Ethyl 8-(4-bromobenzoyl)-1,5-diethyl-2,3-dimethyl-5-phenylfuro[3,2-e][1,4]thiazepine-7-carboxylate | 1005385-90-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Ethyl 8-(4-bromobenzoyl)-1,5-diethyl-2,3-dimethyl-5-phenylfuro[3,2-e][1,4]thiazepine-7-carboxylate
• CAS: 1005385-90-9
• 化学式: C₂₉H₃₀BrNO₄S
• 分子量: 568.532
• InChiKey: PVTXYAYVBPZMHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  85
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ethyl 8-(4-bromobenzoyl)-1,5-diethyl-2,3-dimethyl-5-phenylfuro[3,2-e][1,4]thiazepine-7-carboxylate 、 2-(三甲基硅)苯基三氟甲烷磺酸盐 在 cesium fluoride 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以88%的产率得到ethyl 6-(4-bromobenzoyl)-1,5-diethyl-3,4-dimethyl-1-phenyl-1H-7,11b-epoxynaphtho[2,1-e][1,4]thiazepine-7(5H)-carboxylate
  参考文献：
  名称：

  Thiazepine moiety-controlled regioselective rearrangements of 7-oxanorbornadiene derivatives

  摘要：

  我们发现了由硫氮杂环庚烷分子控制的 7-氧杂冰片二烯衍生物（2、7 和 12）的区域选择性骨架重排，在布氏酸存在下具有高区域选择性和/或非对映选择性。

  DOI：

  10.1039/b813371a
• 作为产物：
  描述：

  溴化3-乙基-4,5-二甲基-1,3-噻唑-3-正离子 、 2-苯基-1-丁烯-1-酮 、 4-(4-bromophenyl)-4-oxo-but-2-ynoic acid ethyl ester 在 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 以38%的产率得到Ethyl 8-(4-bromobenzoyl)-1,5-diethyl-2,3-dimethyl-5-phenylfuro[3,2-e][1,4]thiazepine-7-carboxylate
  参考文献：
  名称：

  Concise Assembly of Highly Substituted Furan-Fused 1,4-Thiazepines and Their Diels−Alder Reactions with Benzynes

  摘要：

  A facile and highly efficient three-component reaction of thiazole or benzothiazole carbenes, disubstituted ketenes, and activated alkynes is disclosed. With this methodology, a polysubstituted ring system containing furo[2,3-c]thiazepine core can be constructed from simple and readily accessible starting materials in good yields. The scope and limitation of this transformation were investigated in detail by using various thiazole carbene, ketene, and alkyne components. Furthermore, the synthetic utilities of these unique polyheterocyclic compounds were demonstrated via their Diels-Alder reactions with benzynes to furnish thiazepine-fused 7-oxanorbornadiene derivatives in excellent yields.

  DOI：

  10.1021/jo702299m

文献信息

• Thiazepine moiety-controlled regioselective rearrangements of 7-oxanorbornadiene derivatives
  作者：Hanfeng Ding、Yiping Zhang、Weijun Yao、Duanjun Xu、Cheng Ma

  DOI：10.1039/b813371a

  日期：——

  We have discovered thiazepine moiety-controlled regioselective skeletal rearrangements of 7-oxanorbornadiene derivatives (2, 7 and 12) with high regioselectivity and/or diastereoselectivity in the presence of Brønsted acid.

  我们发现了由硫氮杂环庚烷分子控制的 7-氧杂冰片二烯衍生物（2、7 和 12）的区域选择性骨架重排，在布氏酸存在下具有高区域选择性和/或非对映选择性。
• Concise Assembly of Highly Substituted Furan-Fused 1,4-Thiazepines and Their Diels−Alder Reactions with Benzynes
  作者：Hanfeng Ding、Yiping Zhang、Ming Bian、Weijun Yao、Cheng Ma

  DOI：10.1021/jo702299m

  日期：2008.1.1

  A facile and highly efficient three-component reaction of thiazole or benzothiazole carbenes, disubstituted ketenes, and activated alkynes is disclosed. With this methodology, a polysubstituted ring system containing furo[2,3-c]thiazepine core can be constructed from simple and readily accessible starting materials in good yields. The scope and limitation of this transformation were investigated in detail by using various thiazole carbene, ketene, and alkyne components. Furthermore, the synthetic utilities of these unique polyheterocyclic compounds were demonstrated via their Diels-Alder reactions with benzynes to furnish thiazepine-fused 7-oxanorbornadiene derivatives in excellent yields.