(R)-(-)-N-(1-phenylpentylidene)-2-methylpropane-2-sulfinamide | 220263-61-6

• 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: (R)-(-)-N-(1-phenylpentylidene)-2-methylpropane-2-sulfinamide
• 英文别名: (R_S)-2-methyl-N-(1-phenylpentylidene)propane-2-sulfinamide；(R,E)-2-methyl-N-(1-phenylpentylidene)propane-2-sulfinamide；(NE,R)-2-methyl-N-(1-phenylpentylidene)propane-2-sulfinamide
• CAS: 220263-61-6
• 化学式: C₁₅H₂₃NOS
• 分子量: 265.42
• InChiKey: MTVGCWWPLDORHA-QRURKXGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 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)-(-)-N-(1-phenylpentylidene)-2-methylpropane-2-sulfinamide 在 ruthenium trichloride sodium periodate 、 正丁基锂 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 、 水 、 乙腈 为溶剂， 生成 (R)-2-(2-Methyl-propane-2-sulfonylamino)-2-phenyl-hexanoic acid
  参考文献：
  名称：

  叔丁烷亚磺酰基酮亚胺不对称合成预保护的α，α-二取代氨基酸

  摘要：

  描述了一种不对称合成预保护的α，α-二取代氨基酸的方法。5- Methylfuryllithium加入到亚硫酮亚胺1中阿尔梅的存在3，得到亚磺酰胺2在75-97％的产率和非对映选择性与范围从75:25至99：1。用的RuCl随后氧化3 /的NaIO 4，得到叔-butanesulfonyl（总线）保护的α，α-二取代的氨基酸3在62-69％的产率。总线保护的氨基酸容易形成酰胺键，此后可以用TfOH / CH 2 Cl 2除去总线基团，得到游离胺。

  DOI：

  10.1016/s0040-4039(00)02300-5
• 作为产物：
  描述：

  苯戊酮 、 (R)-(+)-叔丁基亚磺酰胺 在 titanium(IV) tetraethanolate 作用下， 以79%的产率得到(R)-(-)-N-(1-phenylpentylidene)-2-methylpropane-2-sulfinamide
  参考文献：
  名称：

  在氢化物还原Diastereofacial选择性逆转ñ -叔-Butanesulfinyl亚胺

  摘要：

  在含2％水的THF中用NaBH 4还原各种N-叔丁烷亚磺酰基亚胺，从而以高收率和非对映选择性提供相应的仲亚磺酰胺。通过使用相同的亚磺酰基亚胺原料并将还原剂更改为L-Selectride，可以有效地逆转立体选择性，从而以高收率和选择性提供相反的产物非对映异构体。

  DOI：

  10.1021/jo0609834

文献信息

• Site-Specific Synthesis of β-Fluorinated γ-Butyrolactams via Decarboxylative Fluorination of β-Carboxyl-γ-Butyrolactams
  作者：Supasorn Phae-nok、Manat Pohmakotr、Chutima Kuhakarn、Vichai Reutrakul、Darunee Soorukram

  DOI：10.1002/ejoc.201900685

  日期：2019.8.7

  The direct and site‐specific synthesis of β‐fluorinated γ‐butyrolactams via AgNO3 mediated decarboxylative fluorination of β‐carboxyl‐γ‐butyrolactams using Selectfluor® as a fluorine source was described. The β‐fluorinated γ‐butyrolactams including chiral derivatives were obtained in moderate to good yields.

