基芳基硫亚胺，这是一类不能通过传统亚胺化策略直接合成的支架。苯甲酰基保护基团可以方便地从产物中除去，进而可以很容易地转化为几种S(IV)和S(VI)衍生物。

  DOI：

  10.1021/jacs.2c12947

文献信息

• One step synthesis of aziridines by the Michael type addition of free sulfimides
  作者：Naomichi Furukawa、Toshiaki Yoshimura、Masami Ohtsu、Takeshi Akasaka、Shigeru Oae

  DOI：10.1016/0040-4020(80)85027-7

  日期：1980.1

  the corresponding aziridine but diphenyl-N-2-cyano or N-2-phenylsulfonylethylsulfimide, a simple Michael adduct When optically active (+)-(R)-o-methoxyphenyiphenyl free sulfimide was treated with such an α,β-unsaturated carbonyl compound as benzalacetopbenone, an optically active 2-acylazindine, i.e., (-)-trans-2-benzoyl-3-phenylaziridine was obtained in ca 30% optical purity and its absolute configuration

  进行了将二苯基N-未取代的硫酰亚胺（游离的硫酰亚胺）向各种亲电烯烃的迈克尔型加成反应。与顺式和反式-二苯甲酰基乙烯，富马酸二甲酯，马来酸二甲酯，苯并乙酰苯甲酮和苯并丙酮的反应主要得到相应的反式-2-酰基氮丙啶和反式-烯酮。然而，苯基乙烯基砜或丙烯腈不提供相应的氮丙啶，而是提供二苯基-N-2-氰基或N-2-苯基磺酰基乙基磺酰亚胺，这是一种简单的迈克尔加成物，当其具有光学活性（+）-（R）-o时用α，β-不饱和羰基化合物如苯甲酰基苯甲酮处理无甲氧基苯并苯基的硫化亚胺，得到旋光性2-酰基二嗪，即，以约30％的光学纯度得到（-）-反式-2-苯甲酰基-3-苯基氮丙啶，并且通过化学转化将其绝对构型指定为（2 R，3 S）到构型众所周知的2-苯基-2-苯甲酰氨基-1-乙醇，或者将其CD光谱与（1 R，2 R）-进行比较1-苯基-2-苯甲酰基-环丙烷。同时，（-）-（S）-o发现无甲氧基苯基苯基的亚硫酰亚
• The Michael Type Addition of Free Sulfilimine
  作者：Naomichi FURUKAWA、Shigeru OAE、Toshiaki YOSHIMURA

  DOI：10.1055/s-1976-23945

  日期：——
• FURUKAWA N.; OAE S., SYNTHESIS <SYNT-BF>, 1976, NO 1, 30-32
  作者：FURUKAWA N.、 OAE S.

  DOI：——

  日期：——