1-benzylamino-3-buten-2-ol | 125582-80-1

• 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: 1-benzylamino-3-buten-2-ol
• 英文别名: 1-(Benzylamino)but-3-en-2-ol
• CAS: 125582-80-1
• 化学式: C₁₁H₁₅NO
• mdl: MFCD09260617
• 分子量: 177.246
• InChiKey: XMXIYNWVRYFIEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzylamino-3-buten-2-ol 在 triphenylphosphine dibromide 1:1 addition complex 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以62%的产率得到1-benzyl-2-vinylaziridine
  参考文献：
  名称：

  Dynamic Kinetic Asymmetric Cycloadditions of Isocyanates to Vinylaziridines

  摘要：

  The first examples of the use of racemic vinylaziridines in a Pd-catalyzed dynamic kinetic asymmetric transformation have been examined. Optimization studies of the Pd-catalyzed addition of vinylaziridines to isocyanates revealed that the chiral ligand between trans-1,2-diaminocyclohexane and 2-diphenylphosphino-1-naphthoic acid is superior to that involving 2-diphenylphosphino benzoic acid. Surprisingly, high ee's required the use of an acid whose pKa was about 4.7 +/- 0.1 as a cocatalyst. Both acetic acid and hydroxybenzotriazole meet this requirement. Less electrophilic isocyanates (e.g., benzyl, p-methoxyphenyl) gave higher ee's than more electrophilic ones (phenyl or benzoyl). Both N-benzyl and N-arylaziridines react well to give good yields and ee's, whereas N-tosylaziridines gave lower ee's. A 1,1-disubstituted aziridine led to the formation of a tertiary C-N bond with ee's comparable to the formation of the secondary C-N bond. The products were easily reduced almost quantitatively to the sensitive imidazolidines which can be readily hydrolyzed to the vicinal diamines. The reactivity pattern is consistent with a Curtin-Hammett situation wherein the enantiodiscriminating event is the cyclization of a rapidly equilibrating dynamic pi-allyl palladium intermediate.

  DOI：

  10.1021/ja037450m
• 作为产物：
  描述：

  在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以15.15 g的产率得到1-benzylamino-3-buten-2-ol
  参考文献：
  名称：

  Dynamic Kinetic Asymmetric Cycloadditions of Isocyanates to Vinylaziridines

  摘要：

  The first examples of the use of racemic vinylaziridines in a Pd-catalyzed dynamic kinetic asymmetric transformation have been examined. Optimization studies of the Pd-catalyzed addition of vinylaziridines to isocyanates revealed that the chiral ligand between trans-1,2-diaminocyclohexane and 2-diphenylphosphino-1-naphthoic acid is superior to that involving 2-diphenylphosphino benzoic acid. Surprisingly, high ee's required the use of an acid whose pKa was about 4.7 +/- 0.1 as a cocatalyst. Both acetic acid and hydroxybenzotriazole meet this requirement. Less electrophilic isocyanates (e.g., benzyl, p-methoxyphenyl) gave higher ee's than more electrophilic ones (phenyl or benzoyl). Both N-benzyl and N-arylaziridines react well to give good yields and ee's, whereas N-tosylaziridines gave lower ee's. A 1,1-disubstituted aziridine led to the formation of a tertiary C-N bond with ee's comparable to the formation of the secondary C-N bond. The products were easily reduced almost quantitatively to the sensitive imidazolidines which can be readily hydrolyzed to the vicinal diamines. The reactivity pattern is consistent with a Curtin-Hammett situation wherein the enantiodiscriminating event is the cyclization of a rapidly equilibrating dynamic pi-allyl palladium intermediate.

  DOI：

  10.1021/ja037450m

文献信息

• [EN] METHODS FOR PREPARING FLUOROALKYL ARYLSULFINYL COMPOUNDS AND FLUORINATED COMPOUNDS THERETO<br/>[FR] PROCÉDÉS DE PRÉPARATION DE COMPOSÉS FLUOROALKYLE ARYLSULFINYLÉS ET COMPOSÉS FLUORÉS APPARENTÉS
  申请人：IM & T RES INC

  公开号：WO2010022001A1

  公开（公告）日：2010-02-25

  Novel preparative methods for fluoroalkyl arylsulfinyl compounds are disclosed. Fluorinated compounds as useful fluorinated compounds, intermediates, or builing blocks are disclosed. Useful applications of the fluoroalkyl arylsulfinyl compounds are shown.

  揭示了用于制备氟烷基芳基磺酰基化合物的新型制备方法。公开了氟化合物作为有用的氟化合物、中间体或构建块。展示了氟烷基芳基磺酰基化合物的有用应用。
• A Synthetic Strategy toward Eight-Membered Cyclic Amines by Cycloetherification and Claisen Rearrangement
  作者：Seo-Jung Han、Marchello A. Cavitt、Brian M. Stoltz

  DOI：10.1021/acs.orglett.1c00763

  日期：2021.5.7

  Eight-membered nitrogen-containing heterocycles were straightforwardly produced by a nickel-catalyzed cycloetherification and subsequent Claisen rearrangement of secondary and tertiary alcohols. In particular, a one-pot transformation was achieved with tertiary alcohols in moderate to good yields. This operationally simple reaction is tolerant of many functional groups and applicable to the synthesis

  通过镍催化的环醚化和随后的仲醇和叔醇的克莱森重排直接产生八元含氮杂环。特别是，用叔醇以中等至良好的产率实现了一锅法转化。这种操作简单的反应可耐受多种官能团，适用于合成各种中环含氮杂环。
• Methods For Preparing Fluoroalkyl Arylsulfinyl Compounds And Fluorinated Compounds Thereto
  申请人：Umemoto Teruo

  公开号：US20110190511A1

  公开（公告）日：2011-08-04

  Novel preparative methods for fluoroalkyl arylsulfinyl compounds are disclosed. Fluorinated compounds as useful fluorinated compounds, intermediates, or builing blocks are disclosed. Useful applications of the fluoroalkyl arylsulfinyl compounds are shown.

  本发明揭示了一种用于制备氟烷基芳基亚磺酰化合物的新型制备方法。本发明还揭示了氟化合物作为有用的氟化合物、中间体或构建块。同时，本发明还展示了氟烷基芳基亚磺酰化合物的有用应用。
• Methods for Preparing Fluoroalkyl Arylsulfinyl Compounds and Fluorinated Compounds Thereto
  申请人：Umemoto Teruo

  公开号：US20100152463A1

  公开（公告）日：2010-06-17

  Novel preparative methods for fluoroalkyl arylsulfinyl compounds are disclosed. Fluorinated compounds as useful fluorinated compounds, intermediates, or building blocks are disclosed. Useful applications of the fluoroalkyl arylsulfinyl compounds are shown.

  本发明公开了用于制备氟烷基芳基磺酰基化合物的新型制备方法。本发明还公开了作为有用的氟化合物、中间体或构建块的氟化合物。本发明还展示了氟烷基芳基磺酰基化合物的有用应用。
• Aminolead compounds as a new reagent for regioselective ring opening of epoxides
  作者：Jun-ichi Yamada、Masatoshi Yumoto、Yoshinori Yamamoto

  DOI：10.1016/s0040-4039(01)80704-8

  日期：1989.1