2-(benzo[d]thiazol-2-ylsulfonyl)-2-fluoro-N-methoxy-N-methylacetamide | 1149578-06-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-(benzo[d]thiazol-2-ylsulfonyl)-2-fluoro-N-methoxy-N-methylacetamide
• 英文别名: N-methoxy-N-methyl-(1,3-benzothiazol-2-ylsulfonyl)fluoroacetamide；2-(1,3-benzothiazol-2-ylsulfonyl)-2-fluoro-N-methoxy-N-methylacetamide
• CAS: 1149578-06-2
• 化学式: C₁₁H₁₁FN₂O₄S₂
• 分子量: 318.35
• InChiKey: QFABERLXYQSCCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-苄基哌啶酮 、 2-(benzo[d]thiazol-2-ylsulfonyl)-2-fluoro-N-methoxy-N-methylacetamide 在 caesium carbonate 作用下， 以 N,N-dimetyhylformamide 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.5h， 以59%的产率得到2-(1-benzylpiperidin-4-ylidene)-2-fluoro-N-methoxy-N-methylacetamide
  参考文献：
  名称：

  α-Fluorovinyl Weinreb Amides and α-Fluoroenones from a Common Fluorinated Building Block

  摘要：

  Synthesis and reactivity of N-methoxy-N-methyl-(1,3-benzothiazol-2-ylsulfonyl)fluoroacetamide, a building block for Julia olefination, is reported. This reagent undergoes condensation reactions with aldehydes and cyclic ketones to give alpha-fluorovinyl Weinreb amides. Olefination reactions proceed under mild, DBU-mediated conditions, or in the presence of NaH. DBU-mediated condensations proceed with either E- or Z-selectivity, depending upon reaction conditions, whereas NaH-mediated reactions are >= 98% Z-stereoselective. Conversion of the Weinreb amide moiety in N-methoxy-N-methyl-(1,3-benzothiazol-2-ylsulfanyl)fluoroacetamide to ketones, followed by oxidation, resulted in another set of olefination reagents, namely (1,3-benzothiazol-2-ylsulfonyl)fluoromethyl phenyl and propyl ketones. In the presence of DBU, these compounds react with aldehydes tested to give alpha-fluoroenones with high Z-selectivity. The use of N-methoxy-N-methyl-(1,3-benzothiazol-2-ylsulfanyl)fluoroacetamide as a common fluorinated intermediate in the synthesis of alpha-fluorovinyl Weinreb amides and alpha-fluoroenones has been demonstrated. Application of the Weinreb amide to alpha-flu-fluoro allyl amine synthesis is also shown.

  DOI：

  10.1021/jo802784w
• 作为产物：
  描述：

  N-methoxy-N-methyl-(1,3-benzothiazol-2-ylsulfanyl)fluoroacetamide 在 chromium(VI) oxide 、 高碘酸 作用下， 以 乙腈 为溶剂， 以82%的产率得到2-(benzo[d]thiazol-2-ylsulfonyl)-2-fluoro-N-methoxy-N-methylacetamide
  参考文献：
  名称：

  α-Fluorovinyl Weinreb Amides and α-Fluoroenones from a Common Fluorinated Building Block

  摘要：

  Synthesis and reactivity of N-methoxy-N-methyl-(1,3-benzothiazol-2-ylsulfonyl)fluoroacetamide, a building block for Julia olefination, is reported. This reagent undergoes condensation reactions with aldehydes and cyclic ketones to give alpha-fluorovinyl Weinreb amides. Olefination reactions proceed under mild, DBU-mediated conditions, or in the presence of NaH. DBU-mediated condensations proceed with either E- or Z-selectivity, depending upon reaction conditions, whereas NaH-mediated reactions are >= 98% Z-stereoselective. Conversion of the Weinreb amide moiety in N-methoxy-N-methyl-(1,3-benzothiazol-2-ylsulfanyl)fluoroacetamide to ketones, followed by oxidation, resulted in another set of olefination reagents, namely (1,3-benzothiazol-2-ylsulfonyl)fluoromethyl phenyl and propyl ketones. In the presence of DBU, these compounds react with aldehydes tested to give alpha-fluoroenones with high Z-selectivity. The use of N-methoxy-N-methyl-(1,3-benzothiazol-2-ylsulfanyl)fluoroacetamide as a common fluorinated intermediate in the synthesis of alpha-fluorovinyl Weinreb amides and alpha-fluoroenones has been demonstrated. Application of the Weinreb amide to alpha-flu-fluoro allyl amine synthesis is also shown.

