4-Benzyloxy-but-2-ynoic acid 4-nitro-benzyl ester | 502918-02-7

• 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: 4-Benzyloxy-but-2-ynoic acid 4-nitro-benzyl ester
• 英文别名: (4-Nitrophenyl)methyl 4-(benzyloxy)but-2-ynoate；(4-nitrophenyl)methyl 4-phenylmethoxybut-2-ynoate
• CAS: 502918-02-7
• 化学式: C₁₈H₁₅NO₅
• 分子量: 325.321
• InChiKey: UBFHGIIMKBNXEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-Benzyloxy-but-2-ynoic acid 4-nitro-benzyl ester 、 (Rs,1R,2S,3R)-2-methoxy-3-(3,3-dimethyl-1-butynylsulfinyl)bornane 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 diethylzinc 作用下， 以 1,4-二氧六环 为溶剂， 生成 4-nitrobenzyl (E)-4-benzyloxy-3-[[(Ss,1R,2S,3R)-2-methoxybornane-3-yl]sulfinyl]-2-butenoate 、 4-nitrobenzyl (E)-4-benzyloxy-3-[[(Rs,1R,2S,3R)-2-methoxybornane-3-yl]sulfinyl]-2-butenoate
  参考文献：
  名称：

  Maezaki, Naoyoshi; Yagi, Suguru; Ohsawa, Shizuka, Tetrahedron Asymmetry, 2002, vol. 13, # 18, p. 1960 - 1964

  摘要：

  DOI：

文献信息

• Synthesis of chiral vinylic sulfoxides by Pd-catalyzed asymmetric sulfinylzincation
  作者：Naoyoshi Maezaki、Suguru Yagi、Shizuka Ohsawa、Hirofumi Ohishi、Tetsuaki Tanaka

  DOI：10.1016/j.tet.2003.10.037

  日期：2003.12

  Novel asymmetric sulfinylzincation of alkynoates has been accomplished via a Pd-catalyzed sulfinylzincation using 1-alkynyl sulfoxides bearing chiral auxiliaries as a sulfinylating reagent. The reaction proceeded in a highly syn-selective fashion, giving the (E)-beta-sulfinyl alpha,beta-unsaturated ester exclusively. Among the chiral sulfinylating reagents tested, an isoborneol-type compound (Rs)-4 showed the best results in terms of both yield and diastereoselectivity. As a result of optimization of the reaction, the selectivity was improved up to 92:8 dr, and stereochemistry of the newly formed sulfur stereogenic center was revealed as (Ss)-configuration. (C) 2003 Elsevier Ltd. All rights reserved.