(R_S,E)-2-methyl-N-­(naphthalen-2-ylmethylene)propane-­2-­sulfinamide | 336105-26-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R_S,E)-2-methyl-N-­(naphthalen-2-ylmethylene)propane-­2-­sulfinamide
• 英文别名: (NE,R)-2-methyl-N-(naphthalen-2-ylmethylidene)propane-2-sulfinamide
• CAS: 336105-26-1
• 化学式: C₁₅H₁₇NOS
• 分子量: 259.372
• InChiKey: UBZWVPBSFYHVOS-QIPHDZALSA-N

物化性质

• 沸点：
  431.8±28.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  48.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R_S,E)-2-methyl-N-­(naphthalen-2-ylmethylene)propane-­2-­sulfinamide 在 盐酸 、 disodium hydrogenphosphate 、 sodium amalgam 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 为溶剂， 反应 1.75h， 生成 (S)-2-fluoro-1-(naphthalen-2-yl)ethanamine hydrochloride
  参考文献：
  名称：

  Stereoselective Nucleophilic Monofluoromethylation of N-(tert-Butanesulfinyl)imines with Fluoromethyl Phenyl Sulfone

  摘要：

  Highly stereoselective nucleophilic monofluoromethylation of (R)-(tert-butanesulfinyl)imines with fluoromethyl phenyl sulfone was achieved to afford alpha-monofluoromethylamines with a nonchelation-controlled stereoselectivity mode. By using the same chemistry, (R)-(tert-butanesulfinyl)imines bearing a terminal tosylate (M) group can be converted to alpha-monofluoromethylated cyclic secondary amines with high stereoselectivity.

  DOI：

  10.1021/ol060322t
• 作为产物：
  描述：

  2-萘甲醛 、 (R)-(+)-叔丁基亚磺酰胺 在 titanium(IV) isopropylate 作用下， 以 乙腈 为溶剂， 反应 0.17h， 生成 (R_S,E)-2-methyl-N-­(naphthalen-2-ylmethylene)propane-­2-­sulfinamide
  参考文献：
  名称：

  一锅微波促进叔丁亚磺酰亚胺从醛中合成腈

  摘要：

  描述了一种简便的单锅法，通过微波促进、协同消除叔丁亚磺酰基保护的亚胺中的叔丁亚磺酸，从醛中合成腈。温和的反应条件表现出广泛的官能团相容性，并以良好的分离产率 (69-87%) 生成产物。该方法为合成各种官能化腈提供了一种快速而温和的方法。

  DOI：

  10.1055/s-2007-990805

文献信息

• Water-Accelerated Organometallic Chemistry: Alkyne Carboalumination – Sulfinimine Addition and Asymmetric Synthesis of Allylic Amines
  作者：Peter Wipf、Ruth L. Nunes、Seth Ribe

  DOI：10.1002/1522-2675(200210)85:10<3478::aid-hlca3478>3.0.co;2-e

  日期：2002.10

  addition to enantiomerically enriched (tert-butyl)- and (para-tolyl)sulfinimines. This new in situ protocol produces two new CC bonds. Chiral allylic sulfinamides are obtained in high diastereoselectivity and in good yield. Cleavage of the chiral auxiliary leads to synthetically useful allylic amine building blocks, and facile oxidative degradation of the alkene moiety can be used as an approach toward

  在催化性 Cp2ZrCl2 和 H2O 存在下，炔烃的碳铝化得到乙烯基丙烷中间体，其在随后添加到对映体富集的（叔丁基）和（对甲苯基）亚磺酰亚胺中充当亲核试剂。这种新的原位协议产生了两个新的 CC 债券。以高非对映选择性和良好收率获得手性烯丙基亚磺酰胺。手性助剂的裂解导致合成有用的烯丙胺结构单元，烯烃部分的易氧化降解可用作获得氨基酸衍生物和分配绝对构型的方法。
• Room-Temperature Highly Diastereoselective Zn-Mediated Allylation of Chiral <i>N</i>-<i>tert</i>-Butanesulfinyl Imines:  Remarkable Reaction Condition Controlled Stereoselectivity Reversal
  作者：Xing-Wen Sun、Ming-Hua Xu、Guo-Qiang Lin

  DOI：10.1021/ol062216x

  日期：2006.10.1

  the highly diastereoselective synthesis of chiral homoallylic amines by Zn-mediated allylation of chiral N-tert-butanesulfinyl imines at room temperature was developed. By simply tuning the reaction conditions, the method allows the achievement of a highly remarkable opposite stereocontrol, affording the desired stereochemical outcome in good yield and with excellent diastereoselectivity (up to 98%

  [反应：见正文]开发了一种在室温下通过锌介导的手性N-叔丁烷亚磺酰基亚胺的高非对映选择性合成手性均胺的有效方法。通过简单地调节反应条件，该方法可以实现高度显着的相反立体控制，以良好的收率和出色的非对映选择性（高达98％dr）提供所需的立体化学结果。用N-亚磺酰基酮亚胺，也可以制备相应的含季碳的手性均烯丙基胺。
• Stereoselective Synthesis of α-Silylamines by the Direct Addition of Silyl Anions to Activated Imines
  作者：David M. Ballweg、Rebecca C. Miller、Danielle L. Gray、Karl A. Scheidt

  DOI：10.1021/ol050244u

  日期：2005.3.1

  A highly efficient stereoselective synthesis of unusual alpha-silylamines via a direct silyl anion addition reaction is reported. This approach is convergent and avoids any problematic aza-Brook shifts of the anionic intermediates. The use of enantiopure tert-butanesulfinyl imines as the electrophiles affords exceedingly high levels of diastereocontrol for the newly formed stereogenic carbon.
• Cycloaddition of Chiral <i>tert</i>-Butanesulfinimines with Trimethylenemethane
  作者：George Procopiou、William Lewis、Gareth Harbottle、Robert A. Stockman

  DOI：10.1021/ol400720b

  日期：2013.4.19

  The cycloaddition of chiral tert-butanesulfinimines with trimethylenemethane is found to give facile access to methylene-pyrrolidines with good yields and diastereoselectivities. The full scope of the cycloaddition is explored, and a range of transformations of the formed methylenepyrrolidines to give a range of functionalized chiral pyrrolidines is presented.
• Facile Synthesis of Chiral α-Difluoromethyl Amines fromN-(tert-Butylsulfinyl)aldimines
  作者：Ya Li、Jinbo Hu

  DOI：10.1002/anie.200501769

  日期：2005.9.12