(S)-1-ethyl-2-heptynyl methanesulfonate | 1026258-29-6

• 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: (S)-1-ethyl-2-heptynyl methanesulfonate
• 英文别名: [(3S)-non-4-yn-3-yl] methanesulfonate
• CAS: 1026258-29-6
• 化学式: C₁₀H₁₈O₃S
• 分子量: 218.317
• InChiKey: SAPKBHFHFHZVKJ-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1-ethyl-2-heptynyl methanesulfonate 在 palladium dichloride 对苯醌 、 copper dichloride 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 20.0~40.0 ℃ 、2.07 MPa 条件下， 反应 12.0h， 生成 (R)-(+)-(E)-α-(1-chloropentylidene)-β-ethyl-N-benzyl-β-lactam
  参考文献：
  名称：

  PdCl₂-Catalyzed Efficient Transformation of Propargylic Amines to (E)-α-Chloroalkylidene-β-lactams

  摘要：

  The PdCl2-catalyzed cyclocarbonylation reaction of propargylic amines with CuCl2 and benzoquinone afforded (E)-alpha-chloroalkylidene-beta-lactams in moderate to good yields. The formation of the corresponding Z-isomers or five-membered products was not observed. The reaction of the readily available optically active propargylic amines provides a convenient synthesis of the corresponding (E)-alpha-chloroalkylidene-beta-lactams with high ee values. The structure and the stereochemistry of the products were established by the X-ray single-crystal diffraction study of (E)-6d and (E)-6e, which indicates that the stereoselectivity in this reaction is different from what was observed with propargylic alcohols. A rationale for this reaction was proposed.

  DOI：

  10.1021/jo0480996
• 作为产物：
  描述：

  1-己炔 在 N-甲基麻黄碱 、 zinc trifluoromethanesulfonate 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 (S)-1-ethyl-2-heptynyl methanesulfonate
  参考文献：
  名称：

  PdCl₂-Catalyzed Efficient Transformation of Propargylic Amines to (E)-α-Chloroalkylidene-β-lactams

  摘要：

  The PdCl2-catalyzed cyclocarbonylation reaction of propargylic amines with CuCl2 and benzoquinone afforded (E)-alpha-chloroalkylidene-beta-lactams in moderate to good yields. The formation of the corresponding Z-isomers or five-membered products was not observed. The reaction of the readily available optically active propargylic amines provides a convenient synthesis of the corresponding (E)-alpha-chloroalkylidene-beta-lactams with high ee values. The structure and the stereochemistry of the products were established by the X-ray single-crystal diffraction study of (E)-6d and (E)-6e, which indicates that the stereoselectivity in this reaction is different from what was observed with propargylic alcohols. A rationale for this reaction was proposed.

  DOI：

  10.1021/jo0480996

文献信息

• Optically Active 2,3-Allenoates<i>via</i>Palladium-Catalyzed Carbonylation of Enantioenriched Propargylic Mesylates
  作者：Yuli Wang、Shengming Ma

  DOI：10.1002/adsc.201200910

  日期：2013.3.11

  Under mild conditions, optically active 2,3‐allenoates were synthesized from enantioenriched propargylic mesylates with moderate to excellent yields and high efficiency of chirality transfer by using palladium(0) bis(dibenzylideneacetone) (3 mol%) with (S)‐(−)‐5,5′‐bis(diphenylphosphino)‐4,4′‐bi‐1,3‐benzodioxole [(S)‐SEGPHOS] (3 mol%) as the catalyst and diammonium hydrogen phosphate (1.1 equiv .)

  在温和的条件下，使用钯（0）双（二苄叉基丙酮）（3 mol％）与（S）-（- ）-5,5'-双（二苯基膦基）-4,4'-bi-1,3-苯并二恶唑[（S）-SEGPHOS]（3 mol％）作为催化剂，磷酸氢二铵（1.1当量）作为催化剂根据。