  描述了使用Selectfluor®作为氟源，通过AgNO 3介导的β-羧基-γ-丁内酰胺的直接脱羧氟化反应，直接合成β-氟化的γ-丁内酰胺。包括手性衍生物在内的β-氟化γ-丁内酰胺的收率中等至良好。
• Synthesis of Enantiomerically Pure <i>N</i>-<i>tert</i>-Butanesulfinyl Imines (<i>tert</i>-Butanesulfinimines) by the Direct Condensation of <i>tert</i>-Butanesulfinamide with Aldehydes and Ketones
  作者：Guangcheng Liu、Derek A. Cogan、Timothy D. Owens、Tony P. Tang、Jonathan A. Ellman

  DOI：10.1021/jo982059i

  日期：1999.2.1

  Experimental details for the first general methods for the one-step preparation of N-tert-butanesulfinyl imines (tert-butanesulfinimines) (2) from aldehydes and ketones is described. To effect the condensations of tert-butanesulfinamide (1) with aldehydes, the Lewis acidic dehydrating agents MgSO4, CuSO4, or Ti(OEt)(4) are employed. Aldehyde condensations mediated by MgSO4 proceed in high yields (84-96%) when an excess of aldehyde is used. In contrast, only a slight excess of aldehyde (1.1 equiv) relative to tert-butanesulfinamide provides sulfinimines in high yields when the more Lewis acidic dehydrating agent CuSO4 is used. The CuSO4-mediated procedure is effective for a wide range of aldehydes, including sterically demanding aldehydes, such as isobutyraldehyde (90%), and electron-rich aldehydes, such as p-anisaldehyde (81%). The still more Lewis acidic Ti(OEt)(4) and Ti(O-i-Pr)(4) also afford N-tert-butanesulfinyl aldimines from especially unreactive aldehydes, such as pivaldehyde (82%). In addition, Ti(OEt)(4) is effective for the condensation of I with ketones to afford a wide range of N-tert-butanesulfinyl ketimines in good yields (77-91%). For sulfinyl ketimines derived from methyl or n-alkyl phenyl ketones and methyl or n-alkyl isopropyl ketones, only the E isomer is detected by H-1 and C-13 NMR in CDCl3. For those cases where the difference in steric demand about the imine is very small, such as for 2-hexanone, high E/Z ratios are still observed (5:1).
• Reversal of Diastereofacial Selectivity in Hydride Reductions of <i>N</i>-<i>tert</i>-Butanesulfinyl Imines
  作者：John T. Colyer、Neil G. Andersen、Jason S. Tedrow、Troy S. Soukup、Margaret M. Faul

  DOI：10.1021/jo0609834

  日期：2006.9.1

  same sulfinyl imine starting materials and changing the reductant to L-Selectride, the stereoselectivity could be efficiently reversed to afford the opposite product diastereomer in high yield and selectivity.

  在含2％水的THF中用NaBH 4还原各种N-叔丁烷亚磺酰基亚胺，从而以高收率和非对映选择性提供相应的仲亚磺酰胺。通过使用相同的亚磺酰基亚胺原料并将还原剂更改为L-Selectride，可以有效地逆转立体选择性，从而以高收率和选择性提供相反的产物非对映异构体。
• Asymmetric synthesis of pre-protected α,α-disubstituted amino acids from tert-butanesulfinyl ketimines
  作者：George Borg、Masao Chino、Jonathan A Ellman

  DOI：10.1016/s0040-4039(00)02300-5

  日期：2001.2

  method for the asymmetric synthesis of pre-protected α,α-disubstituted amino acids is described. 5-Methylfuryllithium is added into sulfinyl ketimines 1 in the presence of AlMe3 to afford the sulfinamides 2 in 75–97% yields and with diastereoselectivities ranging from 75:25 to 99:1. Subsequent oxidation with RuCl3/NaIO4 affords tert-butanesulfonyl (Bus)-protected α,α-disubstituted amino acids 3 in 62–69%

  描述了一种不对称合成预保护的α，α-二取代氨基酸的方法。5- Methylfuryllithium加入到亚硫酮亚胺1中阿尔梅的存在3，得到亚磺酰胺2在75-97％的产率和非对映选择性与范围从75:25至99：1。用的RuCl随后氧化3 /的NaIO 4，得到叔-butanesulfonyl（总线）保护的α，α-二取代的氨基酸3在62-69％的产率。总线保护的氨基酸容易形成酰胺键，此后可以用TfOH / CH 2 Cl 2除去总线基团，得到游离胺。