2-(tert-butylsulfonyl)-2-propenyl alcohol | 134996-37-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 磺酰类
• 英文名称: 2-(tert-butylsulfonyl)-2-propenyl alcohol
• 英文别名: 2-(t-butylsulfonyl)-2-propenyl alcohol；2-Tert-butylsulfonylprop-2-en-1-ol
• CAS: 134996-37-5
• 化学式: C₇H₁₄O₃S
• 分子量: 178.252
• InChiKey: HRQTWMSMBSYXAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(tert-butylsulfonyl)-2-propenyl alcohol 在 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 3.5h， 生成 2-(t-Butylsulfonyl)-2-propenyloxycarbonyl-L-phenylalanine
  参考文献：
  名称：

  Amino-Protecting Groups Subject to Deblocking under Conditions of Nucleophilic Addition to a Michael Acceptor. Structure−Reactivity Studies and Use of the 2-(tert-Butylsulfonyl)-2-propenyloxycarbonyl (Bspoc) Group

  摘要：

  A new type of amino-protecting group is described in which a Michael acceptor is incorporated into the protectant so that treatment with a nucleophile will trigger deblocking. Comparison of various Michael accepters showed that for several key electron-withdrawing groups, the order of reactivity was C6H5SO2 > Me3CSO2 > COOEt > CsH5SO > C(6)H(4)NO(2-)p. The reactivity of the nucleophile. (e.g., primary and secondary aliphatic amines) followed an order related to both intrinsic basicity and steric effects. beta-Substituents in the Michael acceptor caused significant retardation of the deblocking process. The Bspoc function was chosen for initial elaboration into a practical system for use in peptide synthesis. Bspoc amino acid chlorides were used as coupling agents and silica-tethered secondary amines as deblocking agents. With the latter, deblocking occurs cleanly and no byproducts remain in the organic solvent in which the deblocking is executed.

  DOI：

  10.1021/jo982141d
• 作为产物：
  描述：

  3-Bromo-2-(tert-butylsulfonyl)-1-propene 在 sodium formate 作用下， 以 甲醇 为溶剂， 以68%的产率得到2-(tert-butylsulfonyl)-2-propenyl alcohol
  参考文献：
  名称：

  Amino-Protecting Groups Subject to Deblocking under Conditions of Nucleophilic Addition to a Michael Acceptor. Structure−Reactivity Studies and Use of the 2-(tert-Butylsulfonyl)-2-propenyloxycarbonyl (Bspoc) Group

  摘要：

  A new type of amino-protecting group is described in which a Michael acceptor is incorporated into the protectant so that treatment with a nucleophile will trigger deblocking. Comparison of various Michael accepters showed that for several key electron-withdrawing groups, the order of reactivity was C6H5SO2 > Me3CSO2 > COOEt > CsH5SO > C(6)H(4)NO(2-)p. The reactivity of the nucleophile. (e.g., primary and secondary aliphatic amines) followed an order related to both intrinsic basicity and steric effects. beta-Substituents in the Michael acceptor caused significant retardation of the deblocking process. The Bspoc function was chosen for initial elaboration into a practical system for use in peptide synthesis. Bspoc amino acid chlorides were used as coupling agents and silica-tethered secondary amines as deblocking agents. With the latter, deblocking occurs cleanly and no byproducts remain in the organic solvent in which the deblocking is executed.

  DOI：

  10.1021/jo982141d

文献信息

• Reagents for rapid peptide synthesis
  申请人：Research Corporation Technologies, Inc.

  公开号：US05221754A1

  公开（公告）日：1993-06-22

  This invention relates to compounds of the formula: ##STR1## wherein R is an electron withdrawing group; R.sub.1 is H or COZ; X.sub.1 and X.sub.2 are independently H, lower alkyl, aryl, aryl lower-alkyl or polystyrene or R and X.sub.1 taken together with the carbon atoms to which they are attached form a ring containing from 4 to 15 ring carbon atoms and may contain up to 2 heteroatoms, wherein the heteroatoms are O, S, or N; and Z is an amino acid residue, a peptide residue or a leaving group. The compounds of the present invention are adaptable as blocking or protecting groups for an amine composition useful in peptide synthesis. The present invention is also directed to a method of protecting an amino group of an organic molecule during a reaction which modifies a portion of the molecule other than the protected amino group.

  本发明涉及以下结构的化合物：##STR1## 其中R是一个电子吸引基团；R.sub.1是H或COZ；X.sub.1和X.sub.2独立地是H、较低的烷基、芳基、芳基较低烷基或聚苯乙烯，或者R和X.sub.1与它们附着的碳原子一起形成一个含有4到15个环碳原子并且可能含有最多2个杂原子的环，其中杂原子是O、S或N；Z是氨基酸残基、肽残基或离去基团。本发明的化合物可用作肽合成中有用的胺组成部分的阻断或保护基团。本发明还涉及在修改分子的除受保护的氨基团之外的部分时保护有机分子的氨基团的方法。
• Synthesis and use of amino acid fluorides as peptide coupling reagents
  申请人：Research Corporation Technologies, Inc.

  公开号：US05360928A1

  公开（公告）日：1994-11-01

  A compound of the formula ##STR1## or the acid fluoride salts thereof wherein BLK is an N-amino protecting group or hydrogen AA is an amino acid residue and X is H or a protecting group useful as a coupling agent in peptide synthesis.

  化合物的公式为##STR1##或其酸氟化物盐，在其中BLK是N-氨基保护基或氢，AA是氨基酸残基，X是H或作为肽合成中偶联剂有用的保护基。
• SYNTHESIS AND USE OF AMINO ACID FLUORIDES AS PEPTIDE COUPLING REAGENTS
  申请人：RESEARCH CORPORATION TECHNOLOGIES, INC.

  公开号：EP0496836A1

  公开（公告）日：1992-08-05
• EP0496836A4
  申请人：——

  公开号：EP0496836A4

  公开（公告）日：1993-05-05
• JPH0341088A
  申请人：——

  公开号：JPH0341088A

  公开（公告）日：1991-02-21