4-methanesulfonamidocyclopentene | 216578-29-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 4-methanesulfonamidocyclopentene
• 英文别名: N-(cyclopent-3-en-1-yl)methanesulfonamide；N-cyclopent-3-en-1-ylmethanesulfonamide
• CAS: 216578-29-9
• 化学式: C₆H₁₁NO₂S
• 分子量: 161.225
• InChiKey: WETPNTLDIXATLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-methanesulfonamidocyclopentene 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 (1R,3R,5S)-N-(6-Oxa-bicyclo[3.1.0]hex-3-yl)-methanesulfonamide
  参考文献：
  名称：

  4-氨基环戊-2-烯-1-醇的新途径：4-氨基取代的环戊烯氧化物的合成和对映选择性重排

  摘要：

  描述了用于碳环核苷类似物合成的4-氨基环戊-2-en-1-醇（90％ee）的不对称合成的新途径。该方法涉及立体选择性制备顺式4-氨基取代的环戊烯氧化物和随后手性碱介导的重排成相应的烯丙基醇。给出了4-氨基取代的环戊烯环氧化的合成和立体选择性的全部细节。

  DOI：

  10.1016/s0040-4020(00)00911-x
• 作为产物：
  描述：

  在 盐酸 、 4-二甲氨基吡啶 、 reflux 、 水 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 4-methanesulfonamidocyclopentene
  参考文献：
  名称：

  Synthesis and enantioselective rearrangement of 4-amino-substituted cyclopentene oxides

  摘要：

  Several N-mono- and diprotected alkenes have been prepared and the, stereoselectivity of their epoxidation has been investigated: N-monoprotected alkenes give cis epoxides preferentially (due to hydrogen bonding directed epoxidations) whereas N-diprotected alkenes produce trans epoxides exclusively (due to steric effects). Chiral lithium amide base-mediated rearrangement of a cis-monoprotected epoxide generated the corresponding amino-cyclopentenol in good yield and with an enantiomeric excess of 60%. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01821-8

文献信息

• Designing Degradable Polymers from Tricycloalkenes via Complete Cascade Metathesis Polymerization
  作者：Yongkang Yang、Yunhyeong Cho、Tae‐Lim Choi

  DOI：10.1002/anie.202400235

  日期：2024.4.24

  Cascade metathesis polymerization has been developed as a promising method to synthesize complex but well‐defined polymers from monomers containing multiple reactive functional groups. However, this approach has been limited to the monomers involving simple alkene/alkyne moieties or produced mainly non‐degradable polymers. In this study, we demonstrate a complete cascade ring‐opening/ring‐closing metathesis polymerization (RORCMP) using various tricycloalkenes and two strategies for the efficient degradation. Through rational design of tricycloalkene monomers, the structure and reactivity relationship was explored. For example, tricycloalkenes with trans configuration in the central ring enabled faster and better selective cascade RORCMP than the corresponding cis isomers. Also, a 4‐substituted cyclopentene moiety in the monomers significantly enhanced the overall cascade RORCMP performance, with the maximum turnover number (TON) reaching almost 10,000 and molecular weight up to 170 kg/mol using an amide‐containing monomer. Furthermore, we achieved one‐shot cascade multiple olefin metathesis polymerization using tricycloalkenes and a diacrylate, to produce new highly A,B‐alternating copolymers with full degradability. Lastly, we successfully designed xylose‐based tricycloalkenes to give well‐defined polymers that underwent ultra‐fast and complete degradation under mild conditions.