  DOI：

  10.1021/jo802784w

文献信息

• Synthesis of Regiospecifically Fluorinated Conjugated Dienamides
  作者：Mohammad Chowdhury、Samir Mandal、Shaibal Banerjee、Barbara Zajc

  DOI：10.3390/molecules19044418

  日期：——

  Modular synthesis of regiospecifically fluorinated 2,4-diene Weinreb amides, with defined stereochemistry at both double bonds, was achieved via two sequential Julia-Kocienski olefinations. In the first step, a Z-α-fluorovinyl Weinreb amide unit with a benzothiazolylsulfanyl substituent at the allylic position was assembled. This was achieved via condensation of two primary building blocks, namely

  通过两个连续的 Julia-Kocienski 烯化实现了区域特异性氟化 2,4-二烯 Weinreb 酰胺的模块化合成，在双键上具有明确的立体化学。在第一步中，组装了在烯丙基位置具有苯并噻唑硫烷基取代基的 Z-α-氟乙烯基 Weinreb 酰胺单元。这是通过两个主要结构单元的缩合实现的，即 2-(苯并[d]噻唑-2-基磺酰基)-2-氟-N-甲氧基-N-甲基乙酰胺（一种 Julia-Kocienski 烯化试剂）和 2-(苯并[d]噻唑-2-基磺酰基)-2-氟-N-甲氧基-N-甲基乙酰胺[d]thiazol-2-ylthio) 乙醛（一种双功能结构单元）。这种缩合具有高度的 Z 选择性并且以 76% 的良好产率进行。苯并噻唑硫烷基部分的氧化提供了第二代 Julia-Kocienski 烯化试剂，它用于通过 DBU 介导的与醛的缩合引入第二个烯键，以 50%–74% 的产率得到 (2Z,4E/Z)-二烯酰胺。尽管烯化是
• Diversely C8-functionalized adenine nucleosides <i>via</i> their underexplored carboxaldehydes
  作者：Hari K. Akula、Suyeal Bae、Padmanava Pradhan、Lijia Yang、Barbara Zajc、Mahesh K. Lakshman

  DOI：10.1039/d1cc06686b

  日期：——

  underexploited for C8 modifications of these nucleosides. Only in situ formation of 8-formyladenosine is known and a single application of an N-benzoyl derivative has been reported. On the other hand, 8-formyl-2′-deoxyadenosine and its applications remain unknown. Herein, we report straightforward, scalable syntheses of both N-unprotected 8-formyladenine nucleoside derivatives, and demonstrate broad diversification

  腺苷和 2'-脱氧腺苷的潜在用途广泛的N-未保护 8-甲酰基衍生物在这些核苷的 C8 修饰方面开发不足。只有8-甲酰腺苷的原位形成是已知的，并且已经报道了N-苯甲酰基衍生物的单一应用。另一方面，8-甲酰基-2'-脱氧腺苷及其应用仍然未知。在这里，我们报告了两种N-未保护的 8-甲酰腺嘌呤核苷衍生物的直接、可扩展的合成，并通过羟甲基化、叠氮化、CuAAC 连接、还原胺化以及改性 Julia 和霍纳的烯化和氟烯化证明了 C8 位的广泛多样化–Wadsworth–Emmons 试剂。
• α-Fluorovinyl Weinreb Amides and α-Fluoroenones from a Common Fluorinated Building Block
  作者：Arun K. Ghosh、Shaibal Banerjee、Saikat Sinha、Soon Bang Kang、Barbara Zajc

  DOI：10.1021/jo802784w

  日期：2009.5.15

  Synthesis and reactivity of N-methoxy-N-methyl-(1,3-benzothiazol-2-ylsulfonyl)fluoroacetamide, a building block for Julia olefination, is reported. This reagent undergoes condensation reactions with aldehydes and cyclic ketones to give alpha-fluorovinyl Weinreb amides. Olefination reactions proceed under mild, DBU-mediated conditions, or in the presence of NaH. DBU-mediated condensations proceed with either E- or Z-selectivity, depending upon reaction conditions, whereas NaH-mediated reactions are >= 98% Z-stereoselective. Conversion of the Weinreb amide moiety in N-methoxy-N-methyl-(1,3-benzothiazol-2-ylsulfanyl)fluoroacetamide to ketones, followed by oxidation, resulted in another set of olefination reagents, namely (1,3-benzothiazol-2-ylsulfonyl)fluoromethyl phenyl and propyl ketones. In the presence of DBU, these compounds react with aldehydes tested to give alpha-fluoroenones with high Z-selectivity. The use of N-methoxy-N-methyl-(1,3-benzothiazol-2-ylsulfanyl)fluoroacetamide as a common fluorinated intermediate in the synthesis of alpha-fluorovinyl Weinreb amides and alpha-fluoroenones has been demonstrated. Application of the Weinreb amide to alpha-flu-fluoro allyl amine synthesis is also shown.