(E)-(S)-5-[(E)-(S)-3-Acryloyloxy-4-methyl-5-(2-methyl-thiazol-4-yl)-pent-4-enoyloxy]-hex-2-enoic acid (1S,2R)-2-(4-methoxy-benzyloxy)-1-methyl-but-3-enyl ester | 913563-50-5

• 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: (E)-(S)-5-[(E)-(S)-3-Acryloyloxy-4-methyl-5-(2-methyl-thiazol-4-yl)-pent-4-enoyloxy]-hex-2-enoic acid (1S,2R)-2-(4-methoxy-benzyloxy)-1-methyl-but-3-enyl ester
• CAS: 913563-50-5
• 化学式: C₃₂H₃₉NO₈S
• 分子量: 597.73
• InChiKey: CGTNBAMPFATVOS-VHKXIOMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.93
• 重原子数：
  42.0
• 可旋转键数：
  17.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  110.25
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (E)-(S)-5-[(E)-(S)-3-Acryloyloxy-4-methyl-5-(2-methyl-thiazol-4-yl)-pent-4-enoyloxy]-hex-2-enoic acid (1S,2R)-2-(4-methoxy-benzyloxy)-1-methyl-but-3-enyl ester 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 重铬酸吡啶 、 水 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 25.5h， 生成 (7E,13E)-(4S,10S,16S)-10,16-Dimethyl-4-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-1,5,11-trioxa-cyclohexadeca-7,13-diene-2,6,9,12-tetraone
  参考文献：
  名称：

  Synthesis of Macrosphelides with a Thiazole Side Chain:  New Antitumor Candidates Having Apoptosis-Inducing Property

  摘要：

  Hybrid compounds of macrosphelides and epothilones, both of which are natural macrolides having a 16-membered skeleton, were designed and synthesized using a ring-closing metathesis (RCM) strategy. Some of these hybrids were found to exhibit notable apoptosis-inducing activity against human lymphoma cells with higher potency than parent natural macrosphelides, and to be a promising lead compound for development of a new antitumor agent.

  DOI：

  10.1021/ol061922v
• 作为产物：
  描述：

  (E)-(S)-5-Hydroxy-hex-2-enoic acid (1S,2R)-2-(4-methoxy-benzyloxy)-1-methyl-but-3-enyl ester 在 4-二甲氨基吡啶 、 水 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 85.0h， 生成 (E)-(S)-5-[(E)-(S)-3-Acryloyloxy-4-methyl-5-(2-methyl-thiazol-4-yl)-pent-4-enoyloxy]-hex-2-enoic acid (1S,2R)-2-(4-methoxy-benzyloxy)-1-methyl-but-3-enyl ester
  参考文献：
  名称：

  Synthesis of Macrosphelides with a Thiazole Side Chain:  New Antitumor Candidates Having Apoptosis-Inducing Property

  摘要：

  Hybrid compounds of macrosphelides and epothilones, both of which are natural macrolides having a 16-membered skeleton, were designed and synthesized using a ring-closing metathesis (RCM) strategy. Some of these hybrids were found to exhibit notable apoptosis-inducing activity against human lymphoma cells with higher potency than parent natural macrosphelides, and to be a promising lead compound for development of a new antitumor agent.

  DOI：

  10.1021/ol061922v